BEST Things to Do in Chicago in June 2026 (From a Local!)

Searching for what to do in Chicago this June? Here are the best things to do in Chicago in June 2026 (from a local) – from fun outdoor activities and attractions to the best June 2026 festivals and events.

I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

What to Pack for Chicago in June

For out of town visitors, please note that the weather in Chicago in June is usually warm but the weather can be unpredictable and temperatures can vary greatly from day to day or even hour to hour. Be prepared for both summer and spring temperatures as well as rain. Make sure to pack layers and check the weather right before your visit to know what to expect.

Here are my must pack items if you are visiting Chicago in June for the first time:

• Comfortable walking shoes – Chicago is a very walkable city so you will do a lot of walking
• Reusable water bottle – It can get very hot so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella – It does occasionally rain in June
• Light sweater (and scarf) – For cooler nights and cold air conditioned places
• Waterproof case – For your phone if you plan to go kayaking
• Bathing suit and other beach essentials (if you are planning to spend time at the beach)
• External battery for your phone – it will be hard to find an outlet to recharge your phone’s battery when you are outdoors

If you forget to bring something essential, don’t worry. There are many drugstores located close to the popular tourist attractions if you need to pick something up.

Things to Do in Chicago in June 2026

Below are the top things to do in Chicago in June 2026 including all of the best June 2026 events and festivals.

Listen to Concerts Under The Stars

Enjoy a music concert on a beautiful rooftop with city views. Concerts Under The Stars taking place this June include:

Sinatra Under The Stars at AIRE Rooftop
ABBA Under the Stars at AIRE Rooftop
Bossa Nova Under the Stars at AIRE Rooftop

You can find the full list of Concerts Under The Stars here.

Attend a Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this June include:

A Tribute to Taylor Swift
Tribute to Adele
The Lord of the Rings
Best of Bridgerton on Strings
Tribute to Fleetwood Mac on Strings
Tribute to Bad Bunny (Oak Park)

You can find the full list of candlelight concerts in Chicago here.

Minecraft Experience: Villager Rescue

Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.

Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018

Cost: Prices vary. Click here to purchase tickets.

AirOtic Soirée

AirOtic Soirée is a bold, sensual and provocative cabaret-circus experience returning to Chicago for a full summer run. After sold-out runs across the U.S. and Europe, the internationally acclaimed Airotic Soirée is a show that celebrates desire, sensuality, athletic beauty, and erotic elegance. Airotic Soirée is a blend of erotic cabaret and contemporary circus blending high-level acrobatics, seductive choreography and visual artistry. 21+ with valid ID.

Where: Experience 868, 868 North Franklin Street, Chicago, IL 60610

Cost: Prices vary. Click here to purchase tickets.

Take an Architecture River Cruise

Chicago has amazing architecture and the best way to enjoy it is joining an architecture river cruise.

Take a Lake Cruise

If you enjoy being on the water, a lake cruise is a fun activity whether in the day, around sunset or in the evening. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views especially around sunset and a refreshing cool lake breeze. Lake cruises depart from both Navy Pier or the Michigan Avenue Bridge (DuSable Bridge).

If your time is short, you can do a combination river and lake cruise.

Enjoy the Views at Navy Pier

Navy Pier is a must do if you are visiting Chicago with toddlers or young kids.

Ride the large Ferris wheel (click here to purchase a fast pass ticket and skip the long line) for amazing skyline views.

Other fun attractions at Navy Pier include Flyover in Chicago, an immersive flyover experience, the Chicago Children’s Museum, rides and games and several restaurants, bars and shops.

In addition to Navy Pier’s attractions, visitors in the summer can enjoy free events and programs including Live on the Lake!, an outdoor live music series featuring free live music every weekend in the Navy Pier Beer Garden.

Make sure to come back or stay for the free fireworks every Wednesday and Saturday night.

Watch Free Fireworks at Night

You don’t have to wait until July to see fireworks. If you are looking for a fun thing to do in Chicago at night, Navy Pier puts on a free fireworks show on Wednesday and Saturday nights during the month of June.

While you can watch the fireworks show from Navy Pier, you can also watch the show from various spots along the Lakefront.

Another great option for watching the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.

Hang Out on the Riverwalk

The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars, shops and spots to sit and relax along the way.

Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map of attractions on the Riverwalk here.

Hours: Open daily from 6am to 11pm

Go Kayaking in the River or Lake

A fun way to enjoy city views is to go kayaking in the Chicago River or in Lake Michigan. You can rent a kayak in the Chicago River here and Ohio beach here.

You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.

Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

Enjoy Free Music Concerts at Millennium Park

One of the best things to do in Chicago during a nice summer evening is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

The annual Grant Park Music Festival, the only free outdoor classical-music concert series in the US, starts its summer season on June 10, 2026. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors. You can see the full schedule here.

The free Millennium Park Summer Music Series (Mondays and Thursdays, starting June 15, 2026) features a wide variety of music from established and emerging artists.

Hang Out at the Beach

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan. The most popular beaches are located downtown (Oak Street and North Avenue) but they are also the busiest.

You can check swimming conditions at all Chicago beaches here.