GROUPON GUIDE TO WINDSOR

Free or Cheap Things to Do in Chicago: Fun on a Budget

Jun 26, 2025

chicago

Chicago might be home to towering skyscrapers, world-class museums, and some seriously iconic eats, but you don’t need deep pockets to enjoy the Windy City. Whether you're a local looking for weekend plans or a visitor trying to stretch your dollars, Chicago is full of free and cheap things to do. From stunning parks and historic neighborhoods to free festivals and budget-friendly eats, here’s how to experience the best of the city—without spending a fortune.


🌳 Explore the Outdoors for Free

Chicago offers plenty of outdoor adventures that cost absolutely nothing. Start with a stroll through Millennium Park, home to the iconic Cloud Gate sculpture (aka "The Bean") and the peaceful Lurie Garden. On a sunny day, head to Lakefront Trail, a scenic 18-mile path perfect for biking, jogging, or people-watching along Lake Michigan.

Other must-see outdoor spots:

  • Lincoln Park Zoo – One of the few free zoos in the country

  • The 606 – A converted rail line turned elevated trail, great for a walk or run

  • Humboldt Park Lagoon – A quieter green space with a boathouse and wetlands


🖼️ Visit Free Museums and Cultural Spots

Chicago is rich in culture, and many of its museums offer free admission days or permanent free exhibits.

  • The Art Institute of Chicago – Free for Illinois residents on Thursday evenings

  • The Museum of Science and Industry, Field Museum, and Shedd Aquarium – Offer free days throughout the year for IL residents (check schedules)

  • Chicago Cultural Center – Always free, and home to art exhibits, concerts, and the world’s largest Tiffany stained-glass dome

👉 Tip: Check out the Groupon museum deals in Chicago for discounted entry to even more attractions.


🎉 Enjoy Free Festivals and Events

Chicago’s neighborhood festivals are legendary—and many are free to attend!

  • Chicago Blues Festival (June)

  • Taste of Chicago (July)

  • Grant Park Music Festival – Free classical concerts in the park

  • Movies in the Parks – Catch free outdoor movies all summer long

During the Christmas holidays, don’t miss the Christkindlmarket or the Millennium Park tree lighting—both festive and free.


📅 Even More Free Events!

From summer festivals to lakefront movie nights, Chicago’s always buzzing with free things to do. Check these local event calendars for the latest:


🌭 Find Cheap Eats & Local Flavors

Yes, you can eat well in Chicago on a budget. Grab a slice of deep-dish at spots like Art of Pizza or a legendary Chicago-style hot dog at Portillo’s or Byron’s. Hit up food trucks, taco joints in Pilsen, or explore Argyle Street for affordable Vietnamese and Thai dishes.

👉 Save even more with Groupon restaurant deals in Chicago, including pizza, brunch, and international cuisine.


💰 Take Advantage of Local Discounts & Deals

Score Big Savings with Groupon

From immersive tours to comedy nights, Groupon Chicago deals offer serious discounts on activities like:

Other Local Hacks for Saving:

  • Free museum days: Many major museums offer monthly or weekly free days for IL residents.

  • Chicago Public Library’s Museum Passes: Check out a Kids Museum Passport or use Explore More Illinois to get free or discounted admission to top attractions.

  • Student & senior discounts: Ask about reduced rates at theaters, attractions, and transit services.

  • Chicago Greeter Program: Sign up for a free walking tour led by a local volunteer!


🚲 Walk, Bike, or Ride for Less

  • Rent a bike for just $5/day with Divvy, Chicago’s bike share program.

  • Hop on a Chicago Riverwalk self-guided tour, or just explore on foot—it's beautiful and totally free.

  • Want something more structured? Try a guided walking or boat tour with deals starting under $20.


🎯 Final Thoughts

With a little planning—and a few smart deals—it’s totally possible to experience the best of Chicago on a budget. Whether you’re wandering lakeside, admiring world-class art, or munching on a cheap slice of pizza, the city delivers big fun for little money. And if you're looking to do even more, check out all the latest Groupon Chicago deals here.

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