The Chicago Summer Guide includes 30+ activities and special events to help you make the most of the Chicago Summer.
When the weather is warm, Chicago gloriously comes to life and there are so many ways to spend time outside. The calendar fills up with street festivals and multi-day music fests. Everyone seems to be in a great mood. Locals are always saying that Chicago summers are the best, because they are.
Chicago Summer Guide
Things To Do All Summer
Activities and events that you can enjoy throughout the summer.
Friday Morning Swim Club
A group of Chicago locals started a casual swim club that meets on Fridays during the summer. Participants meet at Lake Michigan (usually Montrose Harbor) around 7am and jump into the lake and swim around for as long as they would like. Once they are done swimming they enjoy some coffee. This was started in 2021 and grew exponentially throughout the summer and will be back for 2022. For details, follow @Andrew_Glatt on Instagram.
Cheer for the Cubs
Cub’s opening day is a sign that summer is on the horizon. Going to a home game at Chicago Landmark Wrigley Field is one of the best ways to spend a warm summer day. If you want a somewhat rowdy afternoon of drinking beer in the sun, opt for bleacher seats.
Movies in the Park
Each summer the Chicago Parks District hosts dozens of movie nights in parks all over the city. The lineup is announced on the Parks District website each spring.
Bike the Lakefront Trail
Chicago’s Lakefront Trail runs for 18 miles along Lake Michigan. You can rent bikes at North Avenue or rent a bike from one of Chicago’s Divvy bike share stations.
Green City Market
Chicago’s most popular farmers market, and one of the best things to do in Chicago, has two locations. The original and biggest market is in Lincoln Park (across from Hotel Lincoln) on Wednesdays and Saturdays from April through October. The West Loop location is open Saturdays from June to October. If you can’t make it to Green City Market, there are other weekend farmers markets in parks throughout Chicago.
Jazzin at the Shedd
The Shedd Aquarium hosts a Wednesday jazz concert series on their terrace with stunning skyline views each summer. And yes, you can tour the aquarium too. Purchase tickets in advance.
Sip Cocktails on a Rooftop
Hotel Lincoln, LondonHouse, The Robey, Time Out Market, Nobu, Cerise, The Gwen, and Aba are all perfect spots for rooftop sips. For a view of the Wednesday and Saturday fireworks, go to Cindy’s. If you want to play games, check out Utopian Tailgate in Old Town.
The Navy Pier Fireworks
Chicago celebrates summer by launching fireworks from Navy Pier every Wednesday and Saturday from Memorial Day through Labor Day. The fireworks are at 9:30 pm on Wednesdays and 10:15 pm on Saturdays. There are many boat tours departing from Navy Pier that offer fireworks cruises.
Explore the Riverwalk
The Chicago Riverwalk runs for 1.25 miles along the Chicago River from Lake Michigan to Lake Street. The Riverwalk provides stunning views of the city and some of its most iconic architecture. Several bars and restaurants are located along the Riverwalk including City Winery. On Wednesdays, you can view Art on the Mart, when art is projected onto Merchandise Mart.
Chicago hosts a wide variety of music festivals. Lollapalooza is a massive four-day festival with many stages and over a hundred bands. Windy City Smokeout is a four-day fest devoted to country music and barbecue. Other fests include Pitchfork, Jazz Fest, Blues Fest, Gospel Fest, and Riot Fest. Jazz Fest, Blues Fest, and Gospel Fest are all free!
Dance in the Parks
The SummerDance series takes place at parks throughout Chicago each summer. Professional dancers give free introductory classes and then people get to practice their new skills to live music. People of all skill levels are invited to these events. The schedule can be found on the chicago.gov website in the spring.
Millennium Park Summer Workouts
This free workout series takes place on Saturdays from Memorial Day through Labor Day.
It seems like every Chicago neighborhood has a street festival during the summer. The Old Town Air Fair, the Sheffield Garden Walk, Do Division, and Wicker Park Fest are just a few on the calendar.
Attend a Food Festival
On a typical summer weekend in Chicago, there are multiple food festivals to choose from. Chicago has Chicago Gourmet, the Taste of Chicago, Rib Fest, Taco Fest, Craft Beer Fest, the Taste of Randolph and more. These festivals are a great opportunity to try bites from a variety of restaurants.
Randolph Street Market
This antique market in the West Loop is the largest urban antique market in the country. You and find an eclectic mix of vintage clothing, jewelry, art, furniture, home decor, and more. The event also has food, drinks, and live music. In 2022, the market will take place on July 30-31 and September 24-25 in the West Loop.
The Lincoln Park Zoo
Admission to this zoo within Lincoln Park is free. The zoo hosts lots of events including Run for the Zoo, a family-friendly 5k road race. The calendar includes some adults only events including Craft Beers at the Zoo and Adults Night Out.
Sip a Negroni Slushy at Parson’s
Parson’s Chicken & Fish has multiple locations, but the Logan Square location has lots of outdoor space and it’s the perfect place to hang out on a summer evening. Parson’s Negroni Slushy is the ideal way to cool down.
Dine al Fresco
Many restaurants in Chicago offer outdoor seating in Chicago. Some popular spots for outdoor dining are Tavern on Rush, Piccolo Sogno, Division Street in Wicker Park, Big Star, Park & Field, Mott St, RPM Seafood, The Dawson, Gibsons Italia, and Beatnik on the River.
Chicago has 28 miles of beaches along Lake Michigan and many of these beaches have volleyball courts. North Avenue Beach has dozens of volleyball courts and court and equipment rental is available through the Chicago Parks District. There are also evening volleyball leagues that are very popular.
Get Out on the Water
There are many different boat rental options for both the Chicago River and Lake Michigan. You can rent stand-up paddleboards, kayaks, and jet-skis from North Avenue Beach. Or you can rent kayaks, small motor boats, or large party boats on the Chicago River. If you want to party, rent a boat and go out to the playpen, a section of Lake Michigan known for partying just off of 700 North Lakeshore Drive.
Shakespeare in the Park
This event series brings free performances of Shakespeare’s work to Chicago parks. The schedule can be found on the ChicagoShakes website.
Millennium Park Summer Music Series
A series of free concerts at the Jay Pritzker Pavilion on Mondays and Thursdays that runs from the end of June through the end of August. The 2022 schedule hasn’t been announced yet but, usually the music series spans genres including jazz, indie rock, blues, salsa, and folk.
Walk or Bike the 606 (Bloomingdales Trail)
The 606 is a 2.7 mile elevated pedestrian path located on a former railway that divides the Wicker Park and Bucktown Neighborhoods.
Explore a Park
Chicago is home to 614 parks, so chances are, you haven’t been to all of them. It’s easy to spend an afternoon in one of the larger parks like Humboldt Park, Grant Park, and Lincoln Park. Some parks even have beaches, outdoor pools, or splash pads.
Ravinia is a large outdoor music venue/park in Highland Park that hosts a summer music series. It is outside the city, but it is easily accessible via the Metro. The full lineup for 2022 has not been announced, but The Black Crows, Esperanza Spaulding, Trombone Shorty, and Bonnie Raitt are on the calendar. Ravinia offers a variety of ticket options; most people opt to picnic on the grass.
Summer Events in Chicago
These are events that take place on a specific day or weekend so mark your calendars.
Chicagohedge is an event when the sunrise and sunset happen to align with the skyline. It happens twice a year, usually around the spring and fall equinoxes. The fall equinox usually falls around September 22 making this event the perfect way to say farewell to summer and hello to fall.
Bike the Drive
On the morning of Bike the Drive, all lanes of traffic, in both directions, on Lake Shore Drive are closed so that cyclists can bike a 30 mile course. The event does require prior registration and tickets. Bike rentals are available. In 2022, the event will take place on September 4.
Pride Fest and the Pride Parade
Pride Fest takes place in Boystown in June the weekend before the Pride Parade. In 2022, Pride Fest will take place June 18-19. This event brings together three stages of live music and performances, food and drink, drag shows, and over 100 art and crafts vendors. The Pride Parade will take place on Sunday, June 26th and will march through parts of Uptown, Lakeview/Boystown, and Lincoln Park.
The annual Auxiliary Board fundraiser for the Shedd Aquarium is attended by a crowd of mostly 20 and 30 somethings and it brings together food and drinks from top restaurants, aquatic performances, dancing on the terrace, and fireworks.
The Air + Water Show
One of the biggest events of the summer, the Air + Water Show is a weekend long event in August that involves jet formation flying (often the Blue Angels) and boat demonstrations. You can see the Air + Water Show from Chicago’s beaches and rooftops near the lakefront.
Renegade Craft Fair
In 2022, the Renegade Craft Fair will host three outdoor markets in Chicago. The first will be in Andersonville on May 21-22, the second will be a pop-up at Pitchfork, and the final outdoor market of the year will be in Wicker Park on September 10-11. Renegade brings together a wide range of artists, makers, and food vendors.
What to Do in Chicago During Fall - cityguidetochicago.com
Sunday 15th of May 2022
[…] of the best times of the year to visit Chicago. The weather is warm without being too hot. Many of Chicago’s summer activities can still be enjoyed in the early fall. When the weather gets cooler, there are opportunities to go […]