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Because you can't just be lying on your face all the time.
The Chicago Public Library - Get a free library card and gain access to books, ebooks, movies, and music that you can check out, among other things. Yes, you can burn the CDs to your computer and I did this all the time growing up. Also, they ended late fees, so you don't have to worry about those. Huge calendar of free events of all kinds all over the city.
The Art Institute of Chicago - Has periodic free admission days that change seasonally; make sure to reserve in advance. Also free overall to WIC cardholders.
Chicago Park District - Has a lot of free summer events open to the public including dancing, music, rock-climbing, crafts, and outdoor movies.
Heritage Asian Art Museum - Free every third Thursday night of the month.
Garfield Park Conservatory - free to the public; requires reservation in advance. Look at some nice plants.
Lincoln Park Zoo - Always free! Daily seal training and ape cognition and care events.
Adler Planetarium - Free on Wednesdays from 4pm-10pm; otherwise EBT and WIC recipients receive admission at $1 per group member which includes a free show, or $5 to include two shows.
Chicago Cultural Center - Always free; has periodic new art installations on the top floor.
University of Chicago Mindworks Lab - Behavioral science exhibit and working lab, always free to the public.
The Museum of Science and Industry - Free entry to EBT or WIC cardholders; also generally free on a bunch of random days listed here.
The Field Museum - See Sue the Dinosaur and other natural history exhibits. $3 to anyone presenting an EBT or WIC card (tickets must be purchased on-site).
Art on the Mart - Digital art exhibition projected onto the outside of Merchandise Mart
Shedd Aquarium - Free on select days, as well as any time to EBT cardholders.
Ukranian Institute of Modern Art - Donation-based admission; sometimes has events that have a "suggested donation" entry fee but no fixed cost.
National Museum of Mexican Art - Always free to the public!
Chicago on the Cheap - free events aggregator that includes museums, music, fitness classes, tours, and festivals.