Ditch the overpriced tourist traps and get ready for an adventure that’ll keep your wallet happy. We’re here to help you have a blast in the Windy City, laugh plenty, and still indulge in that iconic deep-dish pizza. Let’s get moving!
How to Get from the Airport(s) on the Cheap
Chicago’s got two main airports: O’Hare and Midway. O’Hare is kinda like the mothership—big, busy, and you’re likely to get lost. Midway, on the other hand, is more like the chill cousin with less drama. But here’s the tea: both airports have affordable ways to get downtown.
From O’Hare, hop on the Blue Line (yeah, it’s an L train—like in every Chicago TV show). It’ll cost you just $5 to get downtown in under an hour. Midway’s got the Orange Line, and for just $2.50, you’ll also be whisked downtown in 30-40 minutes. Uber or Lyft? Sure, if you like splurging on traffic.
Public Transport in Chicago: Actually Useful?
Say what you will, but the Chicago Transit Authority (CTA) is legit. You’ve got the L trains (they’re elevated—hence “L”), buses, and a day pass that’ll only cost you $5. Pretty good deal, considering you get to sit back while the city’s scenery flashes by, occasionally interrupted by an intense saxophone solo from a busker. Plus, the L lines are colour-coded for easy navigation.
Enjoy Chicago on the Cheap (Or Even Free!)
You’re not made of money, and guess what? You don’t need to be. Here’s how to max out your Chicago experience with minimum financial input.
Cool Neighborhoods
Wicker Park is the place to be if you want to feel effortlessly cool. It’s home to vinyl stores like Reckless Records (where you can flip through records starting at around $10), quirky boutiques with one-of-a-kind fashion finds like Una Mae’s (think vintage and indie designer pieces, $20-$100), and bookshops that ooze nostalgia (yes, that’s a thing—think old paperbacks and cozy reading nooks at Myopic Books, where prices start around $5). Don’t miss the Flat Iron Arts Building, where you can wander through artist studios and check out their work—no charge, just good vibes. Bonus: Bucktown and Logan Square are just a short walk away, both bursting with trendy coffee shops like Ipsento 606 (great coffee for $3-$6) and vintage stores like Store B Vintage (where you can find cool retro finds starting at $15). Grab a coffee, snag a seat, and soak in the people-watching scene without paying gallery prices.
Nature & Picnic Spots
Millennium Park is iconic—and totally free. Check out “The Bean” (officially, Cloud Gate) and snap a selfie that makes your forehead look like it’s from another planet. Then walk over to Grant Park or head up to Lincoln Park, where you’ll find the Lincoln Park Zoo (did I mention it’s free?)—so you can see lions and tigers without the ridiculous admission fee. Beyond the Lincoln Park Zoo, you also have the Lincoln Park Conservatory, which is also free and features beautiful indoor botanical gardens. Between the conservatory and the zoo, you could easily spend half a day enjoying the sights without spending a cent.
If you’re up for a picnic, grab some goodies from a grocery store or hit up a street food vendor (mmm, Chicago-style hot dog). Lay out in Humboldt Park, with its lagoons and amazing Puerto Rican vibes.
During the summer, the Chicago Park District offers free outdoor movies in various parks. These events often feature popular classics as well as recent blockbusters, creating a cozy, community atmosphere perfect for all ages. Similarly, you can catch free concerts at the Jay Pritzker Pavilion in Millennium Park, where everything from classical orchestras to indie bands performs against the stunning Chicago skyline backdrop. The pavilion’s state-of-the-art sound system makes it easy to hear the music from anywhere on the Great Lawn. Bring a blanket, grab some snacks, and enjoy the music. You can also find pop-up food vendors selling local favorites like hot dogs and popcorn, adding to the festive vibe.
If you’re looking to escape the hustle of the city, North Park Village Nature Center offers free trails through woodlands, wetlands, and a prairie, covering 155 acres of preserved land. It’s the perfect place to get a dose of nature without leaving Chicago, featuring well-maintained walking trails, birdwatching opportunities, and interpretive signs that help you learn about local flora and fauna. The center often hosts educational programs that are free and kid-friendly, including nature-themed workshops, guided walks, and seasonal festivals that make it a fantastic spot for families looking to explore the outdoors.
Navy Pier Fireworks
During summer months, Navy Pier hosts free fireworks shows every Wednesday and Saturday night. You don’t even need to be on the pier—just find a spot along the waterfront for a perfect view. It’s a quintessential Chicago summer experience, and it’s totally free.
Chicago Riverwalk
The Chicago Riverwalk is free to explore and offers spectacular views of the city’s iconic skyscrapers. You can walk along the river, relax on one of the many seating areas, or take advantage of free events, art installations, and entertainment often hosted during the summer. If you want to spend a little money, consider grabbing a snack or a drink from one of the affordable vendors along the walk.
Foodie Experiences on the Cheap
Skip the sit-down deep-dish spots and hit up Portillo’s for a classic Chicago hot dog (dragged through the garden—yes, it’s got all the toppings like mustard, relish, onions, tomato, a pickle spear, sport peppers, and celery salt). It’s a full meal for under $6 and a quintessential Chicago experience. If you’re more of a pizza person, grab a slice at Art of Pizza, where slices start at around $4—way cheaper than the big names like Giordano’s or Lou Malnati’s, and many locals swear it’s tastier.
Don’t sleep on Maxwell Street Market on a Sunday, either. You can score some amazing street tacos for as little as $2 each from vendors like Rubi’s Tacos, where you can watch the tortillas being handmade right in front of you. Not only is the food delicious and affordable, but you’ll also be surrounded by vintage stalls selling everything from old records to unique trinkets, plus live music that adds to the lively atmosphere. It’s basically a flea market-meets-foodie heaven—perfect for a Sunday outing that won’t break the bank.
Museums: Which Ones Are Free?
The Chicago Cultural Center is always free and offers a rotating selection of exhibits and cultural events that are definitely worth checking out. If you’re into contemporary art, The Museum of Contemporary Art is free on Tuesdays for Illinois residents. For history lovers, The Chicago History Museum offers free admission on select Mondays, giving you a peek into Chicago’s fascinating past. And, of course, The Art Institute of Chicago has free admission for Illinois residents on Thursday evenings—perfect for getting your art fix without spending a dime.
Offbeat Adventures
Visit The Rookery Building, an architectural gem designed by Frank Lloyd Wright, which was also a filming location for The Untouchables. Fans of Shameless can head to the South Side to see the Gallagher House (located at 2119 S Homan Ave), though remember it’s a residential neighborhood, so be respectful. The Marina City Towers, famously known as the ‘corn cobs’, also make appearances in several shows and are an iconic sight along the Chicago River.
And if you’re up for a bit of a trek, take a ride up to Winnetka to see the Home Alone house—yes, the actual one from the movie. It’s worth the nostalgia trip, especially if you snap a photo pretending to be Kevin McCallister.
Sports on a Shoestring
The Lakefront Trail is an 18-mile path along Lake Michigan that offers beautiful views of both the skyline and the lake. You can bike, walk, or jog while passing by popular beaches, parks, and attractions like Navy Pier and Museum Campus. Biking along the Lakefront is a great way to explore Chicago’s diverse neighborhoods and waterfront. Divvy Bikes rentals are available for just $16 per day—way cheaper than a Peloton membership and infinitely more scenic.
Then there is the 606. It’s an old elevated rail line turned into an urban trail that stretches for 2.7 miles, connecting several neighborhoods like Wicker Park, Bucktown, and Logan Square. You’ll pass through cool street art, green spaces, and get an authentic feel for the real Chicago beyond the touristy spots. You can also walk the trail if biking isn’t your thing, and stop along the way at the various parks and overlooks for a great view of the city skyline.
The Tourist Stuff: Just One Paragraph
Alright, let’s address the big one: The Willis Tower Skydeck. Do you want to stand on a glass ledge, 103 stories above the ground, to contemplate the meaning of life and question why you spent $35 on it? I mean, sure, if you’re into that kinda thrill. It’s fun, but the view from North Avenue Beach at sunset is free—and arguably just as breathtaking.
Best Time to Visit Chicago
Chicago winters are basically a game of “How many layers can you put on before you can’t move?”, so unless you’re into that, come in late spring, summer, or early fall. You get the warm weather, the lakefront vibes, and the festivals (seriously, Chicago has a festival for everything).
How Expensive Is Chicago?
Let’s break it down so your wallet doesn’t cry.
Food
Lunch can be as cheap as $5 if you’re cool with grabbing a hot dog or tacos from Maxwell Street. Dinner? A deep-dish pizza split between friends might set you back $12 each. Alternatively, Italian beef sandwiches at Al’s Beef are filling and under $10.
Drinks
Coffee: $3 at a hipster cafe. Beer: $5 at a dive bar. Wine? Chicago’s not Paris, but you can still get a glass for $8-10 if you’re feeling fancy.
Accommodation
Hostels like HI Chicago will run you $40 a night. Budget hotels? You can find something decent for under $100 if you book in advance. Or just couch surf—you’ll get local tips and hopefully some free breakfast out of it.
Chicago’s got it all
The architecture, culture, food, and those deep-dish pizzas that’ll make you question your relationship with New York-style slices. Whether you’re broke or ballin’ on a budget, there’s a way for you to soak up the city without breaking the bank. Get ready for the bean selfies, street tacos, and hopefully not getting lost on the L. Welcome to Chicago, fam!