15 Fun & Free things to do in Chicago

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Mini shopping spree in your favorite online store or bunch with a dear friend? Fancy new car or the 3-week trip through China you’ve been dreaming of for years? Which would you choose? Which would make you happier?

Did you know there have been a bunch of studies that have shown that the things that make us happiest in life aren’t really things we have, but rather the experiences we have?

When we buy things, like a new car or a new pair of diamond earrings, we may experience the giddy joy of ownership for a short while, but these studies show that that happiness we get from buying doesn’t last nearly as long as the happiness we get from spending that same money on an experience – like a vacation or a night out with the girls or a mani/pedi with mom.

Those types of experiences have been shown to give us much longer-lasting happiness.  

The good news is that your experiences don’t need to be expensive. There are a lot of fun experiences you can have for free or almost free in just about any area of the country you can think of.

Case in point, I was just in Chicago this week.

My cousin and I like to make the relatively short jaunt down there from Wisconsin every once in a while, just to get away for a night, catch up with each other and get a taste of the Windy City life. It turns out that Chicago has a bunch of stuff you can do for free. A few of these things we’ve done and some are still on our to-do list for next time we get down there. If you’re around Chicago (or within a few hours drive) you might want to check them out.  

Free or nearly free things to do in Chicago

It's free to visit the "bean" in Millennial Park

1) Millennium Park  – Yes, it’s the home of the Bean! O.K., the name of the sculpture is actually Cloud Gate. It was created by Anish Kapoor between 2004 and 2006. It’s got to be one of the most fun places to take selfies ever because of what the curves of the sculpture do to your image. Even kids will have fun with this sculpture. Also in Millennium Park are free gardens and fountains and the Jay Pritzker Pavillion where they host free concerts and film screenings. Just bring a blanket and a picnic and you’re all set for an evening of free entertainment.

Here in winter? No worries, bring your skates and skate away under twinkling tree lights. Don’t have skates, you can rent them for $12-$14 and you can even get free skating lessons. Big into ice skating? Then check out the Maggie Daley Park Skating Ribbon next to Millennium Park where you can skate for free through beautiful sculptures along a winding pathway with the city lights behind you. The Skating Ribbon is also free.  Millennium Park is located at 201 East Randolph Street. 

2) The Lincoln Park Conservatory and Gardens  is definitely on my list to visit next time we go. There are a variety of themed gardens outside you can wander through and there is also a gorgeous conservatory that was built between 1890 and 1895 that has 4 different display houses, the Palm House, the Orchid House, the Show House, and the Fern Room.  The Lincoln Park Conservatory is located at 2391 N. Stockton Drive. 

Visit the Chicago Cultural Center for Free!

3) Chicago Cultural Center  – Opened in 1897 this building known as “The People’s Palace” offers, art exhibits, lectures, performances and film screenings and all for free. I’m definitely looking forward to checking out the 38-foot diameter dome made by Tiffany Glass out of 30,000 individual glass pieces. It’s the largest Tiffany dome in the world and you can get free tours of this gorgeous building at 1:15 PM Wednesday-Saturday. The Cultural Center is located at 78 E. Washington St. 

Walk through beautiful Grant Park and see Buckingham Fountain for free

4) Buckingham Fountain in Grant Park  – I dare you to try not to take any pictures of this beautiful water display. The Chicago skyline makes a great backdrop – or if you prefer in the other direction gardens and Lake Michigan give your photos a very different feel. There is a light show as well that is happens for 20 minutes every hour and is, of course, best viewed at night. The last light show starts at 10:35 PM. You can find the fountain at: Columbus Drive (301 East) and Congress Parkway (500 South) 

Field Museum of Natural History - Visit for reduced fees

5) Chicago has awesome museumsThe Art Institute of Chicago and The Field Museum of Natural History  just to name two. If you happen to be an Illinois resident you’re in luck because admission to the Art Institute is free for you on Thursday nights from 5:00-8:00. If you are under 14 admission is always free.  Teens from Chicago up to 18 years old can also enter for free. Just show your proof of residency. The Field Natural Science Museum has a couple of free days each year as well for Illinois residents. But there are a bunch of great museums which you can always enter for free, Illinois resident or not!  Here are just a couple: 

  • 6) Smart Museum of Art at the University of Chicago houses 15,000 objects from modern masterpieces to ancient Chinese artworks and just about everything in between. Besides the exhibits, they offer workshops, lectures, and performances. You can find the Smart Museum of Art at 5550 S. Greenwood Avenue. 
  • 7) Gallery in the Historic Water Tower is really handy to drop by and visit if you’re doing a little shopping on Michigan Avenue’s Magnificent Mile. The building itself is pretty cool as it looks like a miniature castle and it’s actually one of the few buildings to survive the terrible fire that ripped through Chicago in 1871. Exhibits change regularly. You can find this architectural gem at 806 N. Michigan Avenue. 
  • 8) The National Museum of Mexican Art features more than 9,000 pieces of art dating from ancient Mexico to the present time. The museum also offers special events and performances. The Museum of Mexican Art is located at 1852 W. 19th St. 
  • 9) The Oriental Institute  showcases the art and architecture of the ancient Near East (Egypt, Mesopotamia, Persia, Syria, etc.)   The Oriental Institute is located at 1155 East 58th Street (Suggested admission is $10.00 for adults.) 

10) Free Music – Chicago offers a bunch of free music opportunities in its parks. One I’m definitely going to want to check out is the Chicago Blues Festival which takes place in June and is the largest free Blues festival in the world. But if Blues isn’t your thing there’s Jazz, Classical, World Music and more. Check out some possibilities here: https://www.choosechicago.com/events-and-shows/festivals-guide/free-chicago-summer-festivals/ 

Free Blues at Buddy Guys at Lunchtime

11) Buddy Guy’s Legends – Want a little food with your music? Buddy Guy’s has awesome Blues music every night of the week. There’s a $10 cover charge at night and it can be a little tough to get a table (no reservations are accepted) but Wednesdays – Sundays they have an acoustic lunch set from 12:00-3:00 which is free for all ages. From 6:00 to 8:00 or 8:30 (depending on the night) there is an acoustic set that’s also free for all ages.  Buddy Guy’s is located at 700 S. Wabash.

12) Don’t want to go it alone? Want someone in the know to give you a little tour of whatever area of Chicago you’re interested in? Chicago Walking Tours  offers about 10 different tours with themes from Ghosts to the Riverwalk to the Magnificent Mile. There is no set charge you just pay what you feel the tour was worth at the end.  

Need more ideas for great deals on things to do in Chicago?  

13) The Lincoln Park Zoo  is one of the oldest free zoos in the country. It’s located next to the Lincoln Park Conservatory and also has ice skating during the winter months.  

14) Chicago Greeter neighborhood tours.  They’re 2-4 hour long walking tours that are customized based on your choice of location and your interests. They’re free but you need to book ahead at least 10 business days. 

Live Like a Queen on your 9-5 Pay! Book cover and description.


15) Clark House Museum is Chicago’s oldest surviving house and was built in 1836. This house survived more than one fire (including the Great Fire in 1871) and was moved several times. Now it resides in the Chicago Women’s Park, which is a pretty interesting destination as well.  The Clark House Museum is located at 1827 S. Indiana Avenue.

If you’re looking for great experiences and don’t want to spend a lot of money, those are just a few ideas to try out if you’re in or near Chicago. But you don’t even have to travel that far to enjoy a great experience with friends or family. Have a picnic in a nearby park or green space. Go for a hike, even urban hikes can be a lot of fun. Have some friends over for movie night and have everyone bring a different snack while you supply the beverages. What about a game night? Cards, board games, charades? If it’s nice out take it outside to the deck or the yard.

The old-fashioned fun can be some of the best fun. Use your imagination and keep your eyes open for more ideas on EasySimplicity.com

If you’re in the mood to visit Vegas check out 15 Fun & Free Things to do in Las Vegas

More in a New York State of mind? Check out 40 Fun & Free Things to do in New York City

Interested in starting a savings habit so that you can visit more exotic places someday? Check out 3 Steps to Starting a Savings Habit.

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