Chicago Travel & City Adventures

My Chicago Summer Bucket List this year

Chicagoans live for summer! We create 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 2022 Chicago Summer Bucket List for you to check out!

Watch a classic movie at the new Rooftop Cinema Club Chicago

Rooftop Cinema Club, opening May 26 with Ferris Bueller’s Day Off, is a new outdoor movie experience in the Fulton Market district. They’ll have family-friendly shows in the afternoon but evening movies are only for the 18+ crowd. Bring a blanket, grab some headphones and popcorn, and enjoy the views of the city while watching a classic movie!! A full food and bar menu from The Emily Hotel is also available to order throughout the film.

Add this rooftop cinema to your summer bucketlist this Chicago summer!

Lunch at Mima’s Taste of Cuba

This hidden gem in the Irving Park neighborhood has one of the best patios, you feel like you are on the island! Not only is their patio cute, their jibaritos are also really good. they have fun tropical drinks and beautiful murals along their walls. Definitely add them to your Bucket List this summer!

Mima's cuban cafe in Irving Park is so cute! Add this to your Chicago Summer Bucket List!

Vote for Chicago’s best burger at Roscoe Village Burger Fest

Roscoe Village Burger Fest is quite literally one of my favorite Chicago’s fest. In my opinion, it’s a must add to your Chicago Bucket List. Over a dozen local restaurants participating, 2 stages of live music, arts & crafts, Kids Zone. It’s on Friday, July 15, 2022 thru Sun, July 17, 2022 this year. 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!

Enjoy Happy Hour on the patio at Fiya

This is a Mediterranean restaurant located in Andersonville, inspired by Israeli neighborhood spots. They have amazing homemade pita and shakshuka. They are also recently included in the Michelin Guide!

Check out the re-opening of Eden

One of my favorite restaurants in Chicago did not make it through the pandemic, but now they are reopening in Avondale! They will serve breakfast and lunch starting June 6, bar and bites and dinner starting June 22. The best part of Eden is that they have an onsite greenhouse to grow their own ingredients!

Rent a boat with friends for a river cruise

My friends and I do this every summer! 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 a 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 and splash area and Pier 31 Restaurant has live music, food, and drinks.

Play a round of Mini Golf at Diversey Harbor

Small but cute mini golf that isn’t super expensive. It’s walkable to the lakefront and a fun family things to do.

Go to the Sheffield Garden Walk

I love this Lincoln Park street festival! It’s been around for many, many years. It used to be a real party scene and now they have added lots of other things to do for the entire family. They have self-guided garden tours, live music, kids area, local food vendors and more! We even went one year as a family and they had a full petting zoo for the kids!

Sheffield Garden Walk on my Chicago summer bucketlist.

Have a picnic in the park

Here are a few places you can grab food and set up in a park.

-Love South Pond area in Lincoln Park. (Pick up a @ranallislincolnpark to-go)

-Pick up lunch at Foxtrot and then go to Wicker Park

-Order to go from Cafe Selmarie and head to Winnemac Park

-Take out from Piccolo Mondo and picnic at Promontory Park at Burnham Park

Farmers markets are the best in Chicago. Add it to your bucketlist

Check out the new Bronzeville Winery

A space full of art, wine, food, and music and they have a Live DJ Friday – Sunday. The food looks amazing and the space is stunning! I can’t wait to visit!

Have a date night at the Millennium Park Concert Series

Free outdoor concerts, bring a blanket and a picnic, or buy from the concessions stands. Bonus is that there are bathrooms on site!

Attend Windy City Smokeout

Happening on 8/4th-7th and Willie Nelson, Tim McGraw, Miranda Lambert and more are all performing! BBQ from all over the country and local places like Bub City, Green Street Smoked Meats, Lillie’s Q, Smoque. It’s so much fun! Tickets are now on sale and Thursday 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 51st Annual Pride Parade

This is one of the best days in Chicago! It Starts at noon on 6/26 and begins at Montrose and Broadway in Uptown. Best viewing Boystown section of North Halsted, between Belmont and Grace. For a less crowded spot, try Broadway between Belmont and Diversey

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 Chicago guides her3 Day Chicago Summer Itinerary!


%d bloggers like this: