Category Archives: Chicago Tips & Tricks

Chicago Nicknames

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Chicago Nicknames: The Complete Guide (Updated for 2025)

Chicago, with its rich history and cultural significance, has earned many nicknames over the decades. From “The Windy City” to lesser-known monikers like “Chiberia,” each nickname tells a fascinating story about the city’s character and evolution. This comprehensive guide explores the origins and meanings behind Chicago’s most famous nicknames.

Where Did ‘Chicago’ Come From?

Before diving into nicknames, let’s address the origin of “Chicago” itself. The city’s name derives from a Native American word “shikaakwa” (pronounced “shi-KAA-kwa”), used by the Miami and Illinois tribes to describe the wild leeks or ramps that grew abundantly along the Chicago River.

These pungent vegetables, similar to onions and garlic, gave the area a distinctive smell. French explorers in the 1600s adapted this word, and over time, “shikaakwa” evolved into “Chicago.” So at its core, our magnificent city is named after what early settlers might have called a “stinky onion” plant!

The Windy City

Origin: Late 19th century
Still relevant today? Absolutely – this remains Chicago’s most recognized nickname

While many visitors assume this nickname refers to Chicago’s blustery weather conditions off Lake Michigan, the historical evidence points to more colorful origins.

The Cincinnati Rivalry Theory

One compelling theory traces back to the intense rivalry between Chicago and Cincinnati in the mid-19th century. Both cities competed fiercely for economic dominance, particularly in the meatpacking industry. Cincinnati held the title “Porkopolis” until the 1860s when Chicago surpassed it as America’s leading pork processor.

The rivalry extended beyond business to baseball, with Chicago introducing the White Stockings specifically to compete with the Cincinnati Red Stockings. Newspapers of the era, including the Cincinnati Enquirer, began referring to Chicago as “the Windy City” as early as 1876. The term was likely a dual reference to both Chicago’s weather and its supposedly boastful citizens.

The World’s Fair Theory

Perhaps the more widely accepted explanation connects the nickname to Chicago’s aggressive campaign to host the 1893 World’s Columbian Exposition. Chicago lobbied extensively against New York and other major cities for the honor.

Charles Dana, editor of the New York Sun, allegedly warned people to ignore “the nonsensical claims of that windy city” during this campaign. While this specific quote has never been definitively verified in print from that period, it’s certain that rivals viewed Chicago’s promotional efforts as excessive “hot air.”

Chicago ultimately won the bid to host the fair, which became one of the most significant events in the city’s history. The successful exposition demonstrated that Chicago could deliver on its grand promises – windy talk backed by impressive action.

Second City

Origin: Early 20th century
Still relevant today? Yes, though Chicago is now the third-largest U.S. city

The “Second City” nickname has multiple origin stories, each reflecting different aspects of Chicago’s history.

After the Great Chicago Fire

Following the devastating Great Chicago Fire of 1871, Chicago faced the monumental task of rebuilding. Rather than merely restoring what was lost, city planners and architects seized the opportunity to reimagine urban design. The “second” Chicago that emerged from the ashes featured innovative steel-frame skyscrapers, improved infrastructure, and forward-thinking urban planning.

This extraordinary renaissance represents one of the most remarkable periods of urban development in world history. Within two decades, Chicago transformed itself from a burned-out shell to a global architectural showcase. In this sense, modern Chicago is literally the “second city” built on the same site.

Second to New York

The more commonly cited explanation relates to Chicago’s historical position as the second-most populous city in the United States, behind New York. This status became cemented in popular culture with A.J. Liebling’s somewhat unflattering 1952 book, “Chicago: The Second City,” which portrayed Chicago as perpetually in New York’s shadow.

Chicago held this second-place population ranking from 1890 until 1984, when Los Angeles surpassed it. Despite now being the third-largest U.S. city (with New York at 8.1M residents, Los Angeles at 3.7M, and Chicago at 2.7M), the nickname persists.

Cultural Impact

In 1959, the groundbreaking comedy theater and school “The Second City” adopted this nickname, embracing it with self-deprecating humor. This world-famous institution has launched the careers of countless comedy legends like Bill Murray, Tina Fey, and Stephen Colbert, transforming a once-derogatory term into a badge of cultural innovation.

City of Big Shoulders

Origin: 1914
Still relevant today? Yes, particularly in marketing and civic pride

This evocative nickname comes directly from Carl Sandburg’s iconic 1914 poem “Chicago,” which begins:

“Hog Butcher for the World,
Tool Maker, Stacker of Wheat,
Player with Railroads and the Nation’s Freight Handler;
Stormy, husky, brawling,
City of the Big Shoulders.”

Sandburg’s powerful imagery captured Chicago’s industrial might and the resilient spirit of its working-class residents. The phrase resonated because it perfectly encapsulated Chicago’s identity as a city built on physical labor and gritty determination.

The “big shoulders” metaphor also alludes to how Chicago literally raised itself. In an extraordinary engineering feat during the 1850s and 1860s, the city elevated entire blocks by 4-14 feet to improve drainage and create a proper sewer system. After the Great Fire, Chicago rebuilt with a multi-level design, creating the underground service areas that still exist today beneath the Loop.

Chi-Town

Origin: Early 1900s
Still relevant today? Commonly used in popular culture, though some locals resist it

“Chi-Town” (pronounced “shy-town”) represents a more casual, contemporary nickname that gained prominence through popular culture. The term follows a common pattern of shortening a city’s name and adding “-town,” similar to “H-Town” for Houston or “D-Town” for Detroit.

While its exact origins remain unclear, “Chi-Town” became firmly established in American vernacular through music, particularly hip-hop and R&B. Chicago native Kanye West helped popularize the term with his 2007 song “Homecoming,” which features the lyrics “I met this girl when I was three years old, and what I loved most, she had so much soul… She said you left your city for another woman… If you really loved me you would stick around.”

The nickname elicits mixed reactions from Chicagoans. Some embrace it as a term of endearment, while others consider it inauthentic or primarily used by tourists and outsiders. This debate reflects the complex relationship many cities have with nicknames that emerge from popular culture rather than historical events.

Newer Nicknames

Chiberia

Origin: 2014
Still relevant today? Used seasonally during extreme cold snaps

This relatively recent nickname gained prominence during the brutal winter of 2014, when Chicago experienced record-breaking cold temperatures. Meteorologist Richard Castro coined the term “Chiberia,” a clever portmanteau of “Chicago” and “Siberia,” to describe the arctic-like conditions.

The name caught on quickly through social media and news reports, with the National Weather Service even using the hashtag #Chiberia. When temperatures plunged to -16°F (-27°C) with wind chills reaching -42°F (-41°C), the comparison to the remote, frigid regions of Siberia seemed entirely appropriate.

Chicagoans, known for their resilience in the face of harsh weather, embraced the nickname with characteristic dark humor. “I survived Chiberia” merchandise appeared throughout the city, and the term has resurfaced during subsequent extreme cold snaps.

Chiraq

Origin: Early 2010s
Still relevant today? Controversial but still used in certain contexts

Perhaps the most controversial of Chicago’s nicknames, “Chiraq” combines “Chicago” and “Iraq” to draw attention to the city’s struggles with gun violence. The term emerged from Chicago’s drill music scene in the early 2010s and gained wider recognition through Spike Lee’s 2015 film of the same name.

The nickname remains deeply divisive. Critics argue it sensationalizes violence and unfairly stigmatizes entire communities, particularly on the South and West Sides. Supporters contend it brings necessary attention to serious issues facing parts of the city that are often overlooked in discussions about Chicago’s prosperity.

Many community activists and local leaders have pushed back against the term, preferring to focus on Chicago’s resilience and the positive work being done in neighborhoods affected by violence.

Lesser-Known Chicago Nicknames

City in a Garden (Urbs in Horto)

Chicago’s official motto, “Urbs in Horto,” is Latin for “City in a Garden.” Adopted in the 1830s, this phrase highlights Chicago’s commitment to green spaces and urban planning. The city’s extensive park system, including Grant Park, Lincoln Park, and the 18-mile Lakefront Trail, reflects this garden-city vision.

The City That Works

Made famous by Mayor Richard J. Daley in the 1970s, this nickname celebrates Chicago’s pragmatic, blue-collar ethos. It portrayed Chicago as a place where things get done, in contrast to cities perceived as all talk and no action. The phrase captured the city’s industrial heritage and its residents’ strong work ethic.

Paris on the Prairie

This elegant nickname emerged following Daniel Burnham’s influential 1909 “Plan of Chicago,” which envisioned the city with grand boulevards, parks, and civic spaces inspired by European capitals. The World’s Columbian Exposition of 1893 showcased this vision with its “White City” of neoclassical buildings, establishing Chicago as a center for architectural innovation.

The 312

Named after Chicago’s original area code, “The 312” refers primarily to downtown Chicago. As the city grew, additional area codes (773, 872, 708) were added, making 312 numbers increasingly rare and associated specifically with the heart of the city.

Mud City

Possibly Chicago’s oldest nickname, “Mud City” describes the notoriously muddy conditions of early Chicago before modern infrastructure. The marshy terrain was so challenging that buildings needed to be physically raised to implement proper drainage systems.

The Third Coast

This nickname acknowledges Chicago’s position on Lake Michigan and its historical importance as a port city. It places Chicago’s lakefront in the same conversation as America’s Atlantic and Pacific coasts, recognizing the Great Lakes’ significance to shipping and commerce.

Chicago Nicknames: A Comparison Table

Nickname Origin Time Period Still Used? Locally Accepted?
The Windy City Rivalry with Cincinnati/World’s Fair campaign 1870s-1890s Widely Yes
Second City Post-fire rebuilding/Population ranking Early 1900s Commonly Yes
City of Big Shoulders Carl Sandburg’s poem 1914 In marketing Yes
Chi-Town Popular culture Early 1900s In media Mixed
Chiberia Extreme winter weather 2014 Seasonally Yes, humorously
Chiraq Drill music scene 2010s Limited Controversial
City in a Garden City motto 1830s Officially Yes
The City That Works Mayor Richard J. Daley 1970s In civic contexts Yes

What Chicagoans Really Call Their City

While visitors and media outlets frequently use these colorful nicknames, many Chicago residents simply call it “Chicago” or “the city.” Locals might refer to specific neighborhoods (“the South Side,” “Logan Square,” “Pilsen”) rather than using nicknames for the entire city.

That said, “The Windy City” remains widely embraced by both locals and visitors, appearing on everything from T-shirts to official tourism materials.

Experience Chicago’s Nicknames in Person

Each of these nicknames represents a different facet of Chicago’s rich and complex character. From the architectural wonders that rose after the Great Fire to the windswept streets along the lakefront, these nicknames come to life when you explore the city in person.

Join us on our Chicago walking tours where our knowledgeable guides will share even more stories about how these nicknames shaped the city you see today. Our Crime and Gangster Tour especially highlights the gritty history behind some of Chicago’s most notorious reputations!

Share Your Chicago Nickname Stories

Do you have a favorite Chicago nickname we missed? Perhaps you’ve heard a unique variation or have a personal story about how these nicknames shaped your perception of the city? Share your thoughts in the comments below!

This article was last updated on March 8, 2025, with additional historical research and contemporary context. Want to hear more fascinating Chicago stories? Book one of our walking tours to explore the city with expert local guides who bring these nicknames and their history to life!

 

 

 

20 Free Things to do in Chicago

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Keeping with the spirit of our business and our desire to help everyone enjoy Chicago on the tightest of budgets we’ve compiled a list of the 20 best free things to do in Chicago.

#1 goes to … Visit Navy Pier – tough to beat the action at Navy Pier during the summer. It’s a real special treat if you’re there for the 4th of July too, great fireworks show.

2. Take a walking tour – Yup, a shameless plug. But really – they’re awesome. Check out our calendar and reserve your spot today.

3. Chicago Cultural Center – One of the first cultural centers in the nation is home to the largest Tiffany glass dome and rotating art exhibits – all free of charge.

4. Millennium Park – your visit to Chicago is not complete unless you visit The Bean and Crown Fountain – both located within a hop, skip and a jump of each other in Millennium Park.

5. Buckingham Fountain – Where are our Married with Children fans? No? Ok… Well, still – definitely worth a visit during the summer when the fountains are on. (April – October, 8am – 11pm daily)

6. Chicago Botanic Gardens – the gardens are located just outside the city. Entrance is free, but parking is not. We’re not entirely sure if this should even be on our list. It is stunningly beautiful though.

7. Chicago Museum of Contemporary Art – This is another tricky one. Technically this is a pay-what-your-want museum. The suggested admission fee is $12 for an adult but they will not turn anyone away.

8. Arcade – Yes, you have read that right. There are a handful of bars popping up across the city that allow you to play your favorite games, like NBA Jam, for free. Headquarters Beercade in Lakeview is one of them.

9. Visit a Chicago brewery. Both Lagunitas and Revolution offer free tours.

10. Take advantage of Chicago’s 18 miles of lake front trail. Ride a bike, walk, jog, people watch, segway (probably not free) or rollerblade. Just take advantage of the trail!

11. Lincoln Park Conservatory – Love love love this place. Their rotating show room is awesome as is their fern garden. Don’t forget that the Lincoln Park Conservatory is only the 2nd largest in Chicago behind the Garfield Park Conservatory which is also free.

12. Harold Washington Library – it’s gigantic, has wi-fi and is a great spot to escape the hustle and bustle of the city while your still in the city.

13. Movies in Millennium Park – Every Tuesday beginning June 21 you can catch a flick in Millennium Park. Here is the full line up of what’s playing.

14. National Museum of Mexican Art – The museum has over 9,000 pieces making it on of the largest collections of Mexican art in the country.

15. Maggie Daley Park – Visit Chicago’s version of Alice in Wonderland and unleash your inner child.

16. The Rookery Building – The lobby of this building has the only Frank Lloyd Wright design in the Loop. Do not miss this if that’s your type of thing.

17. Lincoln Park Zoo – the largest urban zoo in America. Home to more than 200 different species and over 1,000 animals.

18. Jane Adams Hull-House Museum – Dedicated to the first woman to win the Nobel Prize.

19. The Underground Pedway – sure, it’s not really a match for Minneapolis’ covered walkways, but the Chicago version is kind of cool if you have a chance to dip below the surface.

20. John Hancock Observation Deck – save yourself the $20 or so to go to the deck and instead head to the Signature Lounge located on the 96th floor. It’s free and you can enjoy a cocktail up there!

What did we miss? Let us know your favorite free thing to do in Chicago.

The Best Chicago Museums

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There are no shortages of museums in Chicago. According to Trip Advisor there are 98 of them in fact. Locals who have spent their entire lives in Chicago will probably never make it to even half of them. So how the heck can you narrow the best Chicago museums? Our museum experts have picked the top destination from a handful of categories.

Chicago Art Museums

We’ll start with the easiest category. Hands down, the best art museum in the Windy City is the Art Institute of Chicago. To be honest, it is one of the best in the world. Trip Advisor has repeatedly lavished awards on it, such as Best Museum, and a Top Ten Traveler’s Choice Award. It is clear to see why. The museum features permanent collections that include the world’s masters, such as Monet, Da Vinci, Van Gogh, Manet, and Rembrandt, just to name a few. “American Gothic” makes its home here, and from ancient to contemporary, practically every school is represented. The Thorne Rooms are one unique feature of the Institute that entice both young and old. Perfectly to scale, these miniature rooms each reflect a different time period. Together, the Rooms constitute a dollhouse that is like no other. An interesting note, Illinois author Marianne Malone has written best-selling children’s fiction based on the Thorne Rooms. If you have little ones, have them read the book before their visit.

Runner up: And if for some reason you can’t get to the Art Institute, try the Museum of Contemporary Art. It too, is fantastic, and free tours are given daily. And we like free.

Website: http://www.artic.edu

Hours: Open daily 10:30am–5:00pm, Thursdays until 8:00pm

Cost: $25 adults, $19 students or seniors, FREE for Children under 14 and Illinois residents on Thursdays

Real Good News: The Art Institute of Chicago is included in the Chicago CityPass which saves you up to 53% off regular priced admission.

Chicago Science Museums

Source: Shedd Aquarium

Source: Shedd Aquarium

If you’re a science lover, Chicago has much to offer in the way of museums. A place that really wows is the Shedd Aquarium. One of the largest inland aquariums in the world, the Shedd has over 30,000 animals—fresh water, marine, and even terrestrial. That means that in addition to getting an up-close view of sharks, sea lions, and octopi, you’ll also see some animals that dwell on the ground, like monkeys, frogs, and iguanas. The Aquarium offers all kinds of tours, from basic admission to small group “behind the scene” tours that are phenomenal. You’ll see where expert veterinarians and trainers care for our aquatic friends. And what care it is—the freshest of seafood from all over the world comes to Chicago to be served in the finest restaurants… and at the Shedd. But you can’t get it at the cafeteria. It’s for the aquarium’s permanent residents! You can however, enjoy some of Chicago’s finest Jazz here. Every Wednesday (begins June 22) in the summer “Jazzin’ at the Shedd” features popular Jazz artists, dinner, and cocktails on their spacious veranda, plus a great view of the fireworks that start at dusk. Before it gets dark though, take in the awesome architectural show that is the outside of the Shedd Aquarium.

Runner up: Another great science museum is in Chicago’s Hyde Park neighborhood, so if you are more for physics and trains than dolphins and coral, visit the Museum of Science & Industry instead – or heck, visit both!

Website: http://www.sheddaquarium.org

Hours: Open daily 9:00am–5:00pm, Weekends open until 6:00pm

Cost: There are so many ticketing options (group size, what do you want to see, buy in advance). The cheapest option starts at $37.95 for adults and $28.95 for children by purchasing tickets online.

Real Good News: The Art Institute of Chicago is included in the Chicago CityPass which saves you up to 53% off regular priced admission.

Chicago History Museums

Sharing a campus with the Shedd Aquarium and the Adler Planetarium is the Field Museum of Natural History. It is another Windy City Gem. You’ll marvel at colossal “Sue”, prominently displayed on its main floor. She is the most well-preserved and complete Tyrannosaurus Rex ever discovered. The children’s area, where the little ones can excavate finds of their own is a big draw. Through the museum’s partnership with University of Chicago Paleontologist Paul Sereno (once voted one of the world’s most beautiful people by People Magazine) the dinosaur exhibits are as fun as they are educational. The Museum frequently hosts temporary exhibits (a recent one on Haitian Voodoo was a real crowd-pleaser) that are as interesting as their permanent offerings. The Museum building itself is extraordinary—it is often rented for large affairs due to its beauty. Come in the warm months and you can have a lovely picnic on the adjoining lawn, fly a kite, or watch as children roll down the small hills at the front of the building.

Runner up: If you’re interested in cultural as opposed to natural history, you may want to visit the Chicago History Museum. Though it is quite a bit smaller, it’s chockfull of interesting facts on America’s Second City.

Website: https://www.fieldmuseum.org

Hours: Open daily 9:00am–5:00pm, except Christmas day. Last admission is 4pm.

Cost:  Adults $38, students & seniors $32, Children (3-11) $26

Real Good News: The Art Institute of Chicago is included in the Chicago CityPass which saves you up to 53% off regular priced admission.

Chicago Children’s Museums

Source: Chicago Children's Museum

Source: Chicago Children’s Museum

As if Navy Pier weren’t enough of a playground, with its huge ferris wheel, funhouse, and stage, the Chicago Children’s Museum is housed on its second through fourth floors. While you might wish to take the stairs, tykes usually prefer to climb up through the burlap-netted maze. A family with young one’s could easily spend the whole day at this museum, which is completely hands-on. It features an extensive water exhibit (be sure to don one of the raincoats provided) as well as a miniature grocery store entirely manned by its short-in-stature visitors. In one room, glass boxes adorn the walls with games and toys of yesteryear that will have parents waxing nostalgic. There are also plenty of child-friendly dining and shopping options on the first floor of the Pier, from sit-down restaurants to McDonalds, and a great ice cream shop. Don’t miss the Build-a-Bear Workshop either.

Runner up: For those who like a less crowded, lower-key experience, The Kohl Children’s Museum in nearby Glenview is equally splendid.

Website: http://www.chicagochildrensmuseum.org

Hours: Open daily 9:00am–5:00pm, Thursdays open until 8:00pm

Cost:  Children & Adults $14, Seniors $13, Children under 1yr old FREE. There are a variety of discounts and specials available. Make sure to visit their Plan your Visit page for details.

Free Chicago Museums

No way we can do this post without mentioning the best free museums in the city.

Chicago is a city whose large and thriving Mexican population is manifested in its food and art. The Pilsen neighborhood is the epicenter of this community. In it lies one of the largest collections of Mexican art in the country, at the National Museum of Mexican Art. With over 9,000 pieces housed in a spacious and modern facility, it’s a shock that this museum is free to the public. Yet since its inception in 1987, the Museum has remained true to its mission of bringing Mexican art and culture to the masses “sin fronteras” (without borders). In addition to the fine art that is part of the collection, you can also see a host of cultural and entertainment events here, from dance performances to speeches. Some say that the gift shop offers such unique and authentic wares that it is an exhibit itself. When you’re finished at the museum, be sure to stay in the neighborhood and enjoy delicious, reasonably priced Mexican food, along with some tequila or a margarita that will having you screaming for “uno mas”!

Runner up: If you can’t make it to the NMMA, the University of Chicago’s Oriental Museum is another outstanding free cultural venue that has the additional benefit of featuring an entombed body!

Website: http://www.nationalmuseumofmexicanart.org

Hours: Tuesday – Sunday 10:00am – 5:00pm. Closed Mondays and on major holidays.

Cost:  Free!

Chicago Planetary & Observatory Museums

Source: Adler Planetarium

Source: Adler Planetarium

Ok, maybe we lied earlier – this is probably the easiest category to pick our favorite in because there is really only one!

If you want to stare into space from Chicago, head straight for the Adler Planetarium, where the “star” is the Doane Observatory. Here, the telescope allows viewers to see planets that are trillions of miles away. Visitor’s come to experience this as well as the phenomenal IMAX theater at the planetarium, which also presents some thrilling footage of the universe. Another draw of the Adler Planetarium is its extensive collection. From scientific instruments of historical significance, to paintings, photographs, and books, even the most advanced researchers will not be disappointed. For those who can’t get to the Adler, neighboring Evanston has a formidable competitor. Northwestern University’s Dearborn Observatory has an 18.5 inch refracting telescope that is open to the public.

Website: http://www.adlerplanetarium.org

Hours: Open daily 9:30am–4:00pm, weekends open until 4:30pm

Cost:  General admission for adults start at $12 and $8 for children. (Note: these prices do not include any shows which are pretty cool)

Real Good News: The Art Institute of Chicago is included in the Chicago CityPass which saves you up to 53% off regular priced admission.

Chicago Specialty Museums

The Pullman Museum and Historic District is a designated National Historic Site that is as much a neighborhood as it is a museum. The district on the south side of Chicago features buildings such as the Arcade, the Clock Tower, the Market, and row homes. It is a tribute to Pullman’s influence on American industry, showing how manufacturing generated large and thriving communities. The row homes are actual former residences of people that were employed at the Pullman textile mill and other facilities. Period furniture and architecture is expertly preserved. The library features books on the history of the area and blueprints that were integral to its construction. Visiting this extensive historic site will take all day or more. If you can’t make it down to the south side to experience it, you might want to visit the Museum of Contemporay Photography instead. This is a top-notch specialty museum located right in the loop. Best of all, it’s free!

So there you have it – our curated museum list to help plan your next visit. If you think that we should have included different museums let our guests know by leaving a comment below!

 

 

 

 

Forgot Something? Don’t Worry, Chicago Delivers within 2 Hours

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We’ve all been there – no matter how much time and care you take while packing you arrive at your hotel (or Airbnb now) and realize that you’ve left something behind. Of course whatever it may be will be of utmost importance. Often times the hotel or a local drugstore is an obvious and easy stop to pick up what you’re missing. However, for those times where the front desk doesn’t have what you need and the drug store is too far or maybe closed do not panic, there are several options in Chicago that will deliver you want you want – all in less than two hours. All of these places will deliver anywhere within their territory – so even if you’re at a clients office or visiting relatives you can still receive your goods.

Postmates

Our favorite is a delivery service called Postmates. Postmates is changing the way products are delivered city by city. Founded in San Francisco (because that is pretty much where every tech company comes from) in 2011 Postmates connects customers (you) with local couriers to deliver your products.

There are plenty of companies out there (Grubhub, Yelp24 to name a couple) that will deliver you food from a restaurant. What we love about Postmates is their ability to deliver just about anything, including a nice selection of personal care, health and beauty from their “general store” – and typically in less than an hour for a $4.99-$5.99 delivery fee. They also allow you to customize an order. By doing this you really can get a bit more out of Postmates than you could other delivery services. Select a store and tell the courier, in free form, what exactly it is that you want.

A few nights ago we selected our local Walgreens and wrote the courier, “Please pick out the most awesome ice creams that you can and keep the total under $15. We do not care about the brand, the size or the flavor – so long as it is awesome. Thanks!”  Less than 45 minutes later the courier showed up at our door with 5 little pints, their selection was awesome. Mint Chocolate Chip, Moose Tracks, Snickers, Twix and Cookie Dough. We were very impressed.

Amazon Prime Now

if you’re an Amazon Prime member visiting Chicago then you are in luck. Amazon offers their FREE 2hr delivery services on “10s of thousands” of products through their Amazon Prime Now program. If you don’t know what Amazon Prime is you can learn more and receive a 30-day free trail and take advantage of Prime Now.

What we love about Amazon is their unique selection of products, incredible pricing and ease of use. Traveling with a pet – or I guess did you acquire a pet while traveling? No problem, there are over 250 pet products in their assortment right now. Popular categories include personal care, books, games, electronics, fitness, baby, beauty & they also ship from a handful of local retailers too.

There are a couple of aspects to Amazon Prime Now that we don’t like all that much. One is it’s only available on your smartphone. The app works great, but shopping on the computer is much easier than on your cell phone. You also have to be an Amazon Prime member (which costs $99 annually) – where as the other services are a pay per order model.

Google Shopping Express

Free Chicago Walking Tours

Another player in this space that you have heard of before is Google. Google Shopping Express might be our favorite for the sheer variety of stores they deliver from. Costco, check. Walgreens, check. Staples, Toys R Us, Ulta – – the list goes on. We’re also big fans of the fact that you can add your loyalty cards to the order and get credit for any sales or bonus points (unlike many of the other delivery services).

Google Shopping Express allows you to pick delivery times for your products, including next day delivery if you’re outside of their same-day zones. The minimum per-store order is $15 and delivery starts at $5.99/order but they’re constantly running promotions for free delivery and offer a month-long membership for $10/month.

Instacart

Free Chicago Walking Tours

Lastly the app that we feel probably started it all and might be the most well know – Instacart. These folks made a name for themselves delivering whatever you can find in a grocery store but have recently expanded the stores they deliver from to include Target and Petco.

We love their variety of local Chicago grocery stores including our famous meca-of-booze Binny’s Beverage Depot. They also disclose whether or not the prices they charge on a per item basis are the same or higher (and how much higher) than what you would find in the store. For instance you can order from Whole Foods and the prices are the same as in their stores, but if you order from Costco you will pay slightly more. But we love that their upfront with that. Their search is also incredible.

If you’re in a big rush they will expedite your order (for an additional fee) to deliver within an hour.

Did we miss an app or delivery service doing an awesome job in Chicago? Let us know!

Your guide to getting around in Chicago

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Chicago is the countries 3rd largest city (as of July 2014) which means that you have access to all the bells and whistles as it pertains to getting around. Bikes, cars, buses, trains, boats – all are available to help you get from point A to point B in Chicago. But all of these options can be confusing. We’re here to help you sort them out.

Chicago Public Transportion

Besides walking – which we we talk about a little later – using public transportation in the City of Chicago is the most economical way of getting around. And with hundreds of bus routes, high-speed rail and our famous “L” trains it’s convenient too. Chicago is home to the country’s second largest public transportation network (more than 1.7 million rides per day). This system is operated, managed and serviced by the Chicago Transit Authority.

bus

Here is a quick breakdown of your options provided by the Chicago Transit Authority (CTA):

  • Buses – CTA operates 1,865 buses, 128 routes and 1,354 route miles.* The bus routes are all numeric (i.e. route 36 or route 151). Our favorite app to help you manage arrival times of buses at specific stations are Ridescout & Ventra. Speaking of Ventra, make sure you read this section below on what exactly Ventra is and how to use it.
    • Full bus fare: $2.00
  • “L” Trains – The “L” stands for elevated, as in the trains run above the ground. These trains are often the most efficient to connect commuters to long(ish) distances within the city. The lines are organized by color. Blue, Red, Purple, Pink, Yellow, Green, Orange & Brown. There are trains that run to O’Hare (Blue Line) and Midway (Orange Line). Check out this “L” train map to familiarize yourself with the routes.
    • Full “L” train fare: $2.25
  • Metra – This is Chicago’s high-speed rail that connects the city with the surrounding suburbs. Because of how much ground is covered with these trains,  your best bet to learn which route is for you is to visit the official Metra website or Contact Us with any questions on planning your trip.

Visit CTA Fares & Tickets information.

Now is a great time to talk about Ventra. Ventura is the contact-less payment system used by the CTA. Ventra has an app that allows you to purchase mobile tickets and track arrival/departure times for buses and trains.

Buses will still accept cash (exact change only, $2 per route) but you will have to purchase a Ventra ticket when you ride the “L” trains. There are two options:

  1. Purchase a disposable ticket. The cost is actually $3.00 when you buy a single ticket from the Ventra machine at the train station. This includes your ride, up to 2 transfers and a $.50 limited use media fee. We have no clue what the limited use media fee is.You can also purchase a 1-day pass (still disposable) for $10. This pass is good for unlimited rides on CTA buses and “L” trains for 24hrs. If you think you are going to ride the trains and buses a few times in a day this is a great option.
  2. Purchase a plastic Ventra card and load cash balance or longer-term passes. This will cost you $5 initially when you purchase at the vending machine or a local retailer – the good news is you can covert that $5 into a transit credit by registering your account online at Ventra.com within 90 days. This is a great option if you’re going to be using public transportation for a week or longer.
    • 3-Day Pass – $20
    • 7-Day Pass – $28 ($33 if you include Pace bus service that services the Chicago Suburbs)
    • 30-Day Pass – $100

Chicago by Bike

bikes

Depending on which blog/news outlet you read Chicago can rank anywhere from the #2 most bike-friendly city in America to #6. Either way that is pretty dang good. Currently Chicago has over 200 miles of protected bike lanes in the city, 18.5 miles of off-street bike lanes along Lake Michigan and more than 13,000 bike rack spots. If you’re a cycling enthusiast than we probably won’t tell you much that you don’t already know. But if you’re visiting the city sans bike and are interested in riding, then make sure you check out Divvy.

Divvy Bikes is Chicago’s bike-sharing program with 4,760 bikes spread across their 476 stations throughout Chicago. Divvy bikes are available 24 hours a day, 365 days a year.  You will want to read the how-to-guide provided by Divvy for all of the important details, but the basics are this:

  • You either purchase an annual membership online or, most likely, you will purchase a 24hr pass at the Divvy bike station near you. $9.95 for 24hr pass, $75 for annual pass.
  • 24hr pass purchases receive a code they enter into the bike station that allows them to use the Divvy bike for 30 minutes. Riders need to return the bike to any Divvy station within 30 minutes. You will be charged ($2 – $8) for any overtime. See Divvy pricing schedule for more details.
  • Rinse and repeat – you can do this for up to 24hrs with the $9.95 pass. It’s unlimited.

Tip: You could theoretically return and re-rent your Divvy bike immediately for those trips that are longer than 30 minutes. But if you’re going to ride for miles and do not want to stop, you’re better off renting a bicycle for the day from a bike shop. Bikechicago.com (Bike & Roll) is a top-rated bicycle renting and tour company in Chicago. $9/hr, $30/half day and $36/full day.

Chicago By Car

uber

There are plenty of options for getting around by cars in Chicago – you can drive (if you’re brave or have to), you can hail a taxi (easy breazy) or grab an Uber or Lyft (our personal favorite).

Taxis
If you’ve taken a taxi before then you are in good shape. There aren’t really any curve balls that will be thrown at you unless you take a city-based taxi from O’Hare airport and they drive you to a suburb – then you will be charged time and half. Please find below the rate schedule for taxis in Chicago as of January 1, 2016.

  • $3.25 base fare
  • $2.25 each additional mile
  • $.20 for every 36 seconds time elapsed
  • $1.00 first additional passenger
  • $.50 each additional passenger after the first additional passenger
  • $50.00 vomit cleanup fee
  • $4.00 Illinois airport departure tax

Private Transportation
Technology companies such as Uber & Lyft are taking the country by storm offering customers the ability to quickly schedule a car to pick them up and take them to their destination within minutes from their smartphones – and most of the time it’s cheaper than a cab.  Our two favorites are Uber & Lyft.

Both Uber & Lyft work in the same way. You download the app, setup an account, add your credit card information and start booking your rides. It really is so easy. Once you try out one of the companies it will be hard to go back to the traditional hailing a cab – especially in bad weather. Some other aspects of this type of ride that we love is not having to exchange cash or even get your wallet out. The transaction is all handled through the app with the credit card information you provided and saved to your profile. The drivers are rated by users (on a scale from 1-5). If drivers are poorly rated they risk having their driving privileges suspended (i.e. – can no longer make money). Drivers are therefore have an incentive to provide great service and get great reviews.

If you haven’t tried Uber or Lyft we have a special new customer promotion for you. You can get your first Uber ride for free (up to $15) and you can get $50 in Lyft ride credits (5 separate $10 credits) by signing up and using their apps today. New customers only.

Driving & Parking
We’re not sure where to start with this one. Driving in any city, including Chicago, can be a pain in the butt. Traffic into and out of the city, especially in the rush hour morning and evening, can drive just about anyone crazy. If you have (or want) to drive we recommend downloading either Google Maps or Waze. These two transit apps will ensure that your drive will be as fast as it possibly can be.

Parking is an entirely separate can of worms. So you made it to downtown Chicago and you still are sane? Great, but now you much find where to park. Chicago is not making it easy on your either. We have free parking on the streets, we have paid parking on the streets and we have permit-only parking on the streets – so make sure you are paying attention!

For those of you that are less adventurous and want to be sure you’re in a proper parking spot we have some good news. Once again technology comes to the rescue with a couple of apps helping you find the closest and cheapest parking available in the city.

  • Parking Panda will help you locate a parking spot by providing an address, city, neighborhood or zip code. They bill themselves as the #1 Parking App.
  • SpotHero operates in the same fashion priding itself on how quickly you can find, secure and pay for parking on their app.

Chicago by Boat

That’s right, boats. Chicago Water Taxi operates between a few popular locations along the famous Chicago River in the heart of downtown Chicago. Chicago Water Taxi Day Passes ($8 on weekdays, $10 on weekend), 10 ride passes ($17.50 weekday, $30 weekend) and a monthly pass for $60.

*Chicago Transit Authority, Spring 2016

12 sites to help you plan an unforgettable visit to Chicago

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Chicago is a massive city – covering over 237 square miles. There are roughly 2.7 million permanent residents and more than 48 million visitors to the city each year. There are almost 5,000 restaurants to choose from. You could visit a different museum every weekend and still have leftovers, because we have 60 of them – including the #1 Museum in the World. (spoiler: Art Institute of Chicago). There are over 200 theaters & over 225 music venues in Chicago. Getting around in the city can be a breeze or you could feel like it requires an advanced physics degree. Chicago has 28 bus routes & 8 train routes that connect 146 stations. Over 3,000 bikes spread amongst 300 stations are available to rent by the hour to help you tackle one of the countries most bike-friendly cities. And while Chicago ranks #3 by population in America we’re still home to 8,1000 acres of green space, 580 parks and 26 beaches.

Source: City of Chicago

So how the heck are you supposed to figure all of this out on your short weekend trip or heck, even week-long trip to Chicago? Free Chicago Walking Tours is going to help. We present to you the top 12 resources to “hack” your way to an unforgettable Chicago vacation. These websites are a special selection that will make you you make the most of your Chicago trip by having fun, learning & meeting people.

START HERE WITH THESE GENERAL TRAVEL & CHICAGO SITES

TripAdvisor Chicago – Hear us out first. Free Chicago Walking Tours recommends using TripAdvisor Chicago as a way to start the brainstorming process and see what other visitors did in the city.  There is so much information in one place. From things to do, to restaurants, hotels and short-term rentals. Free Chicago Walking Tours even challenges Chicago-area locals to take a look for themselves and find out what is hot in Chicago.

Wikitravel Chicago – Online since 2003, Wikitravel bills itself as the original crowd-sourced travel guide with over 300,000 destinations, including Chicago. There is so much information here. Free Chicago Walking Tours loves this information because it really doesn’t come with an agenda. It’s simply there – use it as you please. It coves topics you really won’t find on other travel sites. Topics such as staying safe within the city and includes a listing of all of foreign consulates located within the city as well as their address and phone numbers. But there really is so much more than this. if you have an hour or so to spare and have never been to or read about Chicago you must visit this page.

Choose Chicago – Yes, we know. Not really a hidden gem or a secret, but this is a catch-all site that is dedicated to Chicago and it didn’t feel right leaving it off. Choose Chicago has a little (OK, a lot) of just about everything. It can be a bit overwhelming because there is so much information, but used correctly and it can be a real asset. Their Chicago Trip Planner is an excellent place to start for those visiting for the first time or the fifth time.

OVER 30% OF VISITORS TO CHICAGO SAY “CULINARY EXPERIENCES” ARE THEIR PRIMARY REASON FOR THE VISIT. THESE SITES WILL MAKE SURE THOSE EXPERIENCES ARE UNIQUE AND MEMORABLE.

Eater Chicago – If you’re looking for the scoop on Chicago dining, drinking, food and nightlife check this site out. If you’re local and haven’t heard of it then you’re going to have some fun for a few hours. If you’re visiting and want to get down to the nitty gritty here are the best features for you:

  • Eater Chicago Essential 38 Restaurants (the answer to: “Can you recommend a restaurant?”
  • Eater Chicago Heat map (hottest Chicago restaurants)
  • We can’t link to this one, because it changes every weekend. But Eater Chicago has a feature every Friday & Saturday they present the best restaurants in Chicago with last minute reservations available from Open Table. Check it out when you’re in need of a place to eat but completely forgot to reserve your spot.

LTH Forum – This is a legit foodie website. It’s not flashy. It’s not sexy. It gets right down to business. The site is the work of Chicago locals who left another “more restrictive” food blog to start their own. Whether you want to meet up with locals to break bread together or you’re interested in getting the scoop on some neighborhood haunts – check this site out.

WEATHER AND TRANSPORTATION ARE TWO VERY UNPREDICTABLE ASPECTS OF CHICAGO LIFE. USE THESE SITES AND APP TO HELP YOU PLAN AND PREPARE FOR ANYTHING.

Spot Hero – For anyone that is going to be driving and parking in Chicago. This is the app for you. It’s almost too good to be true. You plug in where you need to park (an address, landmark, whatever) and the date range. Next thing you know it’s telling you all the spots – both public and private – that you can park at, their location and their price. That is it. Search for the spot, find the spot and pay for it.

RideScout – The all-in-one-whatever-mode-you-want-to-travel transit app has arrived to Chicago. Yay! This app will help you get from point A to point B. Whether you want to take a taxi, a bus, walk, bike, car share, park your care or whatever. All in one simple screen. This is great for those that want to take advantage of every single type of transportation possible in a city (you know who you are) and for those looking to take the most efficient route because they’re running late. Or for those that just want to see how close their friends can guess as to the time difference between taking a bike vs a ride share. Have fun.

Chicago Pedway – Wait, what’s a pedway? It’s a noun -a footway built for pedestrians in an urban area. In Chicago’s case it’s an underground pedway. But why you may ask? To help give you cover for our awful Chicago winters. Many locals don’t even know about it. Now you’re in-the-know. It’s sort of a tangled mess of underground walkways, but we have to admit it’s quite unique and if you have time (or for some reason you’re visiting in the winter) make sure you take a visit.

Dark Sky – Chicago is the Windy City. You have probably heard all of the silly one-liners. “If you don’t like the weather in Chicago, wait 15 minutes.” Chicago has four distinct seasons and then some. Cheers to Dark Sky and the technology behind it that can alert you down to the minute (not kidding) when it will rain or snow in Chicago.

CHICAGO ENTERTAINMENT. ENOUGH SAID.

Free Museum Passes from the Library – Sorry out-of-towners, this one is strictly for locals with a valid ID and Chicago address only. We just couldn’t leave it off our list though, it’s too good. This might even be the last drop in the bucket to motivate you to pack up and move to Chicago.

Just like the link says, if you have a Chicago Public Library card you can “check out” passes to the museum good for up to two adults. The catch? You MUST be accompanied by a child under the age of 18. And yes, the #1 Museum in the World is on the list.

ChicagoPlays – Remember those 200+ theaters that were mentioned in the opening paragraph? ChicagoPlays will make it much easier for you to navigate all that is happening in Chicago. Find a theatre. Find a play. Look by date. Look by what is hot. Buy Tickets. Have fun.

Did we miss a great site that needs to be added on this list? Let us know by adding your comment below.