20 Free Things to do in Chicago

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.

2016 Millennium Park Summer Movie Schedule

Starting in June and running through the end of August you will be able to enjoy 12 different movies for FREE in Millennium Park on their giant 40ft screen. You can sit back and relax from a seat in the Jay Pritzker Pavillon or breakout the blanket and bottle wine (it’s OK to do so!) and chill out on the lawn.

If you plan on bringing kids just double check the movie that is being shown as there are several ‘R’ rated films.

Each movie starts at 6:30pm every Tuesday. Mark your calendars…

Tuesday, June 21 – Ferris Bueller’s Day Off (PG-13)

Tuesday, June 28 – Soul Food (R)

Tuesday, July 5 – A League of Their Own (PG)

Tuesday, July 12 – Thelma & Louise (R)

Tuesday, July 19 (Double Feature!) – Moonstruck (PG) & Silence of the Lambs (R)

Tuesday, July 26 – Kartemquin Films 50th Anniversary Celebration

Tuesday, August 2 – West Side Story (Unrated)

Tuesday, August 9 – Grease (PG-13)

Tuesday, August 16 – Finding Nemo (G)

Tuesday, August 23 – Purple Rain (PG)

Tuesday, August 30 – People’s Choice (Movie goers will vote)

Have fun and we hope to see you out there!

 

Best Chicago Speakeasies

Everyone likes to be in on a secret. It’s an exhilarating feeling – you’re special, knowing something your coworkers, family or friends don’t. It’s even more exciting knowing a city’s secrets, and trust us when we say Chicago has plenty. Our Free Chicago Walking Tours are loaded with them. When most people think of a night out in Chicago they think of well known areas like River North and Gold Coast–perfectly fine choices no doubt, but what they don’t know is that Chicago has some of the best hidden bars in the country. You can find speakeasies in the strangest locations throughout the city. It’s also a great way to explore new neighborhoods in Chicago. Keep reading to see which bars you cannot miss out on while in Chicago!

Violet Hour

1520 N. Damen, Chicago, IL (Wicker Park)

original_TVH_JohnHerndon__CassandraStadnicki

Source: The Violet Hour

Perhaps one of the most famous bars in the city, The Violet Hour may also be one of the classiest. Located in the bumping and trendy Wicker Park neighborhood, The Violet Hour will make you feel like one of Chicago’s elite. The Violet Hour has no door, sign or light. If you’re not careful you will walk right past the door which is typically painted over and a part of a larger mural that covers then entire front of the building. After ten minutes a bouncer will take you into a waiting room– a sign that you’re in. You must adhere to the strict dress code, never order anything that you’d drink at a frat party and refrain from using your phone.

What you need to know: No reservations. No use of cell phones inside. No baseball hats. No reservations, first come first serve. No ‘O’ bombs or jaeger bombs or any kind of bombs. No Budweiser.

What you need to try: Frites and aioli for a snack and wash it down with their version of a Manhattan – appropriately called Brooklyn.

 

Booze Box

823 W Randolph St, Chicago, IL (West Loop)

003_cousindaniel_boozebox__3612-4-1024x681

Source:Sushi Dokku

Many people have heard of the restaurant Sushi Dokku in West Loop. It’s located in the arguably the hottest restaurant “district” in Chicago today. Sushi Dokku has neighbors with names such as Au Cheval, the Girl and the Goat and The Publican. Randolph Street is a gem amongst the restaurant and bar world of Chicago. But we digress. We’re talking about Booze Box here, the bar in the basement of Sushi Dokku that many that have dined there don’t know about. You have to walk 10 yards south to an alley behind Sushi Dokku where you will see a lonely bright red sign– the entrance to Booze Box. The atmosphere and what they are serving is just as unique as their entrance. Japanese street food, cold draft sake and a rotation of DJs spinning next to the guests at the bar all make a visit here worthwhile.

What you need to know: Booze Box is open only on the weekends – Thursday, Friday & Saturday – starting at 6pm.

What you need to try: Chill Gin Mojito

East Room

2354 N Milwaukee Ave, Chicago, IL (Logan Square)

eastroom

Source: Yelp

To be fair– East Room isn’t a speakeasy all the time. They open their doors to the main street when there is a special event or concert, but all other days you can only get in through the back door. The first time we went there it took us 20 minutes to find the place. Your phone will be telling you you’re standing right in front of it but you won’t see a soul near you. Everyone will be across the street at all the other bars lined up pretty in a row. But don’t give up! Just walk to the back alley until you see a strong looking man leaned up to the wall. He is your way into the second floor– a mix of cheap drinks, good music and wooden benches for good conversation.

What you need to know: Cash only! So, you know…bring cash or someone that has cash.

What you need to try: BYO-Vinyl. Yes, Bring Your Own Vinyl, as in records – East Chicago crowd-sources their music on Mondays.

 

3 Dots and a Dash

435 N Clark St, Chicago, IL (River North)

threedots

Source: Facebook

Consider this a new-age speakeasy. A new-age tiki-lounge-inspired speakeasy. This place is far from your traditional prohibition-era underground hush hush place. It’s still more well known than the other bars, but 3 Dots and a Dash is one of the funnest speakeasies in town. It boasts a Polynesian type theme complete with mini umbrellas in the drinks and almost any type of rum you could possibly dream of. You’ll often see large 21st birthday parties, bachelorette parties and groups of bar crawlers. This is a great speakeasy to have a drink at before hitting the clubs in the area.

What you need to know: It’s tricky to find. Walk up Clark St, then head east on Hubbard and go north up the alley. On your left (west) will be a small hanging sign that says “3 Dots and a Dash” – congratulations, you have arrived.

What you need to try: For those in a large group or with plenty of disposable income – or both, you definitely should order the “Treasure Chest” – a $400 cocktail that is served in a actual treasure chest on bamboo shoots carried in by a couple of waiters. Smoke (dry ice) billows out, the drink is lit up and the waiter pops a bottle of Dom Perignon and pours it into the concoction. Everyone at the table gets a giant straw and has at it.

Door No. 3

1572 N Milwaukee Ave, Chicago, IL (Wicker Park)

door3

Source: Facebook

Another speakeasy located in Wicker Park, Door No. 3 puts you in the mood with a secret entrance in the alley behind the Damen Blue Line stop. What makes Door No. 3 special is the live music. The DJs are skilled spinners that know how to keep people dancing and keep the party going. The interior isn’t shabby either with sexy leather furniture and blue lighting perfect for a chill, relaxed date night. It is also a go to destination to kick off a night of bar hopping in Wicker Park.

What you need to know: There is no food served here. They have a small vending machine   in the corner to satisfy your hunger. They aren’t known for any fancy cocktails either. Hipster beers like PBR and Tecate are available as well as your traditional mixed drinks.

 

Room 13

3222 N Sheffield Ave, Chicago, IL (Lakeview/Wrigleyville)

room13

Source: Old Chicago Inn

No questions about this one – Room 13 is definitely a speakeasy. Or maybe it should be a “speak hard” because it’s not easy to get into. Get it? Ha.

Located a half a mile south of Wrigley field like many speakeasies Room 13 is a part of another business: The Old Chicago Inn Bed & Breakfast. This place has all the markings of a speakeasy. Garden unit, check. Classic American cocktails, check. Dress code, check. Oh, and you seriously need to work to get in.

There are 3 options and only 3 options to get into this place:

  1. Stay at the Inn and you will receive an invite
  2. Buy a membership (aka become a member)
  3. Be a guest of a member

Mic drop. That’s it. If you are not fitting into one of those buckets you will not get in.

What you need to know: This place is seriously awesome.

What you need to try: Their cocktail flight. Reserved exclusively for guests of the Inn simply add the “Speakeasy Flight” to your reservation and you will receive a flight of 4 cocktails while the bartender explains the history of each drink. Cost is $55 for two people.

The Office

955 W Fulton Market, Chicago, IL (West Loop)

office

Source: Yelp

Ah yes, The Office. This will be sort of a good news – bad news situation. Let’s start with the bad news. This is another really tough one to get into. The good news? It’s underneath one of our favorite bars in the city which you can get into (if you have a reservation): The Aviary.

The Office is a 14-seat VIP speakeasy located beneath The Aviary. The bar features drinks and food that you will not find on The Aviary’s menu. If you’re a commoner just having drinks and food upstairs you might notice people going in and out of The Office and wonder – how do I get in? Well…you need to be invited. The staff at The Aviary invite guests to The Office. That’s it. Good luck!

What you need to know: If you have made it inside The Office and have to use the bathroom you’ll take a key from the bar, use the “commoners” restroom and get back inside The Office using the key.  And it’s not exactly cheap either. $20+ cocktails, $30+ appetizers, Make sure you bring your wallet!

What you need to try: The level of attention you receive from the staff and bartenders is incredible here. Instead of ordering off the menu tell the bartender your favorite spirit and let them come up with something that will impress. And if you’re in mood the mood for desert order their ice cream sundae. OMG.

If you have the time give all of these spots a try while visiting. And let us know in the comment section how the night went. We look forward to hearing from you!

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

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

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

Great Chicago Date Nights that are NOT Dinner and a Movie

We don’t have anything against dinner and a movie. It’s a tried and true date night. But when there is so much more that you could do in a place like Chicago why settle? Whether this is your first trip to Chicago and you’re scoping out the Tinder scene or you have been married for 30 years these date ideas will help you step out of the box and create an unforgettable day.

Second City Chicago

One of our favorites. If you like to laugh – and you think that your partner will too – then this is for you. There are all different kinds of shows at Second City. From improv to standup to productions You will want to check their calendar and book your tickets in advance, especially if you plan on taking in a show on the weekends as this place will sell out.

Bar:  Good news the venue is located in the heart of Old Town that has no shortage of options to grab a before or after show drink(s). We recommend checking out the Old Town  Pour House with one of Chicago’s largest beer selections only a 5 minute walk from the stage.

Adler Planetarium

planetarium

We love this because it will give both of you the chance to walk around (which encourages conversation) and the sights themselves will be the topics of those aforementioned conversations. Plus you will get a chance to lay out on your backs and watch the stars. All this for $12 with their general admission, not bad at all. (Tickets can be much more expensive once you start tacking on shows and what not)

Bar: The Adler Planetarium is located on Chicago’s Museum Campus with it’s neighbors the Shedd Aquarium and Chicago Field Museum. The point we’re trying to make is there aren’t many good bar options within walking distance. If you are a rockstar and plan your date accordingly you could attend Adler After Dark and have your cocktails there. For those of us not as skilled in the craft of extreme planning pop into the Palmer House and visit their Lobby Bar at one of Chicago’s most famous hotels.

Kayaking

It’s probably not the activity that comes to mind when someone says “Chicago” – but when it’s summertime here in the Windy City taking an architectural kayaking tour along the Chicago River will be tough to beat. There are a handful of different tour companies operating in Chicago with slightly different itineraries. You can even rent kayaks and give your date a special one-on-one tour. And if kayaking isn’t quite your thing you can always opt for stand up paddle boards.

Bar: This one is a little tricky since you might be entering or exiting the river at different points. We certainly don’t recommend you pound drinks before getting in a kayak -so please, save these for after. One of our favorite spots that will give you views of the river, skyline and Lake Michigan is the Terrace at Trump Tower. Just be ready, this isn’t the cheapest spot – cocktails will set you back $20+ per. YOLO.

Adult Arcade

If you haven’t heard of these beer-serving, 21-and-older-to-enter, throwback arcades that are popping up in cities across America well then you are welcome. A favorite of ours also happens to be in our of our favorite neighborhoods of all time. Emporium Arcade Bar in Wicker Park.  TMNT – check. NBA Jam – check. Live music – check, although – check their schedule because it’s not every night.  And even better news too – most of the music events are FREE.

Bar: Hmmm. How do we handle this one? Technically Emporium Arcade Bar IS A BAR. If you think that you might need a bit of liquid courage before taking your date on in Mortal Kombat then you’re in luck. Up and down Milwaukee Avenue, Division and North Avenue are dozens and dozens of bars. Good luck making it into the arcade and not just bar hopping in this part of town.

Lincoln Park Zoo and/or Conservatory

Lincoln_park_conservatory

We sort of have you covered both summer and winter with this one. If you come in the summer, great – take a stroll through the park, the zoo and the conservatory. We call that the Trifecta. Here in the colder months? That’s OK too – a stroll through the conservatory is even more impressive this time of the year. Especially if you catch their seasonal decor before it’s taken down the first week of January.  Regardless there will not be a shortage of things to look at and do. You will be impressed with how quickly you escape the hustle and bustle of the city here.

Bar: So many great options here. The Barrelhouse Flat gets high marks for their unique cocktails and romantic setting. You can’t get more cozy than Chicago Pizza & Oven Grinder Company (good luck getting a seat though). And for those interested in a really late night cocktail Ravens is open until 4am on most nights.

Now that you know what date nights we like, what was your best date in Chicago?

Best Free Chicago Year-Round Things to Do

We operate a Free Chicago Walking Tours so it is only fitting that we present the best free things do to in the city of Chicago. And we live here, so we have a good idea. There are a lot of free things to do in Chicago – but not all of them are good for the winter. No beaches, outdoor concerts or farmers markets in January. Those have their place, just not on this all year, four seasons list of free things to do in Chicago.

1. Visit a brewery

brewery

Visiting a local brewery is a great way to get out of the cold and experience something that is truly unique to Chicago. We have no shortage of options in Chicago. Not all of them are free though. If you’re looking for the most economical tour of a brewery in the city you have two great options. Revolution Brewing located on Kedzie just north of Belmont. Your other option is Lagunitas and their huge tap room in Chicago’s Douglas Park neighborhood. Both offer great free tours and tasty brews.

2. Chicago Cultural Center

chicago cultural center

Located in the heart of Chicago near the Northwest corner of Millennium Park the 100+ year old gorgeous building has a storied past and was converted to it’s current use in 1991. Here you will find tons of free things to do from concerts to theatre to exhibitions from artists. The Chicago Cultural Center tends to fly under the radar – so both locals and tourists should seek this out.

3. Lincoln Park Conservatory

Lincoln_park_conservatory

Just about everyone is aware of Lincoln Park – both the actual park and the neighborhood. The Lincoln Park Zoo is an incredible free attraction best suited for warmer weather. (Although they do have a great winter light festival too). What you might not know is that the Lincoln Park Conservatory is a great safe haven in the colder months. Operated by the Chicago Park District, this free attraction has greenhouses and gardens under it’s roof. Seasonal displays make sure that whenever you go there will be something different. Stepping into this building after being in the hustle and bustle of the city streets is really incredible.

4. Navy Pier

navypier

Navy Pier advertises itself as a landmark – and well, we have to agree. Sure the summer time is probably the best time to visit (for just about anything in Chicago) but don’t let that stop you from visiting during the snowy months. Navy Pier is non-stop. There is no charge to get into and walk through Navy Pier, but some of their events will cost money. Make sure you check their calendar and sign up for their newsletter to keep up to date with all that is going on at Navy Pier.

5. Harold Washington Library

library

This very well could be #1. The library has an entire section of it’s website dedicated to planning a visit and their own top 10 things to do while there. Read a book, attend a wedding or visit their winter garden. Who would have thought that would all be under the same library roof?  Every single day there is something going on here. When we wrote this post there is a toddler story time and a how to make a small chair with a laser…so, who really knows what they will be up to when you visit. Check out the Harold Washington Library website before you go.

6. Chicago Botanic Gardens

botanicalgarden

Some would say that this botanical garden is even BETTER than a visit to the Lincoln Park conservatory but it’s a 17.5 mile drive outside the city in Glencoe. That being said it’s crazy to think that the incredible Chicago Botanic Garden is free admission (not pets allowed though). If you drive you might have sticker shock at the $25 per car parking charge but you will not be disappointed. For those bold enough to jump on our Metra trains you can hop on that and walk from the Braeside station to the gardens.

7. Eataly

etaly

A grocery store is on the top free things to do in Chicago? Well, yes – sort of. It’s part grocery store, part sit-down restaurant, part bar and part workshops and spectacles. There are only two locations in the U.S.  – Chicago and New York. Pop in for sandwich, some specialty meats, to visit their Nutella bar, a glass of champagne or their award-winning cheese shop. Located just east of Michigan Avenue on Ohio Street the location is ideal for anyone visiting Chicago.

8. Chicago Pedway

pedway

Or as it is technically known: Downtown Pedestrian Walkway System. This under and above ground (all enclosed) walkway connects more than 40 blocks of downtown Chicago real-estate with more than 5 miles of weather-safe paths. Private buildings, public builds and CTA transit are all connected. Look for the special Pedway symbol (shown above) to know that you have found an entrance to the walkways.

Did we leave something off the list? Help us make it right by letting us know in the comments below.

12 sites to help you plan an unforgettable visit to Chicago

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.