Summer In Chicago

A Guide To Summer In Chicago

Longer days were meant for sunshine rays.

After hibernating for what seems like an eternity and enduring the springtime tease, the moment we’ve all been waiting for has arrived. Time to trade in the umbrellas and boots for our favorite sunnies! Say goodbye to the unpredictable Chicago spring weather and hello to the warm summer breeze. 

This time of year, the city feels more alive than ever (thanks, Vitamin D) especially with many of the events returning to their full glory for the first time since 2019. Our list of top selections of summer festivals, outside activities and picture-perfect scenery will ensure you soak up every last ray of this glorious season.


It’s not a true Chicago summer until you experience a festival…after all the city serves as home base for some of the largest music and food festivals in the nation. Hear your favorite band perform live at Lollapalooza on July 28 through 31 or take in the electric atmosphere of Pitchfork Music Festival July 15 through 17.

You can savor each bite at the Taste of Chicago July 8 through 10, or celebrate Pride at Chicago’s Pride in the Park on June 25 and 26 to support LGBTQ+ performers, artists and more. On the hunt for unique finds or antiques? Check out Randolph Street Market Festival on July 30 and 31.

Outside of the “big” events, there are so many great neighborhood fests as well that really bring the spirit of the city alive. From Andersonville’s Midsommarfest to Taste of Randolph in the West Loop, explore all the options and offerings here.


For Chicago natives and travelers alike, the Pritzker Pavilion at Millennium Park has something for everyone – the architecture of the dazzling metal stage alone is worth the visit. But the park comes alive in the summer with the free outdoor concerts at the Summer Music Series and by watching blockbusters under the city skyline at the Film Series all season long. 

Looking for something a little more active? Begin your Saturday morning with a yoga or pilates class. The park offers free workouts all season so you can say Namaste before heading out for your summer day.


A picture is worth a thousand words,  right? One of the most Instagrammable spots in the city is opening this July with the launch of Chicago’s Museum of Ice Cream, a sweet adventure fit for all ages. This Willy Wonka-esque immersive experience invites you to play in sprinkle pools, ride on the Chicago Sprink-L line and, of course, eat as many sweet treats as you can.

Aim that iPhone up for the Chicago Air and Water Show in August and capture all the showstopping stunts from pilots and boats out on the lake. (Maverick would approve.) Why not finish the evening with a stroll on the riverwalk to see Art on theMART’s 34 digital projectors on display before heading to the beach to view Navy Pier fireworks to top off the night. Your Instagram grid thanks you in advance.


Of course, there’s plenty to venture out and see in the city but we’ve also got plenty going on under our storied roof with a full slate of summer happenings. In June, our OK Pride series includes specialty workshops, yoga by the fire, socials and more. In partnership with Off-Kilter, each program is designed and inspired by each of Off-Kilter’s verticals; Lifestyle, Fashion, Contemporary Art, Music, Food & Beverage, Queer Culture, and Wellness/Beauty. 

You can also break a sweat with our popular Roller Dance fitness classes or get tuned in for a Sofar Sounds Show in the Stagg Court. Explore the full slate of summer happenings and reserve your spot here.

Vacation or staycation, let us be a part of your summer Chicago adventure. Book your next stay here.