A local's guide to the [12+] best free summer activities Chicago has to offer

and some general ideas for non-Chicagoans too

On The Sunny Side #27 is a weekly round-up where I share a few sunny things that have brightened my days, what I’m reading, watching, and obsessing over too.

For four months out of the year, Chicago gets it’s time in the spotlight. I’m talking, of course, about summer in the city. There is nothing quite like a Chicago summer (I feel very passionately about this). Strolls along the lakefront trail or 606. Grabbing a dipped cone. Jumping in the lake. Oodles and oodles of farmers markets and street festivals.

There is no shortage of fun activities to do around the city in the warmer months! I’ve rounded up the best free activities and a handful of other low-cost recommendations the next time you need inspiration on how to fill your weekend or you’re visiting from out of town and want to live like a local.

So without further ado, let’s dive in.

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Bike, rollerblade, run, stroll the lakefront trail

One of my all time favorite Chicago summer activities. I’m not really a beach goer as I burn like a mofo but a casual stroll and/or bike ride on the lakefront trail? Ideal!

You don’t even need to own a bike. You can easily rent a Divvy (Chicago’s rental bikes) and zoom to your hearts content. I love stopping halfway through a ride to jump in the lake and cool off before hopping back on. I always try to stop for a sweet treat at Annette's Italian Ice to end the day.

Friday Morning Swims

Friday Morning Swim Club is a free, weekly meet-up at Montrose Harbor for people who appreciate slow mornings and Chicago’s unique landscape. Attend alone or with friends to swim and drink coffee with community members who enjoy social routine and activities that support organic conversation. This one is on my Chicago Summer Bucket List! I also think this would be a great activity if you’re new to the city.

Millennium Park’s Summer Music & Film Series

Pritzker Pavilion hosts free concerts every Monday and Thursday from June 26th - August 7th and free film viewings every Tuesday from July 1st - August 19th. Grab a blanket and pack a picnic to lounge on the great lawn. I’ve seen one of my favorite bands, Whitney, during the free summer music series and this years film series looks stacked (Wicked in the park… say less!)

Movie nights at local parks

Speaking of movies in the park, most of Chicago’s neighborhood parks offer free movie viewings. The City of Chicago has this handy-dandy PDF broken down by park and date with all the film titles scheduled for the summer from now until September 6th.

Read or picnic at Humboldt Park

Humboldt Park’s lagoon has its own inland beach but if swimming in the pond with Chance the Snapper doesn’t appeal to you, there’s plenty to explore in the 197-acre park. Humboldt Park is also home to Chicago’s Latin Jazz Fest and the annual Puerto Rican Festival.

Beach Day

There are so many different beach options in Chicago to chose from: Montrose, Ohio Street, Oak Street, Foster Beach, 12th Street Beach, or North Avenue. All are free, but not created equally lol. Some, like North Ave tend to be a bit more rowdy and depending on the day of the week can have volleyball leagues going on so take note.

If you’re looking for something more lowkey and willing to drive/pay $5 I’d highly recommend the beaches in Evanston as they’re cleaner and calmer (can you tell I’m not in my twenties anymore??)

BYOC date on the 606

Not *as* picturesque as the lakefront trail but equally enjoyable, is the 606. It’s the perfect walking trail for a bring your own coffee date for a walk and a yap. The 606 was previously an abandoned rail line turned walking path (think highline in NYC) and is 2.7 miles long. There are also so many great coffee shops directly located off trail exits, like one of my favorites Ipsento.

Free museum days

The Art Institute of Chicago offers free admissions for Illinois residents, Thursday evenings, June 1 – Sept. 25, 2025.

The Adler Planetarium is free every Wednesday evening from 4 – 10 p.m.

The Chicago History Museum offers free admission on select holidays. Upcoming dates include June 19, 21, and 28. July 4, 24, and 30. Aug. 13 and 28.

The Field Museum is free every Wednesday for Illinois residents.

The Shedd Aquarium offers Illinois residents free access to all permanent exhibits on select dates throughout the year.

Admission to the Griffin Museum of Science and Industry is free for Illinois residents on select dates throughout the year.

Free (street) festivals

Nearly every weekend in Chicago you can find a local street festival to enjoy. For a comprehensive list by neighborhood and dates, see here. Below is a look at my favorites that I never miss:

1. Do Division (already past)

2. Andersonville Midsommarfest (June 13 – 15)

3. Taste of Randolph (June 13 – 15)

4. Wicker Park Fest (July 26 – 28)

5. Northalsted Market Days (Aug. 9 – 10)

6. Renegade Craft Fair (Sep. 6 - 7)

Explore Harold Washington Library

If you’re downtown and are looking for something to do to beat the heat outside, I recommend exploring Harold Washington Library. Once you arrive take yourself up to the 9th floor and to enjoy the breathtaking Winter Garden. The glass roof highlights the enchanting architecture of the space with abundant natural light perfect for cracking open a book and cooling off.

Spend a Saturday at the Lincoln Park farmers market and zoo

My personal favorite farmers market in the city for its proximity to the lake and my favorite scone from Bennsion’s Bakery. I love nothing more than to spend a Saturday at the Lincoln Park farmers market. They have a great selection of vendors and if you have little ones with you, it’s a short walk to the Lincoln Park Zoo (always free).

Outdoor workout classes

Millennium Park Summer Workout Series, Gallagher Way fitness events, The Green at 320 or checkout neighborhood famers market schedules for free yoga and pilates classes! The Wicker Park farmers market offers these classes each weekend, weather dependent.

Don’t live in Chicago?

No worries, many of the activities I’ve rounded up can be easily replicated in different areas! All you really need to do is look into local park district offerings. I guarantee your town/city offers many of the same free summer activities with a different spin.

Spend time at you local library and complete the summer reading challenge! Invite friends over for a good old fashion movie night. Host a potluck bbq! Bike around your neighborhood. Take your yoga mat to a park with friends. You get my drift…!

Bonus: My favorite inexpensive summer activities in the Chicagoland area

1. Concerts at Ravinia is my happy place in the summer

2. Catch a Cubs or Sox game (if you’re just looking for vibes and aren’t a fan, Sox tickets will be cheaper)

3. Enjoy a dipped cone at Small Cheval

4. Rent a boat with friends (or find a FWB, aka Friend with Boat)

5. Book a trolley for a night of fun

6. Rent kayaks on the river

7. Learn about the city while taking in the views on an Architectural Boat Tour

8. Take the water taxi to Chinatown

9. Jazzin’ at the Shedd

   1. When: 5-10pm on Wednesdays, May 28 through August 27, 2025

   2. Cost: Adults $29.95, Children (3-11) $24.95

There you have it: a comprehensive guide to fill your Chicago Summer Bucket List. If you aren’t from the city but looking to visit, make sure to bookmark this for later and if you want more Chicago recs from yours truly, send me a DM or leave a message in the comments!

Until next time, MacKenzie