Chicago Summer Guide: The Best Things to Do!

May 17, 2024

Chicagoans live for our summer! It’s my absolute favorite because of my winter hibernation. Our Chicago Summer Bucket List is jam-packed! Street festivals, outdoor concerts, picnics in the park, food trucks, rooftop drinks…and anything near or on the water, of course! There’s a little something for everyone ranging from FREE to ticketed events.

Here’s The Chicago Good Life Summer Guide: Best Things to Do!

Get on the Water!

Whether you rent a boat, kayak the river, or take a guided tour, experiencing Chicago from the water is the best! There are plenty of options for architecture and history tours on the river; some even take you out on the lake! The 90-Minute Chicago Architecture Boat Tour and Chicago Fire Boat Tours are on sale on Groupon right now!

My friends and I rent an e-boat every summer! Last year, we did it with the kids too. It’s so easy and a great way to get on the water. The Electric Boat Company offers different size boats and different dock locations, we love the Rockwell location because it’s less crowded. It’s BYO food, drinks & speakers, drive yourself or rent a captain, and perfect for a girlfriend get-together. I feel like it’s a must-do on your Chicago Summer Bucket List!

Have a drink on a hotel rooftop

Nothing beats having a cold drink on a hot day on a breezy rooftop! My favorites are The Cabana Club (they sell day passes under $20) at The Robey Chicago and NoMI at Park Hyatt for an espresso martini – it’s one of my favs in the city.

Have a beach day

Our favorite beach is the 31st Street Beach. Why is this one of my favorite beaches? It’s less crowded, has great views, there is a playground/splash area, and Pier 31 Restaurant has live music, food, and drinks. Other popular beaches are Oak Street Beach, North Avenue Beach, and Hollywood Beach!

Have a picnic at Promontory Point

Promontory Point is one of Chicago’s newest official landmarks! It’s such a nice, quiet, piece of land on the South Side with some great views. It was also the location of Barack and Michelle’s first kiss! 🙂 The beach is right next to it and you could head to 57th for shopping and eating after.

See the Chicago Air & Water Show Rehearsal

We have watched the Air and Water show practice since Noah was little. It’s way less crowded and literally the same thing as the real show. Head out to Montrose Beach on Friday, August 9th to watch the Air & Water Show Practice. Pack a picnic or get some food at The Dock at Montrose Beach. See more here!

Take a Staycation with a Pool

We have a big list of hotels with pools here!

Visit a Park District Pool

We love to take advantage of the Chicago Park District pools! They are free! The best ones we have been to are Wrightwood Pool and Portage Park. Wrightwood is great for kids, it’s small but does the job! Portage Park has two pools, diving boards, and a toddler pool with a slide! All CPD pools have different hours and lots of rules, but again, they are free and totally worth it!

Attend Jazzin’ at the Shedd

Jazzin’ at the Shedd is SO fun! Every Wednesday in the summer beginning June 5, the aquarium stays open until 10pm. They have a live band, refreshments, and you can roam the aquarium!

Flavors of Albany Park

You have to try the Flavors of Albany Park crawl on Wednesday, June 26! We literally ate our way down Lawrence last year, tried foods from all over the world, and had the best time. One of our first stops was Nighthawk Chicago for housemade sangria. It was a great way to start the night and they have a huge patio in the back! My absolute favorite stop was Pancit Bihon from Subo Chicago. It was such good Filipino food and I can’t wait to go back. There were 18 stops on the crawl last year and by stop 9 I was already so full! This is so worth the $40 ticket price!

Explore Chicago Parks

I’m such a fan of the Chicago Park District! Between the 8800 acres of green space and all the event programming, we are so fortunate to have so many parks to explore. The new playground in Brighton Park is so cool! We also love the Garden of the Phoenix in Jackson Park. The La Ronda Parakata Gathering Space in Burnham Park is a hidden gem near 31st Street Beach, too!

Explore a new-to-you Neighborhood

Chicago has 77 neighborhoods! How many have you been to? I recently explored Chinatown (watch here!) and had such a great time! We have a few guides for you here!

Have a Sweet Treat

There’s no shortage of ice cream shops and other cold-treat spots in Chicago! My favorites are Scooters Frozen Custard in Lake View, Margie’s Candies in Bucktown, Eli’s Ark in Wicker Park, and Mario’s Italian Lemonade in Little Italy!

Celebrate Pride

Chicago Pride Fest is June 22-23 in the Northalsted neighborhood. The 2024 Artist Lineup features Natasha Bedingfield, Sapphira Cristal (runner up of RuPaul’s Drag Race Season 16), and Bob The Drag Queen. The 53rd annual Chicago Pride Parade will be held on June 30 and it is one of the best days in Chicago! It starts at 11 am at West Sheridan and North Broadway in Uptown. The best viewing is the Boystown section of North Halsted, between Belmont and Grace. For a less crowded spot, try Broadway between Belmont and Diversey.

Windy City Smokeout

Windy City Smokeout, July 11-14 in the United Center Parking Lot, is one of the hottest events during Chicago summer! Thomas Rhett, Cody Johnson, and Carrie Underwood are the big headliners this year. BBQ from all over the country and local places like Bub City, Green Street Smoked Meats, Lillie’s Q, and  Smoque. It’s so much fun! Tickets are now on sale and I would grab tickets while they are still available!

Sundays on State

I always have a great time at Sundays on State! There are two dates this year – July 16 and August 13. They close State Street to traffic and have a big FREE block party with art, food, drinks, shopping, and entertainment!

Roscoe Village Burger Fest

Roscoe Village Burger Fest (July 19-21) is quite literally one of my favorite Chicago festivals. In my opinion, it’s a must-add to your Chicago Summer Bucket List. Over a dozen local restaurants participating, two stages of live music, arts & crafts, and a Kids Zone. Visitors even have the opportunity to vote for Chicago’s Best Burger! There is a $10 suggested fest donation at the door and the Kids Zone area is an additional ticket.


EEEEEATSCON is a restaurant festival featuring local businesses and fun food from across the country. This food experience runs July 13-14 at The Salt Shed. Manny and I had SUCH a great time last year!

And even more Festivals…

  • Do Division (May 31-June 2) – This festival in West Town has food trucks, retail vendors, a petting zoo, a mega slide, and tons of live music.
  • Greek Fest (May 31st – June 2) – Try Greek cuisine and wine in Lincoln Park. Last time we went, there was also a big kids area!
  • Hot Dog Fest (June 1-2) In Portage Park, they have bands and lots of unique hotdogs to try along with the classics!
  • Sheffield Garden Walk (July 20-21) – This free event is a self-guided tour throughout the Sheffield neighborhood. The Kids Fest is on Saturday, July 20 and it’s usually a pretty big area for the kids!
  • Polonia Fest (August 30-Sept 2)- Located in Jefferson Park, it has lots of different Polish food to try! They have live music and lots of local vendors.

Summer BBQ Pop-Ups at The Sportsman’s Club

This looks so cool! The Sportsman’s Club is in West Town and every Sunday this summer, they’ll have a different restaurant pop-up like 5 Rabanitos, Nine Bar, and Andros Taverna!

Attend a Farmers Market

Check out my huge resource of all the city farmers’ markets. Buy local and eat more veggies! It’s a win-win! 

Enjoy the Millennium Park Music & Movies Series

The Millennium Park Summer Music Series runs Mondays and Thursdays from July 1-August 8, 2024. Don’t miss the Tribute to Ramsey Lewis, Big Freedia, and Stephen Marley! You can bring small bags and coolers with your own food and non-alcoholic beverages or purchase from the concession stands! Last year, they had a Selena Tribute that was SO amazing, so save the date for September 6!

The Millennium Park Summer Film Series runs Tuesdays from July 16-August 20, 2024. Standout choices are E.T., Jurassic Park, Coco, Barbie, and Ferris Bueller’s Day Off. 

Have a Family Day at Navy Pier

Watch the full reel here of our entire day at Navy Pier with the kids! They absolutely loved the Flyover experience!

Catch an MLB or WNBA game

I can’t wait to go to my first WNBA game! White Sox tickets are cheap now and they have $5 dollar Tuesdays happening all season long. Select menu items are just $5 dollars like pizza, hotdog, popcorn, etc. The Cubs also have discount tickets for $10 here.

Take a Road Trip

Head to the Midwest Travel section for our road trip guides to New Buffalo, Mall of America, Wisconsin Dells, and more!

I hope you like some of these ideas on my Chicago Summer Bucket List! And if you need a full 3-day detailed itinerary, you can purchase a guide here: 3-Day Chicago Summer Itinerary!



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