My Chicago Summer Bucket List this year

June 1, 2023

Chicagoans live for our summer! Well, at least I do. It’s my absolute favorite because winter. All because of winter…..So we created our Summer Bucket List very early in the season because summer is jam-packed! Patio brunches, rooftop drinks, picnics in the park, food festivals, outdoor concerts…and anything near or on the water, of course! There is a little something for everyone ranging from FREE to ticketed events.

Here’s my 2023 Chicago Summer Bucket List for you to check out!

Roscoe Village Burger Fest

Roscoe Village Burger Fest (July 7-9) 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.

Roscoe Burger fest is my absolute favorite festival in Chicago!

Rent a boat 

My friends and I do this 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 beach day at the 31st St. 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.

Attend Windy City Smokeout

Windy City Smokeout is one of the hottest events during Chicago summer! Zach Bryan, Darius Rucker, Luke Bryan, the Zac Brown Band, and more perform during the festival running July 13-16, 2023. 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 the 4-Day pass is already sold out! I would grab tickets while they are still available!

Chicago Windy City smoke out needs to be on everyone's summer bucketlist!

Attend the 52nd Annual Pride Parade

This is one of the best days in Chicago! It starts at noon on June 25 and begins at Montrose and 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.

Hyde Park Summer Fest

The Hyde Park Summer Fest is a ticketed event running June 17-18 at Midway Plaisance Park. Big-name acts this year at 2 Chainz, Clipse, and Lil’ Kim! Manny and I are going with some college friends this year, can’t wait!

Flavors of Albany Park

You have to try the Flavors of Albany Park crawl on June 21! 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!

Music and Movies at Millennium Park

The Millennium Park Summer Music Series runs Mondays and Thursdays from June 22-August 21, 2023. 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, but I haven’t seen anything for it this year.

The Millennium Park Summer Film Series runs Tuesdays from July 11-August 29, 2023. Standout choices are Black Panther: Wakanda Forever, Clueless, Top Gun: Maverick, Barbershop, and Everything Everywhere All at Once. 

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.

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!

Old Town Art Fair

The Old Town Art Fair is June 10-11 in the Old Town Triangle Historic District. They’ll have a garden walk, live music, a food court, and a children’s corner.

Montrose Beach for Chicago Air & Water Show Practice 

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 August 18 to watch the Air & Water Show Practice. Pack a picnic or get some food at The Dock at Montrose Beach. 

Farmers Markets

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

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 there will be a different restaurant popping up like Manny’s Deli, Birrieria Zaragoza, and J.P. Graziano!

Sno-ball from the Ina Mae walk-up window

Ina Mae is quickly becoming one of my favorite restaurants! They’ve got boozy sno-ball cones you can order from their to-go window and I can’t wait to try one of their specialties or make my own. Plus, every Thursday is Funk & Frozen Thursdays where you can get $10 boozy frozen cocktails and $7 Funktytown Brewery 16oz cans with live music.

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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