10 of the Best Things to Do in Chicago in the Summertime

chicago in the summertime
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Chicago, the third largest city in America, is a city brimming with fun activities, sights, sounds, and tastes!  In the summer months, June-September, the city comes comes out of hibernation and really makes a splash with boats out on Lake Michigan, people walking the Magnificent Mile, biking along the lakeside, restaurants opening up their patios, and so much more.

Below you’ll find my favorite things to do when its summer in Chicago!


10 Things to Do When it’s Summer in Chicago


1.  Marvel at the City’s Architecture on an Architecture Cruise

By far, one of the coolest and most unique ways to see Chicago is on water.  For more than 25 years the city has been running architecture cruises on the Chicago River, showcasing over 50 unique buildings and skyscrapers, explaining how Chicago became one of the largest cities in America in less than 100 years.  The cruise takes you along different branches of the Chicago River and generally lasts about 1.5 hours.  It’s a great way to spend a sunny afternoon – just don’t forget your sunglasses and sunscreen!


2.  Explore the Art Institute of Chicago

Spending time indoors at the Art Institute of Chicago is the perfect way to spend a rainy summer afternoon.  Most notably famous for housing the most impressionist and post-impressionist artwork outside of the Lourve; the Art Institute of Chicago has been around since 1879, making it one of the oldest (and largest) art museums in the world with over 300,000 pieces of art.  For hours of operation and purchasing tickets ahead of time, click here.


3.  Bike Along Lake Michigan

All around Chicago you can rent “Divvy Bikes” and it’s a great way to see a large part of the city affordably.  My favorite way to use Divvy bikes is by biking along the trail following Lake Michigan, starting near Oak Street Beach and riding north.  There are tons of great areas to stop for photos or even stop for a bite to eat along the way.

Make sure to download the Divvy app so that you can easily see where bikes are available and where to drop you bike back off at.


4.  Learn About the History of Chicago at the Chicago History Museum

Another way to spend a rainy Sunday afternoon is by learning about the history of Chicago at the Chicago History Museum.  One of the best museums in Chicago, you’ll learn about the city’s roots and uprising with displays on Abraham Lincoln, Martin Luther King Jr, and historical events like the great Chicago fire.  You’ll also see some of the great things that have come out of the city (like Plan B), and get to understand what makes Chicago so unique and stand out amongst other American cities.


5.  Walk Along the Chicago Riverwalk

One of the best summer activities is to stroll along the Chicago Riverwalk.  By walking, you can stop by different attractions along the way, and stop for food and drinks whenever you see something good pop up.  Two of my favorite stops along the Chicago River are City Winery – the perfect place to grab a glass of wine and sit on the steps overlooking the river – and Pizzeria Portofino.


6.  Pick Up Goodies from the Lincoln Park Farmers Market

The Lincoln Park Farmers Market is by far, the best farmers market in Chicago.  Held in Lincoln Park near Lake Michigan, this market runs every Saturday from 7 am-1 pm from April to November (although dates can vary each year so make sure to check ahead of time).  They have tons of tasty food stands that serve a plethora of different foods – bagel sandwiches, chicken and waffles, grilled cheese, tacos, and more!  Plus you can buy artisanal goods, cheeses, flowers, and other food items to take away.  (One of my favorite stands at the market is Bushel & Peck’s).


7.  See Cloud Gate in Millennium Park

Probably one of the most recognizable structures in Chicago is Cloud Gate or “The Bean”.  This stainless steel structure was created by Anish Kapoor and placed in the center of Millennium Park in 2006.  It looks like a giant “mirror”, reflecting the clouds and surrounding buildings.

Once you’ve checked out Cloud Gate, make sure to walk around the rest of Millennium Park.  I recommend taking a picnic with you and having yourself an afternoon treat once the sun begins to set.


8.  Watch the Cubs Play at Wrigley Field

An iconic summertime activity, seeing the Chicago Cubs play at Wrigley Field is a once in a lifetime opportunity.  Not only is the field famous for being the oldest National League ballpark, but the location of Wrigley Field is also a major highlight.  Located in Wrigleyville, north of downtown Chicago, this area is full of fun restaurants and bars and is particularly lively on game day.  If you’re going to see the Cubs play, I recommend arriving early and seeing what the neighborhood is all about.  I also recommend lunch or dinner at Happy Camper.


9.  Learn About Chicago’s Sordid Past On the Chicago Gangsters and Ghosts Tours

Chicago has a dark past, riddled with crime and horror.  Not only was the city was home to one of the most notorious gangsters in American history – Al Capone; but Chicago has had some truly horrific incidents happen throughout its early years.  And one of the best ways to learn about the people and events that haunt Chicago’s past is on the Chicago Gangsters and Ghosts outdoor walking tour.  The tour lasts about two hours, where you’ll walk about 1.5 miles through the city recounting the past.  You can check times and book tickets here.


10.  Eat at Restaurant Row in the West Loop

Chicago is home to some of the most incredible restaurants in the world and a lot of them live on Randolph Street, known as “Restaurant Row”, in Chicago’s West Loop neighborhood.  My favorite restaurants on Randolph are Girl & The Goat, Au Cheval, Nobu Chicago, and Little Goat Diner.  Restaurant Row (or the West Loop in general) should be visited at any time during the year, but the reason that it’s particularly fun during the summertime is because most restaurants set up fun outdoor patios and some of the streets close off making them pedestrian only.


If you’re traveling to Chicago and are looking to book a stay and a rental car, these are my favorite resources…


As you can see, Chicago is one of the best cities to visit in the summertime.  If you need more help planning a weekend in Chicago, don’t miss this post.  And if you’re planning to head to Chicago during the winter, there are loads of things to do.  Read about them here!


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Disclosure:  This post may contain affiliate links, meaning I get a commission if you decide to purchase through my link, at no cost to you.


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Kylee is a Neonatal Intensive Care (NICU) nurse passionate about making travel affordable and accessible to nurses. Inspiring nurses to travel both near and far, Kylee began Passports and Preemies in 2017 while volunteering in Skopje, North Macedonia as a way to reach nurses and advocate for the prevention of nurse burnout by traveling. Kylee is the original creator of the “8 Day Vacay” – a vacation geared towards nurses who aim to take advantage of the potentially 8 days off between work weeks with no need to use PTO.

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