Top things to do in Chicago in Summer (Updated November 2026)

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time...
$195

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo...
$99

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are...
$1,180

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the...
$995

This experience is unique for its unmatched flexibility and strong emphasis on group interaction. It’s not bound to a fixed schedule or route, allowing groups...
$20

Private Holiday City Tour
Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal...
$499

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushrooms were...
$20

Private City Tour 6-10ppl
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help...
$770

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to...
$85

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers...
$10

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...
$11

Chicago Small Group City Tour
Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods...
$340

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets....
$30

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the...
$50
![Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]](https://d1qvd96g3tdi20.cloudfront.net/wp-content/uploads/2026/07/da-3.jpg?crop=smart&width=540&format=webp&quality=82)
Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at...
$99

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On...
$158

Chinatown Food Tour
Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore...
$98

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must...
$9

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot....
$325

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city...
$960

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the...
$194

