Last Updated September 2, 2020 9/2/2020

11 Fun Things to Do in Chicago

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While the state of Illinois and much of the Midwest is known for its farmland, Chicago stands out as a city of iconic architecture, world-class museums, and deep-dish pizza. There is so much to see and do in this city that you likely need to visit a few times before you understand what it’s all about.

Chicago is a city made up of diverse neighborhoods, local mom & pop shops, and a thriving indie arts scene. Although it only sees a couple of months of hot sunny weather each year, this is the time when locals and tourists take to the beaches of Lake Michigan to soak up some rays and get active in parks and on trails.

How you spend your time in the Windy City often depends on the weather, the season, and where you’re staying. But these are some of the best things to do in Chicago to add to your travel bucket list.

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Hop Onboard an Architecture Cruise
Chicago

Hop Onboard an Architecture Cruise

What Is It? One of the best ways to acquaint yourself with the city and get an overview of the area is to hop on board an architecture cruise.

Why Do It? Knowledgeable tour guides will tell you all about the high-rise buildings that make up the Chicago skyline and their significance to the city.

Good to Know: One option is to book a cruise through Chicago First Lady Cruises, which is a partner of the Chicago Architecture Foundation and offers 90-minute cruises down the historic Chicago River.

Catch a Game at Wrigley Field
Wrigley Field, Chicago

Catch a Game at Wrigley Field

What Is It? Chicago is known as a big sports town, and one way to embrace this energy is to catch a Chicago Cubs baseball game at Wrigley Field.

Why Do It? The stadium’s neighborhood is called Wrigleyville, which comes alive on game days. There are tons of bars in the area to mix and mingle at before and after games, or really any time of the year.

Good to Know: Alternatively, head to Chicago’s Southside to catch a White Sox baseball game at Comiskey Park. Depending on when you visit, you could also get tickets to see the Chicago Bulls basketball team, the Chicago Blackhawks hockey team, or the Chicago Bears football team play instead.

Go Thrift Store Shopping in Bucktown/Wicker Park
Wicker Park row of houses

Go Thrift Store Shopping in Bucktown/Wicker Park

What Is It? Chicago is full of eclectic neighborhoods, so make sure to explore the Bucktown and Wicker Park neighborhoods to find some great local shops.

Why Do It? The intersection of Milwaukee, Damen, and North is filled with lots of interesting local shops, restaurants, and bars to check out while you’re in this area.

Good to Know: Make sure to check out Buffalo Exchange, Crossroads Trading Company, and the Ark Thrift Shop along Milwaukee Avenue.

Explore the Art Institute of Chicago
Art Institute of Chicago

Explore the Art Institute of Chicago

What Is It? The Art Institute of Chicago has been voted the #1 art museum in the world and has many famous masterpieces you are likely familiar with from Monet, Van Gogh, Degas, and many others. 

Why Do It? Even people who only casually appreciate art will love visiting the Art Institute of Chicago.

Good to Know:  You can spend an entire day just exploring this museum if you’re really interested in art. Highlights include the Modern Wing, the Impressionist collection, and the galleries that feature ancient art from Greece, Japan, Africa and other regions.

Jog or Bike the Lakefront Trail
Lakefront Trail, Chicago, Illinois

Jog or Bike the Lakefront Trail

What Is It? The Lakefront Trail is the most scenic place to go for a jog, bike, or even break out those dusty old rollerblades.

Why Do It? This paved and marked trail runs along Lake Michigan and passes by the city’s beaches, which you can stop at to rest, take a dip in the water, or just people-watch. The trail extends for 18.5 miles and is lined with beach volleyball courts, baseball diamonds, tennis courts, and playgrounds.

Good to Know: It’s a great way to get active on your trip to Chicago the way the locals do. The trail also passes by many of the top attractions that you can stop by, like Soldier Field, Lincoln Park Zoo, McCormick Place, and Navy Pier.

Watch a Performance at Second City
Second City

Watch a Performance at Second City

What Is It? Some of the funniest comedians in the world have been trained at Second City, and this comedy establishment offers hilarious shows most days of the week.

Why Do It? Here you can watch famous headlining acts, as well as student performances that feature up-and-coming talent. 

Good to Know: If you plan to stay in Chicago for a while, consider taking a comedy intro class to tap into your own creative side!

Embrace the Tourist Spirit at Navy Pier
Navy Pier, Chicago, Illinois

Embrace the Tourist Spirit at Navy Pier

What Is It? There are lots of restaurants, parks, gardens, shops, and attractions here, and you can’t miss the 150-foot Ferris wheel that operates year-around.

Why Do It? There’s no denying that Navy Pier is a top tourist attraction, but it’s definitely worth checking out if you’ve never been to the city. 

Good to Know: Consider visiting this area at night during the summertime to watch a fireworks display or plan your visit around the Chicago Shakespeare Theater’s performance schedule to watch a show here.

Watch a Concert in Millennium Park
Millennium Park Chicago

Watch a Concert in Millennium Park

What Is It? Millennium Park is a landmark Chicago tourist attraction and most famous for the silver metallic bean, which is actually a sculpture called Cloud Gate.

Why Do It? Chicago can be an expensive city to visit; however, there are lots of free events that you can take advantage of if you know where to look. 

Good to Know: Free outdoor concerts and performances take place at the Jay Pritzker Pavilion in this park in the summer, so bring a blanket and a picnic dinner to enjoy a beautiful evening in the city.

Attend a Local Neighborhood Festival
Chicago Blues Festival

Attend a Local Neighborhood Festival

What Is It? Throughout the spring, summer, and fall, weekend festivals are a way of life in Chicago.

Why Do It? The City of Chicago website, as well as several other entertainment sites, list all of the upcoming festivals, and most of them occur between May and September. Many of the festivals celebrate different ethnicities, foods, local crafts, and live musical acts for locals and visitors to enjoy.

Good to Know: There are also some excellent summer music festivals in the city too, including Lollapalooza, the Chicago Blues Festival, the Spring Awakening Music Festival, and the Pitchfork Music Festival.

Listen to Live Jazz & Blues Music
View of West Loop, Chicago

Listen to Live Jazz & Blues Music

What Is It? Listen to great live music in various venues around town.

Why Do It? Chicago became famous for its jazz and blues scene decades ago and listening to a live performance is a way to immerse yourself in the city’s rich history.

Good to Know: For jazz, head to the Green Mill, which is also known for its slam poetry nights. Other top jazz clubs here are Jazz Showcase and Andy’s Jazz Club & Restaurant. For blues, you can check out Kinston Mines or B.L.U.E.S. for great live shows.

Sip Local Beer at a Craft Brewery
Half Acre Beer Company

Sip Local Beer at a Craft Brewery

What Is It? The craft beer scene has really exploded in Chicago in recent years, and there are some delicious concoctions brewing all around the city.

Why Do It? Visit a tasting room for samples and take a tour of the facilities to learn more about how craft beer is made. Some breweries in the city serve food as well and have outside seating, which is perfect for enjoying a warm day.

Good to Know: Some of the breweries to check out include Goose Island, Revolution Brewing, Half Acre Brewing, and Lagunitas Brewing Company. However, new breweries seem to be popping up all over town on a regular basis.

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