Menu

This Chicago bucket list for first time visitors has the warm weather in mind. Architecture tours are even better when you're basking in sunshine on a boat along Lake Michigan. Free concerts are as good as they get when held under open skies and stars. And quintessential museums and attractions like Art Institute and The Ledge are required for your first go around in Chicago — you can't miss those no matter what time of year. Check off all these Chicago classics with this guide.

These are the 10 things you can't leave Chicago this summer without doing.

 

❏ Architecture Tours

Shoreline Sightseeing

The Chicago Architecture Foundation’s wildly popular tours include river cruises with views of more than 50 architecturally significant buildings, 90-minute walking tours of must-see buildings, architectural highlights by bus and many others. Wendella Sightseeing Boats and Shoreline Sightseeing Company also offer architecture boat tours.

 

❏ Millennium Park

Millennium Park

Millennium Park, one of the state’s most popular tourist attractions features larger-than-life public art (including Cloud Gate, site of the most Chicago selfies each year); the Frank Gehry-designed Jay Pritzker Pavilion, featuring free concerts all summer; Crown Fountain; and the all-seasons beauty Lurie Garden.

 

❏ Navy Pier

Fireworks at Navy Pier Chicago

You can’t truly experience Chicago without a trip to Navy Pier. This 50-acre playground of entertainment, museums, activities and shops is the perfect place for a family outing. Take
a spin on the taller, faster Centennial Wheel, which was upgraded in 2016, and dine at exciting new restaurant additions like Tiny Tavern and The Original Rainbow Cone.

 

❏ Chicago Beaches & Lakefront Trail

Oak Street Beach

Hit the Lakefront Trail to run, walk, bike or rollerblade with the blue waters of Lake Michigan on one side and the city’s renowned skyline on the other. Along the way, stop and relax on one of Chicago’s numerous swimming beaches, like the ones at Oak Street and North Avenue.

 

❏ Skydeck Chicago

Skydeck at Willis Tower

The 103-floor elevator ride to the Willis Tower Skydeck has always been an essential Chicago experience, but the addition of the The Ledge has made it even more thrilling. These glass cubes jut four feet from the building, giving you hair-raising views of the city below and up to four states on a clear day.

 

❏ Art Institute of Chicago

Art Institute of Chicago

No trip to Chicago is complete without a stroll through the storied halls of the Art Institute of Chicago. Explore more than 30,000 works of art, including Chagall’s American Windows, contemporary works by Andy Warhol, Edward Hopper’s Nighthawks and, of course, the towering pointillist masterpiece A Sunday on La Grande Jatte by George Seurat.

 

❏ Shedd Aquarium

Shedd Aquarium Chicago

This white marble temple to aquatic life opened in 1930 and is one of the
largest aquariums in the United States, with 32,000 animals from 1,500 species. Photo ops abound at the Shedd Aquarium, from the playful Penguin Encounter to the ornate Beaux-Arts architecture.

 

❏ Wrigley Field

Wrigley Field Chicago

At Wrigley Field, root for the home team — and reigning World Series champions, 108 years in the making — at America’s second-oldest Major League Baseball stadium, surrounded by the vibrant (and Chicago Cubs-crazy) North Side neighborhood of Wrigleyville.

 

❏ Buckingham Fountain

Chicago Ale Fest

This beautiful landmark fountain located in Grant Park presents nightly colorful light-and-music shows from spring through fall. Buckingham Fountain is one of the largest water fountains in the world.

 

❏ The Magnificent Mile

The Magnificent Mile

Take a stroll along Michigan Avenue, the grand main boulevard of this bustling shopping district. Here you’ll find leading designer boutiques (think Gucci), flagship stores like Ralph Lauren and upscale shopping centers, including 900 North Michigan Shops. The Magnificent Mile is also home to some of the best restaurants and entertainment in the city.

 

Plan your trip around the Chicago festival calendar for even more fun! Street fests set up all summer long, on every weekend and across every neighborhood. And from Lollapalooza to Taste of Chicago, the downtown mega festivals are even bigger reasons to spend your summer here.

Featured Partners

Book A Trip

More Chicago Itineraries
Spend a Weekend in the Chicago Loop
Experience some of the best attractions, theater,...
Sightseeing along the L Train
Chicago has an excellent public transportation...
Chicago Sightseeing
Whether you are planning a Chicago travel...
1 Day Downtown Chicago
With just one day to explore downtown Chicago, go...
Been Here? Do this in 2017
So you've been to Chicago. You LOVE Chicago....
First Timer's Guide to Chicago
First-time visitors are always amazed by...
Bucket Lists for Foodies
20 Things to Eat in Chicago
Discover some of the best things to eat in Chicago...
Chicago Foodie Checklist
Thinking about Chicago's place in the food...
Classic Chicago Food
A guide to Chicago-style hot dogs, deep dish pizza...