18+ Truly Authentic Chicago Things to Do

We think you’ll agree with us when we say:

There is nothing better than summers in Chicago. It’s why we locals are willing to endure the harsh winters. The city comes alive as soon as Memorial Day hits, with people flocking outdoors to soak up the sun and enjoy the bursts of activity that can be found on every corner.  

With so much to do in Chicago during the summer, it can be hard to know exactly which events, tours, shows and activities to consider during your stay.

After all, you want to make sure you have the quintessential Chicago summer experience, right?

Here’s the thing:

The city isn’t quite as big as it looks, and we’re here to help you navigate all the best things to do this summer so you feel like a native and spend your time (and money!) wisely. Today we’re going to provide 21+ best Chicago summer activities  including events, tours, and much more.

Walk, Bike, or Sail Your Way through Chicago

Chicago is one of the most walkable cities in the country — and it’s during the summer that we really get to find out why. From a leisurely stroll, you’ll be able to check out scenic parks, fascinating art, bustling shopping corridors, lively Chicago festivals, and delicious treats. And for those who prefer to get off their feet, there are lots of other options for getting around, whether by bike or boat.

#1 Hand Over the Hot Dog, Hold the Ketchup

Chicago Things to Do

Source: Chicago Food Planet

Few dishes are as American as the humble hot dog, and few cities have as much of an emotional attachment to it as Chicago does. Get a taste of Chicago dogs and other iconic dishes on a walking food tour, like Chicago Food Planet’s Best in Chow Food Tour.

Their knowledgeable guides will show you some of the most legendary eateries and give you the history of the culinary creations of our fair city. It’s a great way to learn more about Chicago and satisfy all your foodie cravings in one day. If the United States is a melting pot, Chicago’s food scene is certainly one of its most delicious results.

#2 Seek Lush Landscapes in Our Concrete Jungle

Chicago Cloud Gate Bean

Photo Source: Flickr

Chicago owns over 8,000 acres of green spaces, making our parks an integral part of life in the city. Head to Millennium Park to take a pic of the super-Instagrammable “Bean,” also known as Anish Kapoor’s Cloud Gate. Meanwhile, Maggie Daley Park will keep families with children and kids entertained all day with climbing walls, mini golf, and a play garden.

It gets better:

Outside of the Loop, The 606— a converted abandoned rail line — offers 2.7 miles of walking and bike trails, as well as artwork. The Bloomingdale Trail, as it is also known, connects the Wicker Park, Bucktown, Logan Square, and Humboldt Park neighborhoods, making it an ideal way to explore some of Chicago’s hippest and artsiest corridors. The Blue Line Western and Damen stops are the easiest way to get to the park.

Kids will go bananas over Lincoln Park, both a neighborhood and a district park, where they can see chimpanzees at the Lincoln Park Zoo or walk amongst butterflies at The Peggy Notebaert Nature Museum. Lincoln Park is serviced by the Red and Brown Lines on Chicago’s CTA public-transit system.

#3 Merrily Roll Along Chicago on a Bike or Bicycles

Chicago bike tours

Photo Source: Flickr

One of the best things to do in the summer is show off your set of wheels — two wheels, that is. Chicago is a shining example of a bike-friendly city, which is why visitors love hopping on Divvy bikes, Chicago’s bike-sharing program, to get around town.

Want to know the best part?

Every year, the city kicks off the summer season with the Bike the Drive event, where bicycles, tricycles, and the occasional unicycle will take to Lake Shore Drive for five hours of blissful car-free riding. And for the truly bold among us, there is always the World Naked Bike Ride. A liberating experience or the stuff of nightmares? You decide.

#4 Make the Case for Chicago, the Venice of the Midwest

Best Chicago Things to Do guide

Photo Source: Flickr

The city’s waterways connect downtown to both the north and south sides of the city, making it a fascinating route for kayaks, canoes and other paddleboards. If you want to stay on dry land, the Chicago Riverwalk is lined with lively bars, relaxing restaurants, and lots of spaces to idle the afternoon away.

The best way to enjoy Chicago’s waters? Chicago boat tours.

Architecture tours, conducted by Shoreline Sightseeing, are one of the most popular ways to learn about the history of Chicago and take in the city’s amazing landmarks. If you prefer to drink and dine your way around the lake, Spirit Cruises has brunch, lunch, and dinner options that will make your summer sizzle.

Of course, not all tours take place on the water. To learn about more of the best Chicago tours available for locals and tourists, check out our article 15+ Best Chicago Tours: A Comprehensive Guide for Locals & Tourists.  

Insider Tip: Don’t want to splurge on a Chicago boat tour? Here’s a little local secret—you can take a Chicago water taxi all the way to Chinatown for an affordable alternative to river cruises.  Once there, you can learn about this culturally rich neighborhood through its food. Roam around Chinatown Square for a snack, or take a comprehensive look at what Chicago’s Chinese community has to offer with the Chinatown Adventure food and culture walking tour.

From bakeries to dim sum to Szechuan-style dishes, this is one tour that gourmands, foodies and even beginners can really get behind.

#5 Get a Taste of Everything Chicago Offers at Navy Pier

Chicago food tours

Photo Source: Chicago Food Planet

There is no better time to visit Navy Pier, the Midwest’s most popular attraction than during the summer. Featuring over 50 acres of various Chicago attractions, entertainment, and events, the Pier is a perfect way to spend a warm day or a hot night.

Take in the cloudless, sunny skies by riding on the Centennial Wheel. The gondolas provide unobstructed views of Lake Michigan and the Chicago skyline. Head to the Polk Bros Parklawns for live music, outdoor movies, or a great spot to enjoy a picnic with family and friends. Cool off at the IMAX Theatre and enjoy the summer’s biggest blockbusters.

Hungry for more?

Chicago Food Planet’s Navy Pier Signature Food Tour is a great way to experience the best eats and foods the Pier has offer. Guests will get to nosh on some of the most popular offerings while also trying the delicious delights of some of the smaller food artisans. You’ll also learn the impressive history, culture and architecture of Navy Pier that sadly most tourists (and locals) never learn while walking up and down the almost mile-long area.

To learn more about everything Navy Pier has to offer, check out the 27+ Top Chicago Navy Pier Activities + Things to Do guide. 

Discover the Festive Side of Chicago’s Unique Neighborhoods  

#6 Crash a Block Party

Chicago neighborhood street festivals

Photo Source: Northalsted Market Days

The “City of Neighborhoods” is never more evident than in the summer. To get a glimpse of the distinct vibe at each of our 77 Chicago neighborhoods, attend one of the multiple street festivals that invariably pop up during the weekends. A summer staple, Chicago neighborhood street fests feature live local bands, mom & pop booths and stalls, and bites from favorite eateries.

It gets better:

Admission is either free or a small, suggested donation.

Some of the most popular street fests include Do Division and West Fest in the neighborhood of West Town, Northalsted Market Days in the Boystown/Lakeview district, the Silver Room Block Party in Hyde Park, and the Fiesta del Sol in Pilsen.

#7 Find Movie Magic Under the Stars

Chicago Millenium Park concerts

Photo Source: Thrillist

Chicago street fests aren’t the only events that are free and open to the public. Chicago offers an abundance of free programming and events, fit to satisfy our inner bohemian. Film buffs will rejoice with the city’s “Movies in the Park” series. On any given day, you can find a park screening Hollywood classics, kid-friendly entertainment, and box office hits to an attentive crowd.

So:

Be sure to check out the Chicago Park District’s website for exact schedules and lineups. All you need is a blanket and a picnic basket, and you have the perfect Chicago date night all planned out.

#8 Rock Out with Live Music Festivals & Events

Chicago music concerts and festivals

Photo Source: Star Events

Music fans can splurge on ever-popular Lollapalooza, indie darling Pitchfork, or Latin hip Ruido Fest, among other multi-day festivals.

Looking for something a little more affordable?

The great thing about Chicago is that the city also often scores top-notch acts — and you can check them all out without spending a dime. The Millennium Park Summer Serieshas brought world-renowned artists like Aimee Mann, Youssou N’Dour, and Willie Colón to the Pritzker Pavilion Stage. Every Labor Day, the Chicago Jazz Festival also showcases national and international icons of the genre to the Loop.

Finally! We Can Dine and Drink Al Fresco

Chicago best restaurants

Photo Source: Big Star

Come May, June and July, the best seat in any Chicago restaurant will be on a patio.

Get a side of sunshine with your meal with some of our favorite summer food-centric activities with these activities below.

#9 Elevate Your Evening Plans on a Rooftop Bar

Chicago at night

Photo Source: Virgin Hotel Chicago

Toast to some of the most spectacular views of the city by grabbing a cocktail in one of the city’s sky-high lounges. Right on Michigan Avenue Cindy’s offers a breathtaking look at the Lake. The DJs at trendy Cerise (on the rooftop of the Virgin Hotel) will keep you dancing the night away in the Loop.

Ready to venture beyond downtown?

Head north to Lincoln Square’s Gene’s Sausage Shop. A nod to the neighborhood’s German roots, this down-to-earth location serves up delicious beers, brats, and a breezy patio.

#10 Feast on Chicago Festival Food

Chicago street festivals

Photo Source: Star Events

Hit up the weekly Food Truck Fest in Daley Plaza, or keep an eye out for the Food Truck Socials that pop up in some of the city’s hippest neighborhoods. And the Taste of Chicago is a major annual tradition showcasing some of the city’s best bites.

Looking for something a little less crowded?

Smaller food festivals also highlight the vibrant cultures of our communities. Check out Mole de Mayo, which features lucha libre, traditional Mexican dancing, and all the mole you could ever want.

#11 Navigate the Hot Chicago Restaurant Scene

chicago best activities

Source: Chicago Food Planet

Summer is also a great time to explore the city’s culinary center: the West Loop. The foodie neighborhood is where Chicago’s most lauded restaurants sit side-by-side with hidden gems.

Chicago Food Planet’s Gateway to the West Loop Food Tour   Tour takes visitors down world-renowned Randolph Street for a bite of the innovative dishes that have put our dining scene on the map.

Three hours, five full restaurant dishes to eat, one happy mind and belly!

Cool Off with a Nice Chicago Swim

#12 Discover Beaches Away from the Coasts

chicago best beaches

Photo Source: Flickr

For a landlocked city, Chicago has a ton of options for taking a dip when the heat gets too intense. Lake Michigan offers twenty-six miles of shoreline for swim, sand, and sun. If you don’t want to stray too far from the Loop, you can set your towel down at Ohio Street Beach.

That’s not all:

For those who don’t mind heading out a little farther, hit the volleyball courts in North Avenue Beach or look for a quiet spot to read at Rogers Beach.

Want to take a dip with Fido?

Pet lovers can’t get enough of dog-friendly Foster Avenue Beach, where dogs can swim laps in the lake’s cool waters.

#13 Dive into the City’s Pools

chicago best hotels

Photo Source: The Robey Hotel

Not a fan of sand in your pants?

The rooftop pool at Wicker Park’s The Robey is the place to see and be seen, preferably with a refreshing cocktail in your hand. Or, make a friend with a membership to the West Loop’s super-exclusive outpost of the international club Soho House.

If you prefer a family-friendly atmosphere, the Chicago Park District operates close to 50 outdoor pools, open from mid-June to Labor Day.

#14 Run through Massive Sprinklers

chicago events

Photo Source: Flickr

Children — and, let’s face it, most adults too — will have a blast splashing around Crown Fountain in Millennium Park. The multimedia art by Spanish artist Jaume Plensa, almost defies explanation — but it’s one of the most entertaining examples of public art in the city. A pair of glass brick towers looms over a granite pool.

What images are displayed on these towers?

Well, the faces of ordinary Chicagoans. Cute, right? Except nozzles attached to the towers make it look like their mouths are spewing water on passersby below.

Still cute?

Honestly, the cheerful shrieks and giggles from the cheerful crowd mean we don’t mind the fountain’s tongue-in-cheek humor.

Celebrate All Things (Chicago) Americana

Chicago is the rare city that is both cosmopolitan yet also an integral part of the heartland. A Midwestern city through and through, Chicago makes it easy to indulge in some of our country’s greatest traditions.

#15 Take Me, You, Everyone Out to the Ball Game

chicago families

Photo Source: Flickr

Catch a baseball game at historic Wrigley Field or snazzy Guaranteed Rate Field, home of the Chicago Cubs and White Sox, respectively. Better yet, see the city battle it out in the Crosstown Classic, when both teams play up their rivalry in one unforgettable matchup.

Tickets to games can be purchased at the stadium, online, or by calling the box office. Cubs’ fans will be happy to know that the ballpark is only half-block away from the Addison Red Line L stop in Chicago’s popular Wrigleyville neighborhood. Guaranteed Rate Field is also accessible via public transportation. White Sox ticket holders can take the CTA’s Red Line, Green Line or Metra to get to the game.

#16 Learn the Meaning of “Chicago-Style” Deep Dish Pizza

Chicago deep dish pizza

Source: Chicago Food Planet

No summer would be complete without a slice of pie—in  this case, the cheesy kind of pie. Deep-dish pizza is a true Chicago classic and visitors to the city will want to sink their teeth into the real deal.

Wondering where you can get a taste?

Chicago Food Planet’s Second City Classic Food Tour invites guests to a slice of Lou Malnati’s iconic pizza. The popular culinary tour also visits six other mainstays in the Gold Coast and Old Town neighborhoods, a historic corner of our beautiful city that includes the original Playboy Mansion and the world-famous Second City Comedy Club.

We’ll show you why, despite our Second City nickname, Chicago is second to none when it comes to food, history, and architecture.

#17 Chicago Wouldn’t Dare Rain on Your Parade

chicago gay pride festival

Photo Source: Wikipedia

Chicago is also a multicultural city that thrives on the strength of our different communities coming together. Our diversity is on full display during the summer, with dozens of Chicago parades that showcase our beauty, strength, and love of our city.

The season kicks off with Memorial Day Parade, held during the holiday weekend in the Loop. The ceremony starts in Daley Plaza before heading south on State Street.

There’s more:

Celebrate love in all its forms during Pride Parade, held annually on the last Sunday in June in the epicenter of Chicago’s gay culture, the Boystown neighborhood. The South Side’s Bud Biliken Paradeis the largest African-American parade in the country and a perfect way to spend a hot, August afternoon. Some of the parade’s Grand Marshalls have include Chance the Rapper, Chaka Khan, and President Barack Obama.

# 18 Wish America a Happy Birthday

Chicago architecture cruise tours

Photo Source: Odyssey Cruises

Finally, no Chicago summer would be complete without the eye-popping Chicago fireworks show during the Fourth of July. Grab a coveted spot at Navy Pier, fling a towel on the city’s shoreline, or reserve a seat at a high-rise bar.

Bursts of red, white, and blue will wow you with their splendor.

Connect With Chicago Food In Unexpected Ways


Enjoy the Best in Chow Food Tour on TripAdvisor’s #1 Rated Chicago Activity.

Skip the lines & eat iconic Chicago-style dishes in River North and Streeterville.

Offered daily; Includes Chicago-style hot dog, popcorn and deep-dish pizza. 


$57 Adult Tickets (Food Included)
3 Hours; VIP & Child Tickets Available

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