Best Things To Do In Chicago In The Summer

April 21, 2022

Perhaps because its winters are notoriously tough, there is no shortage of things to do in Chicago in the summer. Locals and visitors alike celebrate the city and the weather, taking to beaches and street festivals, touring iconic architecture or finding a perch to people watch.

Here’s a quick guide to getting the most out of your Chicago summer:

Live Along the Lake

Many of the best things to do in Chicago in the summer involve the Lake.

On a budget? The 18-mile lakefront trail takes you past museums, parks, Navy Pier and more. It percolates with runners, bikers and tourists in warm weather months. A splash in the Crown Fountain and getting up close to the Bean in Millennium Park costs nothing. All of Chicago’s 26 beaches are free.

Dine Outdoors

Big Star in Wicker Park claims to be the most-visited patio in Chicago — and its prime people-watching, Mexican street fare, and focus on bourbon and beer do little to cause doubt. Piccolo Sogno’s tree-shaded patio is a West Loop surprise and the perfect setting for its rustic Italian food. Beatnik on the River dazzles with lush décor and food that draw on Mediterranean and Moroccan influences, not to mention its Chicago River backdrop.

Drink on a Rooftop

No Chicago summer guide would be complete without a few suggested cocktails with a view. There are dozens of rooftop nightspots, but among our favorites are:

  • Cerise: Sitting 26 stories above the Theatre District atop Virgin Hotels Chicago, Cerise bubbles early and late with a decidedly unstuffy vibe.
  • Cindy’s Rooftop: On top of the Chicago Athletic Association Hotel, Cindy’s offers stunning views of Millennium Park and Lake Michigan, as well as a glass atrium indoor lounge in case the weather turns.
  • Utopian Tailgate: Perched above The Second City, Chicago’s famous improv comedy showcase, Utopian Tailgate is an Old Town newcomer bringing all the attitude you’d expect from its location. Play super-sized Jenga, try out a tire swing or grab a cabana.

Among many others to consider are Soho House in West Loop, Lonesome Rose in Logan Square, Whiskey Business in Wicker Park and Homestead on the Roof in West Town.

Fest It Up

Chicago’s love of street festivals isn’t restricted to the summer months. There are hundreds throughout the year, touching every corner of the city. However, our favorites include:

  • June: Chicago Pride Fest; Chicago Blues Festival; Old Town Art Fair; Puerto Rican People’s parade
  • July: Lollapalooza; Taste of Chicago; Wicker Park Fest; Chinatown Summer Fair
  • August: Chicago Air and Water Show; Windy City Smokeout; Uptown Art Week

Tour the Town

You can take walking restaurant tours, public art tours, bike tours and self-guided architecture tours; grab a seat in a sight-seeing, double-decker bus; or take a ride through Roaring ‘20s gangster spots. However, maybe the best views of the city are by water, and to gain a deeper understanding of why Chicagoans are understandably proud of their architecture, a Chicago River architecture cruise should not be missed.

You’re Going to Need More Summers

We haven’t touched on fireworks at Navy Pier, or volleyball at North Avenue Beach, walking the 606, or checking out free workouts or movies in Millennium Park. You’re going to need a home from which to explore the best things to do in Chicago in the summer for years to come.

Reach out to us today to start your rental search.


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