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.

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5-Day Tour of Superior, Huron and Michigan from Chicago

5-Day Tour of Superior, Huron and Michigan from Chicago

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 located in Lake Michigan in t

★ 5.0 (2)
From $1,348.00 USD
Artisan Italian Pasta Class in Chicago (Includes 4-Course Meal)

Artisan Italian Pasta Class in Chicago (Includes 4-Course Meal)

Step into a welcoming kitchen in Chicago for an immersive Italian cooking class hosted through Cozymeal. Limited to 8 guests, this interactive workshop introduc

From $162.00 USD
BYOB Chicago River Guided History Tour

BYOB Chicago River Guided History Tour

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the

★ 5.0 (4)
From $65.00 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 (7083)
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 (17002)
From $39.00 USD
Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architect

★ 4.0 (51)
From $99.00 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 (434)
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 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 (2)
From $35.00 USD
Chicago Pier Fireworks Segway Tour

Chicago Pier Fireworks Segway Tour

See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night while gliding th

★ 4.9 (35)
From $79.92 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 (1896)
From $37.00 USD
Chicago River Cycleboat Cruise

Chicago River Cycleboat Cruise

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite d

★ 5.0 (16)
From $65.00 USD
Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chic

★ 4.1 (213)
From $46.00 USD
Chicago River Guided Ghost Tour

Chicago River Guided Ghost Tour

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and t

★ 5.0 (6)
From $65.00 USD
Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have

★ 4.0 (128)
From $42.00 USD
Chicago River Yoga Walk Tour

Chicago River Yoga Walk Tour

This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga

From $44.00 USD
Chicago Seadog River & Lake Architectural Tour

Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail thr

★ 4.5 (301)
From $41.65 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 Sightseeing River and Lake Cruise

Chicago Sightseeing River and Lake Cruise

Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings an

★ 4.7 (724)
From $46.00 USD
Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board

★ 3.9 (37)
From $42.00 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 Walking Tour: Art Deco Skyscrapers Riverfront

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco

★ 4.9 (102)
From $35.00 USD
Chicago Walking Tour: Must-See Chicago

Chicago Walking Tour: Must-See Chicago

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune To

★ 4.9 (169)
From $35.00 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
Drunk Shakespeare Ticket – Chicago

Drunk Shakespeare Ticket – Chicago

One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!

★ 4.6 (161)
From $29.00 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
Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

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 western shore of Lake Mic

★ 5.0 (2)
From $1,125.00 USD
Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mun

★ 5.0 (51)
From $45.00 USD
Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights.

★ 4.9 (488)
From $47.00 USD
Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)

Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)

Get to grips with Italian pasta in this Florentine-inspired hands-on class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs. C

From $145.00 USD
Lake Michigan 30 Minute Speedboat Ride

Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view

★ 4.1 (360)
From $39.27 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 (950)
From $34.00 USD
Navy Pier Chicago: Private Sailboat Charter with Captain

Navy Pier Chicago: Private Sailboat Charter with Captain

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate a

★ 5.0 (1)
From $1,399.00 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 (4)
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
Tamales and Tacos with Margarita Cooking Class at Su Casa

Tamales and Tacos with Margarita Cooking Class at Su Casa

Immerse yourself in the vibrant flavors of Mexico with a hands-on cooking class at Su Casa Mexican Restaurant. Guided by experienced chefs, participants will le

★ 4.5 (2)
From $59.00 USD
The Devil in the White City: A Haunting History Tour

The Devil in the White City: A Haunting History Tour

We are Chicago's first and best Devil in the White City tour, offering the history, legends and lore surrounding H.H.Holmes, the World's Fair and Victorian Chic

★ 4.5 (17)
From $74.99 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 (111)
From $41.00 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

From $35.00 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

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