Top Chicago Holiday & Seasonal Tours

Chicago Holiday Lights Trolley and Christmas Market Tour

• 27 reviews
• Celebrate the holidays in style during this 90-minute excursion, featuring a trolley tour of Christmas lights at some of Chicago's most famous sights, followed by a shopping trip to the German-themed Christkindlmarket. See Lincoln Park, Daley Plaza and Michigan Avenue adorned with lights for the holiday season. Then find something for the important people on your list at the Christkindlmarket, a German-tinged Christmas offering unique gifts and fun-filled activities for the whole family.
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Chicago Holiday Stroll and Food Tour

• 3 reviews
• 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.
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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.
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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.
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Chicago Fireworks Viewing by Segway

• 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.
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Chicago Holiday Lights Tour by Segway

• 1 review
• 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. Numbers are limited to eight for a small-group experience.
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2.5-Hour Chicago Winter Holiday Walking Tour With Drinks

• Celebrate the holidays in Chicago on a special 2.5-hour walking tour that serves up the Windy City's history with drinks and festive decorations. Wear your warm winter clothing for a tour that spends half the time indoors at landmark spots like the Marshall Field’s Department Store in addition to some time outdoors. Your guide shares commentary about the Daley family and Chicago's mayors, Christmas traditions in the city, and other Chicago lore as you stroll through downtown and pop into two establishments for drinks (optional and at own expense).
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Chicago New Year's Eve Luxury Dinner Cruise

• Board a luxury yacht for a 3-hour dinner cruise on New Year's Eve in Chicago. Choose to be seated in the rooftop lounge or explore the well-appointed ship before sitting down for a 3-course, gourmet meal. Relax with tea and coffee while taking in views of the skyline or dancing to the onboard DJ.
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Chicago New Year's Eve Dinner Cruise with Buffet

• Celebrate New Year’s Eve in Chicago with a 3-hour dinner cruise on Lake Michigan, an evening of dining, dancing, and spectacular views. You’ll set sail from Navy Pier aboard a luxurious cruiser, enjoy a freshly-prepared buffet dinner and dessert bar, then get the party started with a top Chicago DJ. This 3-hour New Year’s Eve cruise includes dinner, entertainment, and a Champagne toast at midnight, with the option to upgrade for a private table and open-bar access.
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Fright Hike: Halloween Edition Chicago 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.
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Moonlit Cemetery Tour - Oakwood 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.
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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.
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Chicago Holiday Lights Tour

• 10 reviews
• Take in the best of Chicago's downtown holiday lights on this 1.5-hour tour. Snuggle up in a heated motor coach for a ride past the best displays, including a stop at the German Christkindlmarket in Daley Plaza for some shopping and snacks.
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