The Best Things to Do in Chicago in Summer
Summer is when Chicago becomes the best version of itself. Beaches open, festivals take over entire neighborhoods, free concerts fill Millennium Park, and the Cubs play day games at Wrigley Field with the sun hitting the ivy walls. If you have to pick one season to visit, pick this one.
Beaches and the Lakefront
Lake Michigan's shoreline turns into Chicago's living room from June through September.
The Beaches Worth Claiming Early
North Avenue Beach is the main stage, with volleyball courts, a boathouse, and steady crowds every weekend. Oak Street Beach is smaller, closer to downtown, and ideal for a quick lakefront stop between other plans. Montrose Beach offers more space and a dog-friendly section at the east end. All Chicago public beaches are free and staffed by lifeguards through the season.
Lakefront Trail in Peak Form
The Lakefront Trail runs over 18 miles along the water, and summer is when it runs at full capacity. Rent a Divvy bike, pick up the trail at Navy Pier or North Avenue Beach, and ride north through Lincoln Park. Early mornings and weekday afternoons give you the most room to move.
Festivals That Take Over the City
Chicago runs more summer festivals than any city in the country. Most are free.
The Headliners
Taste of Chicago brings the city's best restaurants to Grant Park in July. The Chicago Blues Festival and Jazz Festival run free performances at Millennium Park. Lollapalooza closes out July and opens August with four days of major-act performances in Grant Park. Neighborhood street festivals, from Wicker Park Fest to Square Roots in Lincoln Square, fill nearly every weekend from late May through September.
Free Music at Millennium Park
The Millennium Park Summer Music Series and Grant Park Music Festival run free evening performances at Jay Pritzker Pavilion throughout the summer. Bring a blanket and settle in on the Great Lawn. No tickets, no reservations.
- June: Chicago Blues Festival, Taste of Randolph, Pride Fest, and Parade
- July: Taste of Chicago, Square Roots, Windy City Smokeout, Lollapalooza (July 30-Aug. 2)
- August: Air and Water Show, Northalsted Market Days, Chicago House Music Festival
- September: Chicago Jazz Festival, Riot Fest
Cubs Baseball at Wrigley Field
Summer is the peak of the Cubs home schedule, and day games at Wrigley Field are a Chicago summer tradition that belongs on every visitor's list.
Day Games in the Sun
Most weekday home games start at 1:20 p.m., putting you back on the street by late afternoon with the entire evening ahead. Arrive early, grab lunch from one of the restaurants on Clark Street, settle in, and soak up a game in one of baseball's most historic ballparks.
The Wrigleyville Scene
The neighborhood around the ballpark runs on its own energy during the summer. Restaurants and bars along Clark and Sheffield keep outdoor seating full from brunch through late night. Gallagher Way, the plaza next to Wrigley Field, hosts events and seasonal programming. Grab gear at the Cubs Team Store or Ivy Shop on your way in.
Outdoor Dining and Rooftop Season
Summer is when Chicago's restaurant and bar scene moves outside.
Patios, Sidewalk Seats and Rooftop Bars
Patio season in Chicago is taken seriously. Restaurants across the West Loop, Wrigleyville, Lincoln Park, and Logan Square expand onto sidewalks and back decks. Rooftop bars like Cindy's, The J. Parker, and LH Rooftop offer skyline views with cocktails. Reservations help at the popular spots, especially on Friday and Saturday evenings.
River and Lakefront Dining
The Chicago Riverwalk lights up in summer with waterfront restaurants, wine bars and casual seating along the south bank of the river. Café Brauer in Lincoln Park and seasonal food vendors along the Lakefront Trail keep you fueled without going far from the water.
Summer Activities Beyond the Obvious
A few summer options fly under the radar but reward anyone who finds them.
Kayaking the Chicago River
Paddling through the downtown river canyon puts you at water level between the skyline's most famous buildings. Guided tours run regularly through the summer, and no prior experience is required for beginner routes.
Outdoor Movies and Shakespeare
The Chicago Park District runs free outdoor film screenings at neighborhood parks on summer evenings. Chicago Shakespeare Theater's Shakes in the City stages free performances in parks across the city through the summer. Check chicagoshakes.com for the current schedule and park locations. Bring a blanket and arrive early for good positioning.
Plan Your Summer Trip
Book hotels early, since summer is peak season. Check the Cubs home schedule and build your dates around a series that interests you. Layer in a festival weekend, a lakefront morning and a neighborhood dinner, and you have a trip that captures everything Chicago does best when the weather cooperates.
Frequently Asked Questions
What is the best month to visit Chicago in the summer?
July offers the most festivals, the warmest weather, and a packed Cubs home schedule. June and August are slightly less crowded.
Are Chicago summer festivals free?
Most are. The Blues Festival, Jazz Festival, Taste of Chicago, and neighborhood street fests are free. Lollapalooza and Riot Fest require tickets.
How hot does Chicago get in summer?
Highs typically range from the low 80s to the low 90s with humidity. Afternoon thunderstorms are common but usually pass quickly.
Can you swim in Lake Michigan?
Yes. Public beaches with lifeguards open in late May or early June and run through Labor Day.
When do Cubs day games start?
Most weekday games start at 1:20 p.m. CT. Weekend start times vary. Check the Cubs schedule for specific game times.
What should you pack for a Chicago summer trip?
Sunscreen, a refillable water bottle, comfortable walking shoes, and a light layer for evening lakefront breezes.