Top Chicago Seasonal & Special Occasions

Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

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.

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.

The Chicago Winter Photoshoot is a 30 minute photoshoot, capturing the best of the city sights on the Magnificent Mile as your backdrop. PRICING is PER GROUP, not per person. If you sign up as 1 adult this will qualify as payment for your entire group. Gather your nearest and dearest and start the new year out just right, with a fun city photoshoot! We will walk within a few block radius to capture the perfect photos and memories with your significant other, family, and/or friends. If you are planning to propose, let us know and we can help execute your plan. After the photoshoot, the professional photographer will send you all of the unedited photos. You will select 20 photos to be edited and receive as digital prints to treasure as keepsake. This magical winter session will be a fun, festive, and memorable occasion!

Experience the vibrant life of downtown Chicago at its most exciting and beautiful time of year! Visit Macy's on State Street, Palmer House Hilton Historic Lobby, Millennium Park.

Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this 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 department store displays. 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.