Free cancellation: get a full refund up to 24 hours in advance. Learn more

Top Chicago Holiday & Seasonal Tours

Category
Select Dates
Filter




Clear Filters
Clear Filters

12 Tours and Activities

Sort by:Default


Holiday Hike: Festive Chicago Food and Walking Tour

Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$80.00
From  
$80.00
See Details

Private Navy Pier Fireworks Sail in Chicago

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$445.76
From  
$445.76
See Details

Chicago Helicopter Tour With Holiday Lights

Celebrate the holidays in Chicago with a special scenic helicopter ride that provides a dazzling perspective on the Windy City's top attractions. Depart from a heliport located downtown near the Loop and fly over illuminated landmarks such as Willis Tower (formerly Sears Tower), Navy Pier, Wrigley Field, Lincoln Park Zoo, and Lake Michigan while listening to commentary from your pilot about the history of Chicago. At the heliport, you can enjoy hot chocolate and seasonal treats, history exhibits, and an interactive flight simulator.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
From  
$178.00
From  
$178.00
See Details

30 Minute Chicago Helicopter Tour With Fireworks Show

Get a front row seat to Chicago’s fireworks display during a 25 to 30-minute helicopter ride above the Windy City.  The nighttime tour takes you over Navy Pier, the Loop, and North Side. Listen to in-flight commentary through a provided headset, which also mutes outside noise. Then, fly to Navy Pier and photograph the stunning fireworks from above before returning to the Earth.
  • Duration: 25 to 30 minutes
  • Free Cancellation
  • Duration: 25 to 30 minutes
  • Free Cancellation
From  
$249.00
From  
$249.00
See Details

2 HR Chicago Holiday Lights Segway Tour

Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this 2-hour Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive displays at Macy's department store. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.
  • Duration: 120 to 135 minutes
  • Free Cancellation
  • Duration: 120 to 135 minutes
  • Free Cancellation
From  
$70.40
From  
$70.40
See Details

2 HR Fireworks Segway Tour

Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$65.30
From  
$65.30
See Details

Fright Hike: Chicago Halloween Bike Tour

Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$64.00
From  
$64.00
See Details

Chicago After Dark: Secret Gardens, Live Music, and Fireworks!

See how pretty Chicago is at night on this walking tour. Your guide will bring you through some of the well known and hidden gems in and around the Magnificent Mile, pointing out details you may have missed on your own. The evening ends with a view of the fireworks at Navy Pier from a secret spot only a few have been lucky enough to discover.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$25.00
From  
$25.00
See Details

NEW TO VIATOR

Moonlit Cemetery Tour - Bluff City Cemetery

• Join us on an interesting tour of this historic cemetery. Unlike other tours which just talk constantly, you get to enjoy the peace and quiet of the cemetery and anticipate the experiences that await you. • During the tour you will learn some history about the cemetery and different burial practices of the past. We will teach you how to try and capture paranormal activities on your camera, or camera phone. • included in the price is the use of special equipment for detecting Spirits in the cemetery. • This is small-group tour (20 people max) • The tour lasts 3 hours • Your experienced Spirit Guides will take you on a fascinating Moonlit Tour of the Cemetery. • Afterlife Tours, Inc. is giving a percentage of every ticket sold back to the Cemeteries, to assist in the preservation, and reconstruction, of this historic cemetery.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$50.00
From  
$50.00
See Details

NEW TO VIATOR

Roaring 20's - Prohibition New Year's Eve at Morgan MFG

Come inaugurate the new decade with us at one of the spiffiest joints to pop out The Windy City in recent years. The Roaring 20’s Prohibition New Years Eve at Morgan MFG is the can’t-miss Chicago New Years soiree of the season. Don’t let the name fool you, no coppers are going to pinch anyone for sipping some giggle-water at this shindig. A ravishing night of drinks, dancing, tasty grub, and a midnight champagne toast await you. Sounds pretty peachy-keen, doesn’t it? Then what’re you waiting for? Get those tickets pronto! You’ll only get one chance to start 2020, so do it right. Address: Morgan MFG - 401 N Morgan St, Chicago, IL 6064221+ Event: ID must be shown upon entry. Doors Open: 8:15 PM Ends at: 2:00 AM
  • Duration: 5 hours 45 minutes
  • Duration: 5 hours 45 minutes
From  
$128.50
From  
$128.50
See Details

NEW TO VIATOR

Rock the Yacht: Halloween Midnight Yacht Party Aboard the Spirit of Chicago

Gather round ghouls and goblins, because Saturday, Oct 26th, we’re throwing a pre-Halloween midnight yacht party aboard one of ChiTown’s best-kept secrets, The Spirit of Chicago Yacht. Have a ball and sail with us across The Lake on the hottest Halloween boat party Chicago has going on. Tickets to this event will run out fast! So hurry and secure your spot aboard this incredible yacht.Important information about the event:Dress code is optional! You will NOT BE TURNED AWAY at boarding if you are not in costume.21+ Event: ID must be shown upon boarding.    Boarding: 11:30 PMDeparting: 12:00 AMReturning: 2:00 AM
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
$35.50
From  
$35.50
See Details

NEW TO VIATOR

The Nightmare at Navy Pier Presents: The 5th Annual Haunted Halloween Ball

The Aon Grand Ballroom has once again become haunted, and the only way to get rid of these bad spirits is with a wild night of dancing, drinking, and other lively activity not associated with the undead. Thankfully, they’ve entrusted the party pro’s of ChiTown to take care of business.Doors Open: 8:00PMDoors Close: 2:00AM
  • Duration: 6 hours
  • Duration: 6 hours
From  
$35.50
From  
$35.50
See Details


Book online or call
(888) 651-9785
(888) 651-9785