Chicago Seasonal Events

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. ✔️ …More

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. ✔️...

4 to 8 hours Free Cancellation
4.3 (20)
from
$150
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

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
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

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
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

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
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, …More

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
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

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
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

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

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

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
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 …More

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...

4 hours
from
$425

Frequently Asked Questions

These answers are based on answers previously given to Key West Private Charters customers' questions.

Recent tour reviews
Activity name

Chicago Tours
Attractions
Guides
Calendar