Chicago is one of the most beautiful and exciting cities in the United States and is well worth a visit for any travel enthusiast. That being said, it’s also quite a large and expensive city, almost overwhelmingly so. If you’re a budget traveler looking to save money without sacrificing an unforgettable traveling experience, it can be difficult to know where to stay, what to eat, and what to do during your trip to Chicago. Don’t worry, our Ultimate Chicago Budget Travel Guide will show you the ins and outs of the best that Chicago has to offer.
Accommodation: Where to Stay in Chicago on a Budget
When it comes to accommodation, you have several options: hotels, hostels, and rentals/Airbnb. Each of these types of housing has its own pros and cons, including cost, privacy, amenities, and location. That being said, Chicago is home to a wide variety of each kind of accommodation, so no matter which option best suits your personal needs, you’re sure to find a quality hotel, hostel, rental, or Airbnb for you to call home during your stay!
Hotels
Obviously, hotels are the most traditional type of travel lodging, and they’re a great choice for you if you value things like privacy and amenities most highly when looking for a place to stay. Unfortunately, Chicago has some of the highest hotel room rates out of any major city in the United States. The average Chicago hotel room will cost you about $130 a night. However, the highest-rated and most luxurious hotels in the Loop will likely charge anywhere between $250 and $500 a night. If you’ve got your heart set on staying in a top-rated hotel during your stay in Chicago, you’re going to need to book your room in advance to get the best rates.
Here are a few of our favorites that offer a perfect balance of location, amenities, and price per night.
The ACME Hotel Chicago is a boutique hotel in River North, only 2.5 blocks away from the main downtown area. It’s quite youthful and high-tech, with Amazon Alexa devices in each room, a fully-stocked minibar that automatically adds anything you take to your tab, and Apple watches available to check out from the front desk. One bedroom for two people at the ACME Hotel will cost you a little over $100 a night.
The Millennium Knickerbocker Hotel Chicago is a historic location originally opened in 1927. It’s only one block away from Michigan Avenue, meaning that it occupies a prime location for any Chicago tourist. The hotel offers free weekly history tours, which are great if you’re interested in hearing more about the hotel’s connections to infamous figures like Al Capone and Hugh Hefner. You can expect to pay between $90 and $150 a night for one bedroom at the Millennium Knickerbocker, making it much less expensive than other Chicago hotels.
The Hilton Garden Inn Chicago Downtown/Magnificent Mile definitely boasts a wide variety of amenities, including free Wi-Fi, Keurig coffee machines in each room, and an indoor lap pool and hot tub. It’s only two blocks away from Michigan Avenue and a fifteen-minute walk from Millennium Park. It’s a part of the Hilton Garden Inn chain, so it doesn’t have the same personal, unique feel as more historic, local hotels, but it makes up for its generic qualities in amenities and location. One bedroom for two people at the Hilton Garden Inn Chicago Downtown/Magnificent Mile will run you a little over $100 a night.
Hostels
When you think of the word “hostel,” you might think of overcrowded, uncomfortable lodgings that offer almost nothing in the way of privacy. Actually, hostels are quite underrated and might be a great option for you if you’re looking for a more social traveling experience. Especially if you’re traveling alone, staying in a hostel is an excellent way to meet new people from all corners of the globe and even make some new friends!
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If you’re interested in hostels but would prefer not to sleep in a dorm-style setting, you’re in luck! Although traditional hostels are designed with common sleeping areas, many Chicago hostels also offer private rooms for a slight upcharge. Hostels are far more cost-effective than hotels in Chicago. A bed in a dorm-style room will run you approximately $18-50 a night, and a private room will likely cost between $60-100 a night.
The Freehand defines itself as part-hotel and part-hostel. Located in the trendy River North neighborhood, the Freehand offers a wide variety of amenities, including complimentary Wi-Fi, a fitness center, a guest kitchen and lounge, daily housekeeping, and an in-house cocktail bar called the Broken Shaker. Spots in a shared coed room start at $50 a night, while private rooms start at $150 a night.
The HI Chicago is the largest hostel in the city, located smack dab in the middle of the Loop. It boasts a selection of curated free tours and activities, complimentary Wi-Fi, free continental breakfast every morning, and a room full of pool and ping-pong tables so you can relax, unwind, and meet some new people over a game! Spots in dorm rooms start at $34 a night, and private rooms start at $119 a night.
Found Chicago is also located in River North, within walking distance of the major downtown area and Michigan Avenue. It features free Wi-Fi, exclusive concierge service, and an in-house coffee shop, restaurant, and karaoke lounge called the Blind Dragon. They offer both coed and single-gender dorms, which start at around $30 a night, although the coed dorms will probably be a few dollars cheaper. Their private rooms will run you a little over $100 a night.
Rentals/Airbnb
Rentals and Airbnbs are a great way to live in a real Chicago neighborhood, like a local. Obviously, they provide a homier and more organic experience than a hotel or hostel would. Depending on the location and luxuriousness of the room in question, an Airbnb in Chicago will cost you anywhere between $100 and $350 a night, which is cheaper than the average hotel, but more expensive than the average hostel. The closer your apartment is to major tourist attractions like Millennium Park or Navy Pier, the more expensive it’ll likely be. Renting a more cost-effective room doesn’t necessarily mean that you’ll end up in a poorly-furnished dump of an apartment, but it might mean that the neighborhood you stay in is further away from the downtown area and all of its tourist attractions.
Transportation: How to Get Around
Chicago is a pretty large city, which means getting from neighborhood to neighborhood can be difficult, if not impossible on foot. Even when you stay within one neighborhood, Chicago is still not a particularly walkable city. You technically could take cabs everywhere, but that transportation strategy would quickly add up. Fortunately, Chicago has a wide variety of transportation options that make getting around from place to place much easier and more affordable.
Ridesharing
Ridesharing has quickly become one of the fastest-growing and most popular transportation options over the past couple of years. If you already regularly use ridesharing apps at home, you’re in luck, because Chicago has the lowest UberX rates out of any major city in America. Even if you don’t make a habit of Ubering from place to place in your hometown, you may find that the rates in Chicago make ridesharing here much more affordable.
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In order to compete with Uber, Lyft rates in Chicago are also quite low. If your personal Lyft rider score is high, you may also be able to take advantage of 10% discounts and coupon codes that cut the cost of ridesharing even further. No matter which rideshare app you prefer, you’ll find that it’s quick, easy, and inexpensive to use Uber or Lyft in Chicago.
Public Transportation
Chicago also has a fairly extensive and efficient public transportation system, which consists of buses and “The El,” Chicago’s version of a subway that runs aboveground on elevated tracks. The El is actually the second-busiest city railway system in the United States, with New York City’s subway system being the first. It runs twenty-four hours a day, seven days a week and features eight different lines, categorized by color, that will get you practically anywhere in Chicago you need to go.
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In order to pay, you’re going to need to buy a Ventra ticket from a designated Ventra vending machine, available at all train stops. You can buy a single-use ticket, which is good for up to three rides within two hours of your first swipe. You can also buy one-day, three-day, seven-day, and thirty-day tickets, which will allow you to ride the train an unlimited number of times within the given time period. Finally, if you’re planning on staying in Chicago for a longer time, you can buy a Ventra card and download the free Ventra app, which allows you to create a reloadable public transportation balance.
CTA Buses: The bus system is also very efficient and comprehensive, with most buses running from very early in the morning to very late at night. Regular bus fare is $2.25 (as of 10/1/2018). Unlike on the El, you can use cash to pay your bus fare, or you can use your Ventra card or ticket to pay. If you’re trying to plan a trip or just wondering where the nearest buses are, you can use your smartphone to visit the Chicago Transit Authority (CTA) bus tracker, which uses GPS technology to track the location of all CTA buses in real time, and reports their estimated arrival times, approximate location on a map, and notifies you of any major delays.
Finally, the Metra is the train system that moves people in and out of the city from the neighboring suburbs. If you’re planning on leaving the major metropolitan area to check out the rest of Chicagoland, the Metra is the perfect mode of transportation for you. There are eleven Metra routes in total, with two major train stations in Chicago that serve as their hubs: Union Station and Ogilvie Transportation Center. Like the other forms of public transportation in Chicago, you can use the Ventra app to buy Metra tickets or visit a ticket counter at the train station.
Depending on the distance of your destination suburb from Union Station or Ogilvie Transportation Center, a one-way ticket will cost you anywhere between $4 and $9.50. However, there is a $5 surcharge if you buy your ticket from the conductor once you’ve already boarded the train. On Saturdays and Sundays, you can buy an unlimited weekend pass for $10. Because so many suburb-dwellers use the Metra to commute to and from work, you can expect the trains to be more heavily populated before 8:00 am and after 5:00 pm on weekdays, as well as on popular holidays and events such as Lollapalooza, St. Patrick’s Day, the Chicago Pride Parade, and the 4thof July.
Bike Sharing
Chicago also boasts an urban bike-sharing program called Divvy. If you’re looking to get a good workout as you travel from destination to destination within the city of Chicago, Divvy is the perfect transportation option for you. All you need to do is download the free app on your smartphone, select a price plan, and find one of the 580 Divvy bike stations located around the city. When you’re done for the day, just drop your bike off at another Divvy bike station! The majority of Chicago’s Divvy stations are located downtown in the Loop, so this method of transportation is best for those who are planning to stay within the main metropolitan area of Chicago for the day.
Driving
If you’re planning on driving your own car or a rental vehicle during your stay in Chicago, we highly recommend that you download a parking app like Spothero or ParkWhiz. Although driving your own vehicle is probably one of the easiest and most convenient ways to get around the city, parking spots in Chicago can get pretty expensive, especially in major tourist areas like Michigan Avenue and Wrigleyville. The average parking rate per day in Chicago is $34, and even then, this rate assumes that you’re leaving your car parked in the same spot all day long. Spothero and Parkwhiz will help you find a great parking spot that doesn’t charge such exorbitant rates.
Food: A Guide to Chicago’s Delicious and Inexpensive Food Scene
Chicago is a foodie’s paradise, with an incredible variety of restaurants that serve virtually any type of cuisine at any price point. Whether you’re looking for a hot slice of pizza, a refreshing bubble tea, or a hip new brunch spot, Chicago has you covered! No matter what neighborhood you’re in, you’re sure to find a host of amazing restaurants.
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The Loop
The Loop is the central business district in downtown Chicago, which means it’s got the requisite Starbucks and McDonald’s locations that characterize any modern metropolitan hub. However, it also has some amazing, unique restaurants that can only be found in Chicago.
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For example, if you were to pass Cafecitoas you walked down the street, you might be tempted to write it off for its small size. On the contrary, this deceptively small restaurant serves what many consider to be the best Cuban sandwiches in Chicago. Their service is quick and friendly without sacrificing food quality, making it a lunchtime favorite for many business professionals that work in the Loop. We also recommend you try a cup of cafecito, the restaurant’s namesake. It’s a super strong, sweet shot of Cuban espresso that will jolt you awake if you’re tired from a long day of walking around.
Wildberry Café is a favorite breakfast and brunch spot for many Chicago locals. It serves a variety of pancakes, crepes, waffles, and French toast, including flavors like blackberry key lime pie, red velvet, and caramel apple pecan. There are two Wildberry Café locations in the Loop: one at the Prudential Tower and one at the Water Tower Place, so you can choose to visit whichever location is closest to you!
Wicker Park and Bucktown
Wicker Park and Bucktown are two of Chicago’s hippest, trendiest neighborhoods. In addition to housing some of the coolest thrift stores and boutiques in the city, Wicker Park and Bucktown are also home to many amazing restaurants serving innovative and delicious food.
OUR FAVORITE WICKER PARK FOOD TOUR
Mindy’s Hot Chocolate is obviously most well-known for its decadent hot cocoa, which comes in unique flavors like lemon vanilla, Mexican hot chocolate, and of course, old-fashioned milk chocolate. They also feature a brunch menu that rotates seasonally. Depending on what month of the year you’re planning to visit Chicago, you might find yourself devouring brioche French toast, pork belly stir-fry, or even a cured salmon bagel sandwich.
Big Star Tacos is also a Wicker Park favorite, serving delicious dishes inspired by authentic Mexican street food. They offer a wide variety of tacos, including al pastor, carne asada, and chorizo, as well as vegetarian options that come filled with tofu, potatoes, or carrots. They also have a location in Wrigleyville, so you can swing by for some post-baseball game dinner.
The West Loop
The West Loop is another one of Chicago’s hippest neighborhoods. In recent years, the area has undergone rapid change and is now home to some of Chicago’s newest, trendiest, and most popular restaurants.
Au Cheval has quickly become one of the most coveted restaurants in the entire city. Lines for a table often stretch out the door and down the sidewalk. Their classic cheeseburger, which is served from morning until night, is considered by many to be one of Chicago’s best. If you’re not a burger fan, you can order their honey-fried chicken, chopped salad, or chilaquiles. Au Cheval famously does not accept reservations, so you’d best get there early unless you don’t mind waiting outside for over an hour.
The Little Goat Diner is an offshoot of acclaimed chef Stephanie Izard’s main restaurant, the Little Goat. It serves inventive re-imaginings of classic diner foods, like pork belly pancakes and guanciale grilled cheese, and is open from early in the morning until late at night. Meals at Izard’s main location, the Little Goat, are quite expensive and generally require reservations made far in advance, but if you’ve got your heart set on trying Stephanie Izard’s food during your time in Chicago, the Little Goat Diner is much more accessible and might be your best bet!
Chinatown
Chicago is home to the second-oldest Chinatown in the United States. It’s split into two sections: Old Chinatown and Chinatown Square. Each section is full of great restaurants that serve regional food from different provinces and cities in China, as well as Asian grocery stores, bubble tea vendors, bakeries, candy stores, and more.
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Joy Yee Noodle is a relatively new establishment to Chinatown, but it has quickly become renowned for its dizzying variety of bubble tea flavors. There are over 150 flavors to choose from, including classic flavors like Thai iced tea and taro, but also more adventurous flavors like durian and rose. Joy Yee also serves delicious variations on noodle soups and fried rice, so you can enjoy a meal there before ordering your bubble tea.
Bubble tea from Joy Yee Noodles
MingHin Cuisine in Chinatown Square is a local favorite for dim sum. If you’re going to be in Chicago over a weekend, we recommend stopping by MingHin Cuisine on a Sunday morning to enjoy dim sum classics like steamed pork buns, egg custard tarts, and fried taro puffs.
Attractions: What to Do in Chicago
Chicago is a big city with a practically infinite number of attractions and activities. From the moment you wake up to the moment you go to sleep, you’re sure to find a fun, exciting way to entertain yourself. Whether you’re interested in museums, sports, spending time outdoors, enjoying a live performance, or even partying in a bar or nightclub, Chicago has a multitude of options that’ll cater to your exact needs!
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Museums
Chicago is home to some of the best, most interesting museums in the entire country. Whether you’re interested in art, science, or history, Chicago has a museum for you. If you plan on visiting more than 1 museum during your stay you need to check out and purchase a Chicago Savings Pass.
The Art Institute of Chicago is one of the best, most lauded art museums in the United States. It’s particularly well-known for its collection of Impressionist and post-Impressionist art and is home to some world-famous paintings including Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, Grant Wood’s American Gothic, and Edward Hopper’s Nighthawks. Its newly-constructed Modern Wing has a dazzling collection of modern and contemporary paintings, sculptures, and photographs. It also features a bridge that leads directly to Millennium Park.
The Field Museum is part of Chicago’s Museum Campus, located on the southernmost end of Grant Park, along with the Adler Planetarium, the Shedd Aquarium, and Soldier Field. The Field Museum is one of the largest natural history museums in the world. It’s especially famous for housing the most complete T-rex fossil in the world, lovingly nicknamed “Sue” after the lead paleontologist who discovered it. It also features incredible exhibits on archaeology, anthropology, and biology.
The Museum of Science and Industry is one of Chicago’s most unique museums. It’s located in the Hyde Park neighborhood and features an incredible variety of interactive, innovative science-themed exhibits, with topics ranging from extreme weather to genetics to agriculture. It’s an amazing place to spend the day for families with children of any age.
The Museum of Contemporary Art Chicago is one of the city’s smaller and more underrated museums. Throughout its history, it has hosted exhibitions for some incredibly talented contemporary artists, including Frida Kahlo, Jeff Koons, and Takashi Murakami. It frequently rotates the art pieces on display, so you’re sure to discover some new, exciting, and thought-provoking art no matter when you decide to make a visit. It also features a pay-what-you-can admissions program, making it significantly more cost-effective than many of the other museums in Chicago.
Finally, the Chicago Cultural Center is another great place to discover some exciting art and architecture. It’s famous for housing the world’s largest Tiffany stained glass dome, as well as some incredible interior architecture, including ceiling mosaics and carved marble. It also hosts free, rotating art exhibits by local artists.
Most recently, the Cultural Center displayed a never-before-seen segment of a mural painted in collaboration between iconic contemporary artist Keith Haring and the students of Chicago’s public school system in 1989.
Parks
Although Chicago is well-known for its brutally cold and snowy winters, it’s incomparably beautiful in the spring and summertime. If you’re looking to get some fresh air and stretch your legs, be sure to visit its beautiful parks.
Perhaps the most famous park in Chicago is Millennium Park, home to Anish Kapoor’s stainless-steel sculpture Cloud Gate, more commonly known as “The Bean.” It is the most popular photo ops in the entire city – and tops in the midwest actually. You can also visit Crown Fountain, an interactive public art installation and fountain that features 50-foot LED sculptures that look like huge faces spitting streams of water.
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On summer evenings, Chicago frequently hosts free events at Jay Pritzker Pavilion, including movie nights and jazz concerts.
Grant Park is often affectionately referred to as “Chicago’s Front Yard.” Stretching an impressive 319 acres, Grant Park encompasses a number of beautiful fountains, gardens, skate parks, dog parks, and sculptures. If you’re into jogging, biking, or just taking long, leisurely strolls, you can walk up and down the Chicago Lakefront Trail, which offers a picturesque view of Lake Michigan.
Every year in August, Grant Park is also home to Chicago’s biggest and most popular outdoor music festival, Lollapalooza, which lasts for four days and features big-name headliners like Bruno Mars, The Killers, Lana del Rey, and the Red Hot Chili Peppers. If you want to attend Lollapalooza, make sure you’re ready to buy your tickets the instant they go on sale, because passes usually completely sell out within 24 hours.
The Chicago Riverwalk is a newly-completed attraction. Although it’s technically not a park, it still offers a great opportunity for you to sightsee while enjoying the beauty of the great outdoors. We love the Riverwalk so much we have dedicated an entire tour to this beautiful stretch along the Chicago River. It stretches a little over a mile along the Chicago River. There are bars, ice cream parlors, and coffee shops scattered all along the way, so if you’re ever tired of walking, you can stop for a drink or a snack. There are also designated outdoor seating areas that allow you to rest comfortably along the river and people-watch.
Sports
Chicago has its own hockey, basketball, soccer, and football teams, as well as two baseball teams. No matter what season you visit in, there’s sure to be a game going on nearby. Wrigley Field is one of Chicago’s most famous tourist attractions, and for good reason. It’s home to the Chicago Cubs, one of the city’s two Major League Baseball teams. It’s located in the Wrigleyville neighborhood, which is obviously named after the stadium itself. Wrigley Field is also the second-oldest professional baseball stadium in the United States, with picturesque ivy-covered walls and one of the only remaining hand-operated scoreboards in the Major Leagues. When visiting Wrigley Field, you can choose to catch a Cubs game, or you can take a tour of the stadium itself. Tickets are available for purchase online at Wrigley Field’s website.
Soldier Field, located in the Museum Campus, primarily serves as home to the Bears, Chicago’s professional football team. However, during the off-season, it also serves as a venue for some of the most famous musicians in the world during their international tours, including Beyoncé, Taylor Swift, and the Rolling Stones. When there isn’t a football game or concert happening, Soldier Field is still in use as a hockey rink, soccer field, and rugby pitch.
The United Center is home to the Blackhawks, Chicago’s hockey team, and the Bulls, Chicago’s basketball team. Like Soldier Field, the United Center also frequently serves as a venue for big-name concerts, having hosted artists like Kanye West, Bon Jovi, Barba Streisand, Fleetwood Mac, and Jay-Z. No matter whether you visit Chicago in the summer, winter, spring, or fall, the United Center will undoubtedly be hosting an exciting event, whether it be a sports game or a concert.
Shopping
If you love to shop, Chicago is an excellent place for you to indulge in some retail therapy. Many well-known and luxurious fashion houses, like Louis Vuitton, Chanel, Burberry, and Gucci, have locations on Michigan Avenue. Otherwise known as the Magnificent Mile, this long stretch of retail locations is probably the premier spot for window shopping in the entire city. If designer clothes and handbags are a little out of your price range, you can also find stores like Uniqlo, Topshop, Zara, and Forever 21 along the Magnificent Mile. The Water Tower Place, a vertical skyscraper mall located on Michigan Avenue, houses over 100 different stores, from Adidas and Aritzia to Sephora and Swarovski. It also has an American Girl Place and a kiosk on the first floor that serves scoops of raw, edible cookie dough, making it a great place to go if you’re traveling with kids.
If thrift shopping is more your speed, be sure to visit Wicker Park during your time in Chicago. This trendy neighborhood is home to some of the best thrift shops and vintage stores in the city. If you’re looking for some unique items to add to your everyday wardrobe, visit Ragstock and Buffalo Exchange, which sell affordable and trendy vintage casual clothes. Kokorokokospecializes in vintage items from the 1980s and 1990s. Richard’s Fabulous Finds specializes in vintage menswear, and Silver Moon and Store B Vintage are home to pricier vintage black tie and designer items. Finally, Una Mae’s and Vintage Underground are Wicker Park thrift shop standbys. No matter your personal style or preferred price range, you’ll definitely leave Wicker Park with an exciting, unique vintage item!
Tours
Chicago River Tours
Chicago is a huge city with so much to offer, so it’s easy to get overwhelmed by the vast number of attractions. Let a Chicago native show you the best of what this city has to offer on a guided tour! Some of the most popular tours in Chicago, favored by both locals and tourists, are River Architecture Tours. Once you purchase a ticket, you can hop on a double-decker boat and let a seasoned tour guide show you the secrets behind some of the amazing, unique buildings that line the Chicago River. These tours are eye-opening and educational, but also allow you to enjoy the open air and relax as you cruise down the river.
FREE CHICAGO WALKING TOURS FULL CALENDAR
Walking Tours
If you’d rather get around on foot, consider a walking tour of the Loop. Chicago’s main downtown district is full of gorgeous pieces of public art, scenic views of the Chicago River and Lake Michigan, and towering skyscrapers. A walking tour of the Loop will take you past some of Chicago’s key landmarks, including the Riverwalk, Daley Plaza, and the Chicago Cultural Center. If this is your first time to Chicago, a walking tour can be an excellent way to experience the best of what the city has to offer, learn interesting tidbits about Chicago’s history, and stretch your legs. Even if you’ve visited Chicago before, there’s always something new to learn about the city’s various landmarks.
Food Tours
If your main priority during your stay in Chicago is to experience its vibrant food culture, don’t hesitate to book a food tour. Chicago is well-known throughout the globe for its unique staple foods, like deep-dish pizza, the classic Chicago hot dog, and Italian beef sandwiches. However, with so many establishments claiming to serve the city’s best versions of these Chicago classics, it’s difficult to decide where to eat! A food tour will take you around town to sample the best food Chicago has to offer, allowing you to stop in to try both famous establishments and lesser-known gems. In addition to tasting some of Chicago’s most delicious food, these tours will also take you to some of the same landmarks as a regular walking tour, so you get the best of both worlds!
Unique Tours
If you’re looking for a little more of an exciting tour experience, several companies also offer helicopter tours of the city. These tours are definitely much briefer than a walking or boat tour, with flight durations ranging between 10 and 30 minutes, but they’re a picturesque and unforgettable way to see the entire city from a birds-eye view. Different helicopter tour packages will offer you different flight plans, but in general, you can expect to see iconic Chicago landmarks like the Willis Tower, Lake Michigan, Navy Pier, and Wrigley Field during your tour. Some companies even offer private tour packages, where you’re guaranteed to experience the majesty of Chicago from above with just you and your party. Of course, you’re also going to pay more to book a helicopter tour than a walking or boat tour, but for thrill-seekers looking for a unique experience, a helicopter tour is well worth the price tag.
Shows
Chicago has an unparalleled live entertainment scene, with offerings that range from musicals and plays to comedy to live music. It’d be a crime to leave Chicago without catching at least one show during your stay, but with so many options to choose from, it’s understandable if you end up seeing a show every night! Chicago has a robust theater scene. Many popular shows that debut on Broadway in New York, like Hamilton, The Book of Mormon, and Waitress, call Chicago their second home. Tickets for Broadway shows in Chicago are slightly less expensive than those in New York, but the performance quality is unaltered. Of course, it’s still a good idea to purchase your tickets in advance, especially if you’re trying to see an incredibly popular musical like Hamilton or Dear Evan Hansen.
Comedy
Chicago’s premier comedy school and club, the Second City, is renowned the world over for producing some of the greatest comedic talents of our time. Many of its most notable alumni went on to make a name for themselves on Saturday Night Live, including Tina Fey, Amy Poehler, and Chris Farley. Other famously hilarious former Second City players include Stephen Colbert, Amy Sedaris, and Steve Carell. The Second City still puts on live improv and sketch comedy shows every single night, so no matter what day of the week or month of the year you’re planning to visit Chicago, you can count on the Second City to provide you with an evening full of entertainment and laughter. Tickets are available on their website.
Music
Chicago’s House of Blues serves double-duty as a restaurant and live entertainment venue. Each Sunday, they host a gospel brunch that allows you to enjoy soulful live music as you chow down on their all-you-can-eat buffet. In the evenings, they feature a variety of live musical acts, ranging from Michael Jackson tribute concerts to burlesque cabarets to concerts by artists like Lupe Fiasco, All Time Low, and Amine. It’s a good idea to buy tickets to one-night-only concert dates far in advance, but even when House of Blues isn’t hosting a big-name concert headliner, they still feature live blues and jazz music almost every night.
Nightlife
The fun in Chicago doesn’t end when the sun goes down — Chicago is also home to great bars, speakeasies, and clubs. If you’re 21 or older and are looking for a great place to party, dance, or enjoy some live music or performances, Chicago is absolutely the place to be! The Chicago Magic Lounge is one of the newest and hottest nightlife spots in Chicago. Their cocktails are all magic-themed, with names like “Sleight of Hand” and “Smoke and Mirrors.” Depending on which night you’re going out, you can enjoy jazz music or a live magic show as you drink!
Winter’s Jazz Club is one of the most highly-rated jazz lounges in the entire city. Almost every night, this bar and lounge host different jazz musicians. You can check their performance schedule on their website if there’s a specific performer that you’re itching to see during your stay. A spot in the listening room needs to be booked in advance, but specific seats within the area are first-come, first serve, so arrive 20 minutes early if you want to sit up front. Winter’s Jazz Club allows underage patrons between 12 and 20 to enjoy the listening room, too, provided that they’re accompanied by a parent or legal guardian, so you can bring the kids along too!
The iO Theater is another of Chicago’s most popular improv comedy clubs. They host different improv and sketch comedy shows every single night. Their signature improv performance is performed by members of the theater’s comedy troupe, collectively called Harold Teams. Each show begins with an audience suggestion and grows to incorporate different bits and characters that all revolve around that suggestion. The theater also hosts over a dozen featured shows with open runs. As you enjoy an uproarious comedy set, you can enjoy drinks, burgers, flatbreads, salads, and more!
Headquarters Beercade in the River North neighborhood is a unique arcade bar, meaning that as you enjoy a drink from their extensive selection of beers and cocktails, you can play any one of their vintage arcade games for free! They feature over 65 classic games like Frogger, Donkey Kong, Street Fighter, and Pac-Man, as well as a wide variety of pinball machines. Their event calendar also features exciting theme nights such as an annual boozy Disney movie sing-along, a monthly geek-themed burlesque show called Nerd-lesque, and a rotating roster of DJ sets. If you’re looking for a fun night out with friends that add in unexpected elements of childhood nostalgia, be sure to make a stop at Headquarters Beercade!
Enjoy Chicago!
That might have seemed like a whole lot of information, but that was just a quick rundown of some of the highlights of Chicago’s places to stay, restaurants, and things to do. There’s so much that this incredible city has to offer—you could stay here for an entire year and still not experience the totality of Chicago. If you’re looking for more ideas on how to spend your time in Chicago without spending all of your money, check out our blog, which is full of great tidbits about interesting attractions in the Windy City!
