6 MIN READ – Summers are fleeting in Chicago, only to give way to our brutal winters, so get out and enjoy the weather while it lasts. Do everything on your summer bucket list, like listening to live music, going on a bike ride, swimming, seeing art at a museum, and visiting the Chicago Loop’s best attractions while it's still warm.
ENJOY LIVE MUSIC
Festival season is thriving in Chicago, with many live concerts to attend. Everything from Broadway Musicals to House music, to Jazz, Chicago has something for all to enjoy.
Monday, August 10 2026, Broadway in Chicago will bring its free annual summer concert to Millenium Park. The one night only event will feature performances from current and upcoming Broadway in Chicago productions, including The Notebook, The Outsiders, along with selections from Dirty Dancing: The Musical. Learn more about the event here.
Thursday, August 27- Sunday, August 30, 2026, The Chicago Department of Cultural Affairs and Special Events hosts the Chicago House Music Festival at the Jay Pritzker Pavilion. This four-day festival celebrates the global impact of Chicago's home-grown genre with free programing, performances, and events at Millenium Park.
Thursday, September 3 - Sunday, September 6, 2026, The Chicago Department of Cultural Affairs and Special Events presents the Chicago Jazz Festival. The 2026 Chicago Jazz Festival will take place in Millenium Park, offering a free opportunity for audiences to experience the full spectrum of jazz, from classic and contemporary to global and experiential. The festival will showcase an all-star lineup of legends, rising stars and hometown icons.
SPEND A DAY AT A MUSEUM
The Loop is home to some of the best museums in the country, as well as smaller, niche museums you’ll only find here. Go to the Museum of Illusions where you can truly experience the impossible. Illusions allow us to see things differently, and they expose a lot about how the brain interprets reality.
Wander through the Art Institute and see historical pieces as well as contemporary works in the modern wing. Are you an Illinois resident? Explore the museum for free with the Art Institute's Free Summer Thursdays from 5-8 p.m. through September 17, 2026. Find out about more Loop museums to check out here.
Be sure to check out other museums and experiences in and around the Loop—everything from specialized spots like the American Writers Museum, Museum of Contemporary Photography, and Museum of Contemporary Art, or fun newbies like Color Factory, and Medieval Torture Museum.
HAVE DRINKS ON A ROOFTOP
Take your night to a whole new level at one of the many Chicago Loop rooftop bars, offering some of the best views in the city. Three top Loop spots are: Boleo, AIRE Rooftop Bar, and Cindy's.
Located 15 stories up inside the Kimpton Gray Hotel, Boleo is the perfect spot to hear the sultry beats of South America paired with bold cocktails and savory Peruvian and Argentinian street snacks.
Another Loop favorite is AIRE Rooftop Bar, located on the 24th floor inside the Hyatt Centric Hotel. This rooftop is the perfect spot for 360 views of the city, and sharable small plates with friends. The fire pit makes it cozy for those breezy summer nights.
Finally, a Loop staple is Cindy's, located in the Chicago Athletic Association Hotel. This is a great spot for stunning views of Millennium Park and Lake Michigan.
Want more? Explore our full rooftop guide here.
RELAX ON THE CHICAGO RIVERWALK
Take a stroll or a bike ride (if it’s not too crowded!), read a book, or simple sit and enjoy the views along the Chicago Riverwalk. Feel as if you're floating as you take in the cityscape along the water. This pathway rests along the bank of the Chicago River for an exclusive view of the Loop’s world-class architecture, with a variety of restaurants, bars, and attractions along the way.
MAGGIE DALEY PARK
Take advantage of the weather and spend some time at Maggie Daley Park. Keep yourself and the kids busy all day with activities like mini golf, wall climbing, and scooter and rollerblade rentals. Also treat yourself to hot dogs and ice cream for the ultimate day out.
VISIT LAKE MICHIGAN
Cool off with a swim, play volleyball or frisbee, listen to music, have a barbeque with friends, or lay out in the sun and relax with your toes in the sand. Check out Ohio Street Beach just north of the Loop, or 12th Street Beach a little to the south. After some fun in the sun and sand, mosey along the Lakefront Trail to the Loop proper for some gorgeous views of the skyline and Millennium Park.
GO FOR A RIDE
Enjoy the weather and get a workout while you’re at it. Enjoy the Loop’s protected bike lanes and the Lakefront Trail for a safe, easy breezy ride. If you don’t own a bike or e-scooter, rent a Divvy for easy access to the city.
