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20 Best Things to Do in Chicago in Summer

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I am sharing the 20 Best Things to Do in Chicago in Summer so that you can make the most of the warm weather. The city joyfully springs to life during the summer and is bursting with activity and ways to spend time outside.

20 Best Things to Do in Chicago in Summer:

20 Best Things to do in Chicago in Summer

1. Go to a Cubs Game

It isn’t summer until you go to a Cubs game at Wrigley Field. I like to go to a game or two each summer because there is nothing more American than drinking a beer and watching a game while sitting in the sun. And Wrigley is gorgeous. If you aren’t really into baseball –  you can opt to see a concert at Wrigley instead of a game.

20 Best Things to Do in Chicago in Summer

2. Bike the Lakefront Path

Charles and I love to rent bikes and to bike from North Avenue Beach to Andersonville for lunch, it’s a really fun way to spend a warm day, and Andersonville is one of my favorite neighborhoods.

3. See a Movie in the Park

The Chicago Parks District hosts movies in the park all over the city – so grab a blanket and pack a picnic and head to the park to watch a movie outside. And a heads up… be discrete with any alcohol that you may bring, since drinking in public isn’t legal. Keep your beverages hidden and pour them into a cup.

20 Best Things to Do in Chicago in Summer

4. Green City Farmers Market

Did you know that Green City Farmer’s Market has three locations now? It takes place in Lincoln Park, the Park at Wrigley (a beautiful spot next to Wrigley Field), and in the West Loop! I like to go to the market in Lincoln Park on Wednesdays when it isn’t crowded, it is definitely one of the best things to do in Chicago in summer.

5. Jazzin at the Shedd

This Wednesday jazz concert series at the aquarium’s terrace is the place to soak in some of the best views in the city. Plus it is a fun opportunity to visit the many animals at the aquarium!

20 Best Things to Do in Chicago in Summer

6. Rooftop Cocktails

Chicago has lots of places to enjoy a rooftop cocktail. Some of my favorites are Hotel Lincoln, Cindy’s Rooftop, Raised, London House, Drumbar, and Boleo.

7. Fireworks

Fireworks are launched from Navy Pier every Wednesday and Saturday of the summer. Cindy’s Rooftop and the terrace at the Shedd Aquarium are two of the best places to watch them.

20 Best Things to Do in Chicago in Summer

8. Music Festivals

Lollapalooza, Pitchfork, Windy City Smokeout, Lake Shake, Mamby on the Beach, Spring Awakening, Riot Fest … there is no shortage of weekend-long music festivals in Chicago in the summertime.

9. Street Festivals

Most neighborhoods host a street fest – or two – in the summer. The Old St. Pat’s World’s Largest Block Party, the Sheffield Garden Walk, and the Old Town Art Fair are some of my favorite things to do in Chicago in summer.

20 Best Things to Do in Chicago in Summer

10. Food Festivals

So there isn’t much difference between some of the street fests and some of the food fests – there is food at both, but some festivals are definitely based around food. These include Taste of Chicago, Rib Fest, Taco Fest, Craft Beer Fest, Taste of Randolph, Oyster Fest, Chicago Gourmet, and Taste Talks.

11. Randolph Street Market

This antique market in the West Loop is the largest in America! It takes place outside on Randolph Street on the last weekend of the month from May – September.

12. The Lincoln Park Zoo

The Lincoln Park Zoo is always a blast – and the zoo hosts a variety of events each summer. Events include 21+ events like Craft Beers at the Zoo, the Zoo Ball, and Adults Night Out.

20 Best Things to do in Chicago in Summer

13. Sip a Negroni Slushie at Parsons

Parsons has one of the best patios in Chicago, and their negroni slushies are one of the most famous cocktails in the city.

14. Eat Outside!

Is there anything better than a leisurely meal outside? So many of Chicago’s restaurants have outdoor spaces. Some of my favorite places to dine al fresco are Big Star, Homeslice, Mia Francesca’s, The Dawson, Piccolo Sogno, Fireside, and Parlor. Plus! Small Cheval in Old Town is opening up a 100-seat patio this summer!

20 Best Things to do in Chicago in Summer

15. Play Volleyball on the Beach

Out-of-towners are often surprised to learn that Chicago has miles of beaches – we also have hundreds of volleyball courts. You can opt to join a volleyball league, or just reserve a court for a weekend game.

16. See Shakespeare in the Park

Shakespeare in the Parks brings theater to Chicago parks. The annual series tours Chicago parks for free performances.

20 Best Things to Do in Chicago in Summer

17. Shedd BLU

The annual fundraiser for the Shedd Aquarium is one of our favorite events of the summer. Presented by the Auxiliary Board, Shedd BLU is attended by 20 and 30 somethings and it brings together food and drinks from top restaurants, aquatic performances, dancing on the terrace, and fireworks. It’s one of the best Saturday nights of the summer.

18. See a concert at Pritzker Pavilion

A series of 10 free concerts take place between June 18 and August 16th. The music series features a wide range of musicians including jazz, indie rock, blues, salsa, and folk.

20 Best Things to do in Chicago in Summer

19. Cruise Lake Michigan

Rent a sailboat from Belmont Harbor if you know how to sail. Or go on a brunch, lunch, or dinner cruise with Odyssey Cruises. Or set sail on the Tall Ship Windy.

20. Air + Water Show

I have a long history of hating on the Air + Water Show, I actually leave town for it because I don’t love the noise of jets flying low over my home. But! Some people genuinely love the Air + Water Show, so I wanted to mention it. This is one of the most popular things to do in Chicago in summer.

Not in Chicago – but getting a mention: Ravinia

Ravinia combines music with picnicking. Buy tickets, pack a picnic, and grab a spot on the lawn. You can picnic while you listen to music. This summer performers including Diana Ross, Alison Krauss, Seal, Mary J Blige, Sugarland, OAR, The Beach Boys, and 50 Cent are taking the stage. Isn’t that one of the most random lists you have ever read in your life?

Want to save this list of 20 Best Things to Do in Chicago in Summer for later? Here is an image for you to pin:

20 Best Things to Do in Chicago in Summer - make the most of the summer

Jann Olson

Thursday 14th of June 2018

Hoping to visit someday, so pinning this for future reference. Glad you got to have so much fun! Thanks for sharing with SYC. hugs, Jann


Saturday 9th of June 2018

So many fun things to see and do!


Wednesday 6th of June 2018

That last one does have a really random list of artists. LOL I like some of them though. Thanks for sharing all of these. I really want to get back to Chicago and going in the summer sounds like a great time.



Wednesday 6th of June 2018

Yeah you never know who will play at Ravinia. It isn't a festival, it is a venue, so they aren't all playing together!

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