Chicago Seasonal

Explore the best seasonal tours in Chicago, including river cruises, lake cruises, and night tours. Discover Chicago's architecture, skyline, and dark history.

No tours match these filters.

2-Hour Chicago Wine and Cheese Cruise

2-Hour Chicago Wine and Cheese Cruise

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago Riv

★ 4.2 (6)
From $75.00 USD
Chicago Architecture Center Exhibits Admission

Chicago Architecture Center Exhibits Admission

The Chicago Architecture Center (CAC) was founded in 1966 as the Chicago Architecture Foundation to save the historic Glessner House. Since then, the CAC has gr

★ 4.4 (83)
From $15.00 USD
Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chi

★ 4.9 (7641)
From $57.00 USD
Chicago Architecture River Cruise

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of th

★ 4.8 (17211)
From $39.00 USD
Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming ma

★ 5.0 (142)
From $35.00 USD
Chicago Bears Football Game at Soldier Field

Chicago Bears Football Game at Soldier Field

One of the two remaining founding members of the NFL, dating back to 1920, the Chicago Bears are the epitomise NFL history. For an experience filled with tradit

From $425.42 USD
Chicago By Night River and Lake Cruise

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buck

★ 4.5 (468)
From $50.00 USD
Chicago City Private Tours

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable e

★ 4.6 (38)
From $199.00 USD
Chicago City Tours See It All No Time Wasted

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic

★ 3.8 (21)
From $150.00 USD
Chicago Early Skyscraper Walking Tour in the Loop

Chicago Early Skyscraper Walking Tour in the Loop

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden

From $39.00 USD
Chicago Haunted Interior Architecture Ghost Tour

Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn from expert guides wh

★ 5.0 (26)
From $35.00 USD
Chicago Hauntings Original Ghost Walk through Old Chicago

Chicago Hauntings Original Ghost Walk through Old Chicago

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history

★ 5.0 (1)
From $40.00 USD
Chicago Jet Ski Rentals

Chicago Jet Ski Rentals

Rent a premium Yamaha VX jet ski and ride the waves on Lake Michigan with Rev & Ride Adventures. Offering flexible 1 hour ride times, this is a great opportunit

From $170.00 USD
Chicago River 90-Minute Architecture Boat Tour

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a profession

★ 4.8 (1992)
From $37.00 USD
Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chic

★ 5.0 (5)
From $44.99 USD
Chicago Sunset Segway Tour

Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views

★ 4.9 (28)
From $75.00 USD
Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Was

From $496.00 USD
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake M

★ 4.2 (96)
From $24.20 USD
Chicago-Style Holiday Hike: Festive Food and Walking Tour

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holid

★ 4.9 (81)
From $84.99 USD
Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt

Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt

Celebrate the magic of the season this year with Holly Jolly Hunt. Holly Jolly Hunt is an app based scavenger hunt that you can play anywhere of your choosing.

From $20.00 USD
Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water

★ 5.0 (2)
From $105.00 USD
Illinois Holocaust Museum Experience360 Admission

Illinois Holocaust Museum Experience360 Admission

Illinois Holocaust Museum presents Experience360 offers a profound journey through the narratives of survival and resilience during the Holocaust and other geno

★ 5.0 (26)
From $12.00 USD
Lake Michigan Skyline Cruise in Chicago

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy st

★ 4.4 (956)
From $30.00 USD
Original Chicago Prohibition Bus Tour

Original Chicago Prohibition Bus Tour

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, grab a drink and enjoy the

★ 5.0 (5)
From $55.00 USD
Private Christmas Walking Tour in Chicago with Christkindlmarket

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where archite

★ 5.0 (1)
From $1,029.00 USD
Private Holiday City Tour

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 guide! Enjo

★ 5.0 (3)
From $499.00 USD
River North Food Walking Tour

River North Food Walking Tour

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chic

★ 4.6 (98)
From $89.00 USD
Santa Claus Sleigh Ride Cruises on the Chicago River

Santa Claus Sleigh Ride Cruises on the Chicago River

Experience the joy of the holiday season aboard the Santa Claus Sleigh Ride Cruises on the Chicago River. This 75-minute ride offers a unique opportunity to enj

From $20.00 USD
Trickery Chicago Magic Show

Trickery Chicago Magic Show

Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious. Theater is located at 3453 N Halsted Street (near the SE cor

★ 4.9 (116)
From $42.00 USD
Welcome to Chicago: The Essential City Tour with photo stops

Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their histo

★ 5.0 (1)
From $35.00 USD
Winter Fireworks Cruise

Winter Fireworks Cruise

Travel on a piece of history! We travel on the Chicago River seeing the sights after watching the Holiday Fireworks Show. Perfect for Fire enthusiasts, families

★ 5.0 (1)
From $44.30 USD
Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Each dish is crafted with the freshest ingredients and a focus on traditional cooking techniques, resulting in a dining experience that is both authentic and de

★ 5.0 (1)
From $205.27 USD

Reliable & Guaranteed Tickets

Browse trusted tours and experiences in Chicago. Compare options, read ratings, and book with confidence.

Prices and availability are subject to change. Product details are provided by our partners and may be updated without notice.

You may also like

Segway Tours Category

Segway Tours

6 experiences

Self-guided Tours Category

Self-guided Tours

32 experiences

Shopping Tours Category

Shopping Tours

3 experiences

Shore Excursions Category

Shore Excursions

7 experiences