Chicago Seasonal Events

31 Results
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

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
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 …More

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...

3 hours Free Cancellation
4.6 (96)
from
$89
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
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
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
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

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
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

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
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
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
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

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