Best Seasonal & Holiday Activities in Central Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

Filter Seasonal & Holiday Activities in Central Chicago

Chicago: Ghost Bus Tour of Haunted Locations

Join a ghost tour of Chicago established by author and seasoned paranormal researcher Ursula Bielski. Take the bus to intriguing sites, including the Lincoln Park Zoo, John Hancock Building, and more.

$54.00

From

Chicago: Murder Mystery Tour

2 Reviews

Chicago: Murder Mystery Tour

Explore the city and solve a murder on this guided tour through Chicago. Play detective as you discover Chicago's wealthiest neighborhoods, and learn about the real Chicago history along the way.

$35.00

From

Chicago: Spooky Night Cruise on the Chicago River

3 Reviews

Chicago: Spooky Night Cruise on the Chicago River

Listen to stories of Chicago's darker side, including mysterious sightings, creepy haunts, mobsters, and more, as you cruise the Chicago River amidst twilight tales of the city you never knew existed.

$42.00

From

Chicago: Private Yacht Charter

Discover the magic of Chicago's waterways with a private yacht charter. Blend the thrill of the open lake with the iconic skyline of the city as a backdrop.

$1,820.00

~~From $2,275.00~~

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

4 Reviews

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

Celebrate Christmas Eve on a cruise on Lake Michigan aboard the Odyssey. Savor a delicious holiday 3-course plated meal served at your private table with a live onboard DJ.

$184.13

From

Chicago: Summer Fireworks Cruise with 3D Glasses and Music

30 Reviews

Chicago: Summer Fireworks Cruise with 3D Glasses and Music

Enjoy unbeatable views of the Navy Pier fireworks enhanced with commentary 3D glasses, a musical accompaniment, and lively narration on this cruise. Capture photos in front of the Chicago skyline.

$49.00

From

Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

2 Reviews

Bobby's Fright Hike: Halloween Edition Chicago Bike Tour

Join Bobby’s Bike Hike as we unleash our Halloween "Fright" Hike bike tour through the city of Chicago. Professional actors will guide you through the scariest stories of the city, bringing to life the most famous ghosts who still haunt Chicago today.

$54.99

From

Chicago: 360 Chicago Observation Deck Sip and View Ticket

172 Reviews

Chicago: 360 Chicago Observation Deck Sip and View Ticket

Take your cocktail hour to a new level at CloudBar, 1,000 ft above the Magnificent Mile, with a full 360-degree view of Chicago.

$43.50

From

Chicago: Sunset Tour by Open-top Bus with Live Guide

42 Reviews

Chicago: Sunset Tour by Open-top Bus with Live Guide

Experience the Windy City’s dazzling skyscrapers lit up at night. Set off on a panoramic night tour from Navy Pier to the Magnificent Mile, passing by the Chicago Theatre and Buckingham Fountain.

$44.55

~~From $49.50~~

Chicago: 1.5-Hour Lake and River Architecture Cruise

1380 Reviews

Chicago: 1.5-Hour Lake and River Architecture Cruise

Skip the ticket line for Chicago’s only architecture cruise on both Lake Michigan and the Chicago River. Learn about Chicago's internationally-known architecture from expert local guides as you discover the city from riverfront to shoreline.

$44.00

From

Best Seller

Chicago: Museum of Ice Cream Entry Ticket

111 Reviews

Chicago: Museum of Ice Cream Entry Ticket

Enjoy a fully immersive experience at the Museum of Ice Cream, delivering joy and entertainment for the whole family. Savor signature ice cream flavors and sweet treats as you explore the museum.

$49.29

From

Chicago: Self-Guided Audio Walking Tour

3 Reviews

Chicago: Self-Guided Audio Walking Tour

Discover the beautiful city of Chicago on a self-guided tour. See the prettiest spots like Cloud Gate, Millennium Park, Riverwalk, and more while learning the history of the city.

$16.99

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