Recent Searches
Clear
When are you traveling?
Select Dates
Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

Ways to Beat the Crowds in Chicago

Ways to Beat the Crowds in Chicago

As a top US destination, Chicago welcomes more than 50 million visitors each year. That said, you can still enjoy a tranquil visit to the Windy City. From exploring by boat to discovering Chicago’s local restaurants and neighborhoods, here’s how to beat the crowds.

Explore the City by Boat

Instead of fighting the crowds of Magnificent Mile, take to the Chicago River or Lake Michigan, from which you can admire the Windy City’s skyscrapers and skyline without the crowds on an open-top boat tour; head out at sunset for the best views. 

Venture Beyond the Loop

The Loop—Chicago’s downtown business district—is home to top attractions such as Millennium Park, the Willis Tower, and the Art Institute, meaning that it’s reliably packed with visitors. Go beyond the Loop’s radius to see how locals live on a neighborhood tour, which tend to cover the heritage architecture of the Prairie District, street art in Pilsen, and the mansions of Wicker Park.

Discover Local Eateries

There’s more to Chicago’s food scene than deep-dish pizza. Enjoy shorter wait times and more diverse cuisine when you venture off-the-beaten-track. Food- and drink-themed neighborhood walks offer a first-hand introduction to many of the city’s less-trafficked culinary haunts, including the coffee shops of Logan Square, Chinatown, and the eateries of River North.

Visit Year-Round

As well as soaring temperatures, summer in Chicago brings peak crowds. For a quieter experience of the city, visit during the shoulder season. Alongside the crisp breezes and golden leaves of fall, you’ll encounter quieter museums and sidewalks. And if you don’t mind a winter-wonderland experience, the Windy City’s snowfall provides a magical backdrop to your exploration. 

Head Underground

One of Chicago’s most surprising attractions is the subterranean Pedway. Located beneath the Loop’s famed skyscrapers, the network lets you slip past crowds and discover a whole new side of the city. Book a guided tour to navigate the underground labyrinth with ease.

Take a Private Tour

Private and small-group tours allow you to the explore the city in a more intimate setting.  Soar over Chicago's iconic skyscrapers in a helicopter tour, or cruise along the lakefront on a private minibus tour customized for your group.

Read More
Filter
Select Dates
Today
Tomorrow
Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

6 Tours and Activities

Sort by: Featured
Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7018
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
More
  • 1 hour
  • Free Cancellation
From
$40.33
From
$40.33

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
330
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
More
  • 30 minutes
  • Free Cancellation
From
$26.16
From
$26.16

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
40
Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
More
  • 45 minutes
  • Free Cancellation
From
$849.00
per group
From
$849.00
per group

Chicago's West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour

star-5
82
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
More
  • 4 hours
  • Free Cancellation
From
$79.99
From
$79.99

Private Chicago Architecture Tour

Private Chicago Architecture Tour

star-5
4
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
More
  • 3 hours
  • Free Cancellation
From
$930.60
per group
From
$930.60
per group

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
3
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
More
  • 3 hours
  • Free Cancellation
From
$482.00
Price varies by group size
From
$482.00
Price varies by group size