Occasionally overlooked in favor of coastal cities like San Francisco or New York, Chicago is one of America's best and somehow most underrated cities to visit.
Towering above the shores of Lake Michigan, Chicago is a city of incredible architecture, rich history, world-class museums, and a beautiful downtown area. The food scene in Chicago rivals any city in the country (there's much more to this place than delicious deep-dish pizza and Chicago-style hot dogs), the vibrant nightlife scene goes as late as 4 am, and the live music venues do it all, from the blues to punk and everything in between.
However, Chicago isn't always the cheapest city for a tourist. So we've put together this ultimate travel guide to show you how to visit Chicago on a budget.
Chicago on a budget: Know before you go
Embrace public transportation
Chicago's 'L' train can take you where you want to go. Plus, it's more budget friendly than an Uber. Grab a reloadable Ventra card at kiosks found in subway stations and the airport. You can add funds as needed or pay upfront for an unlimited pass of 1, 3, or 7 days.
Explore the neighborhoods
There's so much more to Chicago than downtown. Get out and explore the city's distinct neighborhoods – from West Loop and Wicker Park to Lincoln Park and Lakeview – and choose your favorite!
Dress for the weather
It's true, this city gets COLD in the winter and that wind is definitely no joke. But it also gets scorching hot, rainy, snowy, foggy, and darn near everything else in this city. Instead of trying to plan for Chicago's crazy weather, dress in layers that you can easily add or remove.
Smarter ways to park your car
If you have to drive in Chicago, be sure to download the Park Chicago app to easily pay for, extend, and register for street parking. If you'd rather park in a private parking space or garage, you can reserve and pay ahead of time with ParkWhiz and SpotHero.
Free and cheap things to do in Chicago
Stroll through Millenium Park
Located in the heart of The Loop, Millenium Park is a meeting place for both locals and tourists alike. The most popular attraction in this sprawling park is easily the famous Cloud Gate sculpture, better known as The Bean. Walk under this reflective archway and watch your distorted reflection change with each step. Then, do as every tourist has done before you and snap your very own Bean Selfie.
After you’ve posed with the Bean, explore the rest of Millenium Park by splashing around with the local faces of Crown Fountain or taking a break amongst the colorful flowers of Lurie Garden.
Get wild at the Lincoln Park Zoo
Believe it or not, one of the country’s best and oldest (4th oldest in North America) zoos is still free to visit. Located in, you guessed it, Chicago’s famed Lincoln Park neighborhood, the Lincoln Park Zoo is home to over 1,100 different animals and is constantly welcoming new species. As a bonus, the zoo’s Nature Boardwalk also offers an incredible view of the Chicago skyline along the South Pond.
Take in the Chicago skyline views from Navy Pier
Navy Pier, affectionately known as the “People’s Pier,” is one of Chicago’s most iconic attractions. Jutting out onto the waters of Lake Michigan, the pier is like a theme park within the city limits, complete with rides, restaurants, beer gardens, boat tours, dinner cruises, and, of course, the iconic 15-story Ferris Wheel. Most of the attractions on the pier cost money but strolling the pier while talking in the incredible views of the city along the Lake Michigan shoreline is completely free if you're on a budget.
Window shop your way down the Magnificent Mile
This 13-block stretch of North Michigan Avenue, known as the Magnificent Mile, is one of the most iconic retail, dining, and hospitality destinations in the world. The bustling avenue, stretching from the Chicago River to Oak Street, is home to Chicago’s premier shops, restaurants, and hotels, making it a great place to do some window shopping and people watching. And if you need a pick me up as you take in the sites, leave some room in your budget for a pit stop at the world’s largest Starbucks!
Where to stay on a budget in Chicago
HI Chicago - The J. Ira and Nicki Harris Family Hostel
The Chicago outpost of this international hostel chain delivers the same high-quality experience that budget travelers have come to expect from them. HI Chicago is conveniently located in The Loop and less than a 10-minute walk from famous attractions such as The Bean and Willis Tower. Inside, the common areas are stylish and spacious, while the rooms – either dorm or private – are clean and comfortable.
As you might guess, Wrigley Hostel is located in the lively neighborhood of Wrigleyville, close to the world-famous ballpark of the same name. Thanks to its inviting common areas, this modern hostel gives more of a cozy ‘bed and breakfast on a budget’ feel. It has colorful dorm-style and private rooms, a communal kitchen, a BBQ deck, and a common room complete with tons of games such as pool, ping pong, and foosball. Guests also love the location of Wrigley Hostel, as it’s just a short walk to the Addison Red Line ‘L’ stop and close to some of the city’s best sports bars.
If you prefer to stay in the hip, boutique-style hostels when you travel, look no further than Freehand Chicago, located in the nightlife-rich neighborhood of River North. Here, Freehand takes a unique approach to budget-friendly accommodation, providing rooms – available in both dorm-style & private – that are modern and stylish, yet affordable. Downstairs, mingle with other guests at Broken Shaker, Freehand’s award-winning on-site cocktail bar.
Cheap flights to Chicago
Recently, Dollar Flight Club members have saved between 70-90% on cheap flights to Chicago. On average, our members spent $72 on their tickets to Chicago and saved over $157 per ticket. Here are a few samples of cheap flight deals that Dollar Flight Club members have received recently.
Nashville (BNA) to Chicago (ORD)
Price with Dollar Flight Club: $77
Average Price: $185
Los Angeles (LAX) to Chicago (ORD)
Price with Dollar Flight Club: $37
Average Price: $162
Dallas (DFW) to Chicago (ORD)
Price with Dollar Flight Club: $45
Average Price: $162
Best cheap eats in Chicago
Portillo’s is a true Chicago institution. Most of the locations are situated way out in the suburbs, but the location in Chicago’s popular River North neighborhood is perfect for fueling up during a long day of Chicago sightseeing.
It’s all about the Chicago comfort classics at Portillo’s, specifically the famous Chicago style hot dogs, which are piled high with mustard, celery salt, relish, chopped onions, sliced tomatoes, a pickle spear, and sport peppers on a steamed poppy seed bun. In addition to being delicious, the jumbo dog at Portillo’s is just a budget friendly $3.29. Just don’t forget to save room for their famous chocolate cake shake, made with an actual blended piece of chocolate cake!
Al’s #1 Italian Beef
Though not as popular with tourists as deep dish pizza or Chicago style hot dogs, the Italian beef sandwich is another certified Chicago food icon. And there is none more iconic than the Italian beef at Al’s #1 Italian Beef in Little Italy, especially if you’re on a budget.
For just $6.49 at Al’s #1 Italian Beef, you can get the famous Italian Beef sandwich, made with seasoned roast beef on a french roll and dipped in beef jus. And if you really want to eat your Italian Beef the right way, test your form with Al’s trademarked ‘Italian Stance’.
Though there’s certainly stiff competition in the city, Chicago’s best falafel can be found at Sultan’s Market.
Specializing in Middle Eastern food, Sultan’s Market serves up large portions of classics like rich, flavorful shawarma, falafel, hummus, baba ganoush and so much more. Plus, the prices here are more than reasonable for any budget. $6 gets you their traditional falafel sandwich topped with onion, olive oil & lemon juice. If you’ve really worked up an appetite, you can treat yourself to a heaping shawarma plate just $5 more.
Sultan’s Market has 3 locations: Wicker Park, Lincoln Park, and Logan Square.
Start planning your trip to Chicago
Contrary to popular belief, a trip to The Windy City doesn’t have to break the bank. With a little patience and planning, you can have an amazing time in Chicago on a budget.
So whether you've always wanted to go on a Chicago architecture boat tour or dream of one day catching a game at Wrigley Field, be sure to save this budget travel guide, and sign up for cheap flight alerts today!
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BY: ZACH ANDERSON, CONTENT MARKETING & FLIGHT EXPERT
Zach is a digital marketer, copywriter, and flight deal expert at Dollar Flight Club where he helps 1 million people travel more. As a digital nomad, he is deeply passionate about location independence, Thai food, and helping others see the world affordably.