Top Chicago Holiday & Seasonal Tours

Q: Which Chicago Holiday & Seasonal Tours have Instant Confirmation?

Chicago Holiday & Seasonal Tours with Instant Confirmation include: Chicago Architecture River Cruise Chicago Architecture Center River Cruise aboard First Lady Chicago River 90-Minute Architecture Boat Tour Historical and Architectural Chicago Fireboat River & Lake Cruise Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals View all Tours with Instant Confirmation →

Q: I need a ride! Which Chicago Holiday & Seasonal Tours have Hotel Pickup?

No problem. These Chicago Holiday & Seasonal Tours include Hotel Pickup: Chicago City Private Tours Private Holiday City Tour View all Tours with Hotel Pickup →

Q: Got any more Chicago trip ideas?

We sure do. Check out our curated lists of hand-picked Chicago Tours. Top 10 Chicago 2026 Senior-friendly tours Chicago The best tours and activities for culture lovers in Chicago Top Day Trips from Chicago Things to do in Chicago this summer View all Chicago Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Chicago?

Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are: Chicago Luxury & Special Occasions Chicago Luxury Tours Chicago Tours & Sightseeing Chicago Cruises, Sailing & Water Tours Chicago Boat Tours View all tour styles in Chicago →

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 …More

4.9 (16,679)

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...

60 to 75 minutes Free Cancellation

4.9 (16,679)

from
$39

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 …More

5.0 (7,624)

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...

1 hour 30 minutes

5.0 (7,624)

from
$57

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 professional …More

4.9 (1,958)

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 professional...

1 hour 30 minutes Free Cancellation

4.9 (1,958)

from
$37

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 …More

4.9 (492)

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...

2 hours Free Cancellation

4.9 (492)

from
$39

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into …More

4.9 (207)

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into...

2 hours Free Cancellation

4.9 (207)

from
$40

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 …More

5.0 (141)

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...

2 hours Free Cancellation

5.0 (141)

from
$35

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

4.9 (115)

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 corner of...

1 to 2 hours

4.9 (115)

from
$42

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 Holiday Hike, a 3-hour guided …More

5.0 (77)

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 Holiday Hike, a 3-hour guided...

3 hours Free Cancellation

5.0 (77)

from
$85

The Christmas Tree Crawl Experience Chicago at the Holidays

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and …More

4.9 (44)

The Christmas Tree Crawl Experience Chicago at the Holidays

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and...

2 hours Free Cancellation

4.9 (44)

from
$35

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 …More

4.8 (41)

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...

2 to 8 hours Hotel pickup offered Free Cancellation

4.8 (41)

from
$199

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 …More

5.0 (28)

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...

90 to 105 minutes Free Cancellation

5.0 (28)

from
$35

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 …More

5.0 (27)

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...

1 hour 30 minutes Free Cancellation

5.0 (27)

from
$75

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 genocides. This immersive experience …More

5.0 (26)

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 genocides. This immersive experience...

1 to 2 hours Free Cancellation

5.0 (26)

from
$12

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 …More

5.0 (5)

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...

2 hours Free Cancellation

5.0 (5)

from
$45

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

4.8 (5)

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...

2 hours Free Cancellation

4.8 (5)

from
$75

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, …More

5.0 (4)

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,...

Free Cancellation

5.0 (4)

from
$55

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 …More

5.0 (3)

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...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$499

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 …More

5.0 (2)

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...

1 hour Free Cancellation

5.0 (2)

from
$105

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 …More

5.0 (1)

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...

2 hours Free Cancellation

5.0 (1)

from
$205

Spanish Paella Cooking Class in Chicago (Includes 3-Course Meal)

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you through …More

5.0 (1)

Spanish Paella Cooking Class in Chicago (Includes 3-Course Meal)

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you through...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$110

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Chicago Holiday & Seasonal Tours?

What are the best kid-friendly options for Chicago Holiday & Seasonal Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Holiday & Seasonal Tours are:

View all kid-friendly Tours →

Which Chicago Holiday & Seasonal Tours have Instant Confirmation?

Which Chicago Holiday & Seasonal Tours have Free Cancellation?

Chicago Holiday & Seasonal Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Chicago Holiday & Seasonal Tours have Hotel Pickup?

Got any more Chicago trip ideas?

What are the most popular styles of Tours and Activities in Chicago?