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Top Chicago Seasonal Events

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Chicago Tours

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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 …More

4.9 (16,671)

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 (16,671)
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 (7,611)

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 (7,611)
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 (1,948)

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 (1,948)
from
$37
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 …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
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 …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 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 …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
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 …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
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 …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

Likely to Sell Out
Likely to Sell Out
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
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 architectural landmarks are …More

5.0 (1)

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 architectural landmarks are...

2 hours Free Cancellation
5.0 (1)
from
$469
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 history, …More

5.0 (1)

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 history,...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$35
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, …More

5.0 (1)

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,...

1 hour Free Cancellation
5.0 (1)
from
$44
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 stunning views …More

4.6 (897)

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 stunning views...

30 to 45 minutes Free Cancellation
4.6 (897)
from
$30
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 …More

4.6 (444)

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...

1 hour 30 minutes Free Cancellation
4.6 (444)
from
$50
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 …More

4.4 (88)

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...

15 minutes Free Cancellation
4.4 (88)
from
$24
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 …More

4.4 (81)

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...

45 to 60 minutes Free Cancellation
4.4 (81)
from
$15

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