The Ultimate Chicago Summer Activities Guide: 21 Unforgettable Things to Do

It’s almost that time again: those 3 (maybe 4) sweet months of warmth and sunshine that Chicago gets every summer. They make it possible to get outside and enjoy everything the city has to offer — they also make it worth dealing with the miserable winter months. Here are 21 of my favorite Chicago summer activities that will put you in the summer spirit.

Like Kanye West once said… “Summertime Chi, ahhh. This is the good life.”

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Last updated: 29 December 2022

Best Chicago summer activities

Rent a Divvy and bike down Lake Shore Drive

Divvy is Chicago’s bike share program. You download an app, scan a QR code to unlock the bike, and can ride around the city to your heart’s content. A single trip under 30 minutes is $3.30, while a whole day’s worth of bike rides costs $15. It’s a great way to see the city on a nice day, especially if you’re a tourist wanting to hit all the classic tourist spots.

If you’re in Chicago over Memorial Day weekend, Bike the Drive is a fun event to join. Lake Shore Drive is shut down to cars and opens up for over 20,000 cyclists. (Because of COVID-19, Bike the Drive 2021 is happening in the fall instead of in May.)

Explore a park

The city is filled to the brim with parks, playgrounds, and grassy areas to explore. As soon as it gets warm (or even above freezing), having a picnic or playing with your dog in the park are some of the many quintessential Chicago summer activities. Here are some popular ones:

• Lincoln Park (and Lincoln Park Zoo)
• Maggie Daley Park
• Millennium Park
• Grant Park

Go to the beach

Nowhere else in the US will you find such nice beaches so close to downtown. North Avenue Beach and Oak Street Beach are prime spots to play some volleyball, get some drinks, and splash around in Lake Michigan. You’ll also find vendors walking around and selling ice cream and hot dogs — no ketchup, of course.

Get a beer at Navy Pier

Other than being swarmed with tourists most of the time, Navy Pier is actually pretty cool. They have a beer garden where you can sit outside, listen to live music, and watch the boats around the pier. Once you’ve finished your drink, you can grab some food at one of the many restaurants or take a ride on the 200-foot-tall Ferris wheel.

Walk, run, or cycle the 606

The 606 is an elevated trail and greenway that runs east to west throughout the city. It crosses the Wicker Park, Bucktown, Humboldt Park, and Logan Square neighborhoods, letting you see a lot of the city in one fell swoop.

Attend Lollapalooza…

… or one of the many other music festivals held in Chicago. Lollapalooza is the largest and most genre-diverse festival you’ll find. It’s held every year in Grant Park, right in the heart of downtown. Some other popular Chicago music festivals include:

• Spring Awakening: Strictly EDM
• North Coast: EDM, rock, and jam-band
• Pitchfork: Hipster & independent
• Riot Fest: punk, rock, and alternative

Go out for rooftop drinks

There’s nothing better than enjoying some rooftop cocktails on a summer afternoon. Chicago has tonsss of tall buildings, and thus, tons of wonderful rooftop bars and lounges. You can find all kinds of different vibes, from classy date night lounges to rowdy gameday pubs. Here is a (relatively short) list of my faves:

• Cindy’s at the Chicago Athletic Association Hotel
• Cerise at the Virgin Hotel
• Devereaux
• Offshore
• The J. Parker
• Utopian Tailgate
• I|O at the Godfrey Hotel
• LH Rooftop at the London House Hotel

Have brunch, lunch, or dinner on a patio

Alfresco dining is the move come summertime. Brunching is something I recommend year-round, but we can all agree that it’s made infinitely better when you can sit outside on a nice day. Here are some restaurants with fun patios or outdoor spaces (and good food!):

• Small Cheval
• Siena Tavern
• Happy Camper
• Beatnik on the River
• 90 Miles Cuban Cafe
• Summer House Santa Monica

Attend a free event at Millennium Park

Millennium Park is a public park in the Loop neighborhood in downtown Chicago. In it, you’ll find the iconic Bean (aka the Cloud Gate), the Crown Fountain, the Lurie Garden, and lots of grassy space. There are free, public events held at Millennium Park throughout the summer. You can attend the Summer Film Series, listen to some live music, or take part in a workout class.

Taste of Chicago & Taste of Polonia

Tase of Chicago is the world’s largest free admission outdoor food festival. It’s held every year in July at Grant Park. You’ll find every kind of cuisine you could possibly want, including traditionally Chicagoan foods like deep dish pizza and Italian beef. There’s also live music, artists, and dance performances to keep you entertained while you eat.

Taste of Polonia is like Taste of Chicago’s Polish cousin. The Polish community in Chicago is massive, so you’ll find lots of authentic food, drinks, and performances here. Taste of Polonia is held every year over Labor Day weekend.

Attend a neighborhood festival

Clearly, Chicago is big on festivals. In addition to the large city-wide festivals I’ve already mentioned, many neighborhoods hold their own festivals or street fairs as well. Here are a few examples:

• Do Division
• West Fest
• Fiesta del Sol in Pilsen
• Northalsted Market Days

Ride the Seadog at Navy Pier

I’ve probably done this boat ride at least five times and it hasn’t gotten old. The Seadog is a fast-paced jet boat tour that kicks off at Navy Pier. You’ll get good views of the city from the water and the guides are always entertaining and insightful. This is a great ride to go on right at dusk so that you’ll see the skyline when it starts to light up.

Local tip: Google “Seadog coupons” before you buy your tickets. There’s often some kind of special deal going on to save some money!

Take an architectural boat tour

Continuing on with the boat theme, an architectural boat tour is a must-do Chicago summer activity. You’ll cruise down the Chicago River, look at a bunch of cool bridges and buildings, and learn about the city’s history. Most of the boats also have a bar on board, meaning you can booze while you cruise. Win-win!

Kayak the Chicago River

If you’re feeling a bit more athletic, kayaking down the Chicago River is a great way to see the city from a new angle. There are several different businesses that you can rent your kayak from. Prices start from about $30 an hour or $90 for the whole day if you’re renting individually. There’s also the option to take kayaking or paddleboarding tours — architectural, sunset, fireworks, you name it.

Watch fireworks

Speaking of fireworks, summer in Chicago is a great time to see some. From Memorial Day to Labor Day, you can catch a fireworks show twice a week (Wednesdays and Saturdays) at Navy Pier. Take a boat ride or have a beer during these fireworks and kill two birds with one stone!

Walk along the riverfront

Chicago’s riverfront is gorgeous. On a sunny day, take a stroll down the newly-renovated Chicago Riverwalk. There is tons of outdoor space to sit and lounge, as well as a plethora of outdoor restaurants and bars for when you get peckish. Here are some goodies:

• City Winery
• Chicago Brewhouse
• Island Party Hut Tiki Bar & Grill

Take a brewery tour

See where your beer is made, then drink it. A brewery tour is a super-fun way to support local businesses and learn about their histories. After your tour, you’ll get to sample the very products you just watched being made. Some of the best include:

• Goose Island
• Lagunitas
• Revolution Brewing

Pride in the Park

June is Pride month throughout the USA, which brings parades, festivals, and plenty of fun parties. Chicago is no exception, with Pride in the Park being held every year at Grant Park. You’ll find food and drink vendors, drag shows, live entertainment, music, and lots of glitter.

Outdoor museum events

Need a little bit of culture in your life? Try attending one of the many outdoor events held by Chicago’s best museums. You can listen to some music, eat some finger foods, and feel fancy while supporting the arts. Here are a couple of options:

• Jazzin’ at the Shedd: Live jazz, amazing views of the Chicago skyline, and open access to the Shedd Aquarium’s exhibits
• Tuesdays on the Terrace: Free outdoor jazz concerts put on by the Museum of Contemporary Art

Go to a Cubs game

Attending a baseball game is the perfect way to spend a summer morning or afternoon. Round up your friends, buy a bunch of cheap beers, and eat your fill of disgustingly delicious stadium food (because we all know baseball is actually really boring).

Visit the Baháʼí House of Worship in Wilmette

Not quite in Chicago, but cool nonetheless. The Baháʼí House of Worship is the second-ever temple constructed for people of Baháʼí faith. A new religion, Baháʼí teaches the “essential worth of all religions and the unity of all people.” The temple is open to the public and can be used as a devotional space for any faith. About 20 minutes away from Chicago, the House of Worship and its beautiful gardens are a nice way to escape the city and get a bit of relaxation.

Book a tour in Chicago

Hopefully this list of Chicago summer activities has gotten you ready for the upcoming summer months! They’ll be here before we know it.

If you’re planning on being in the Windy City during the winter months, don’t fret. Check out my guide to winter activities here.

xoxo Niki

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