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Top Chicago Holiday & Seasonal Tours

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Holiday Hike Chicago-Style: Festive Food & Walking tour

clock 3 hours
  • Get immersed in this Holiday Hike Chicago-Style tour
  • A festive tour where travellers will witness the festivals of Chicago Read more
  • A walking tour through the Millennium Park, Palmer House, the Hilton Historic Lobby, Macy's on State Street and many more places
  • What You'll Do:

  • The tour begins at 130 E Randolph St, Chicago
  • Meet the guide at the Giordano's Pizzeria to taste stuffed pizza also popularly known as deep-dish pizza, a speciality of Chicago
  • Visit Millennium Park which is equipped with an ice-skating rink, where tourists get a chance to glide on ice to their hearts content
  • At Palmer House Hilton Historic Lobby, 17 E Monroe St, Chicago, stop to eat some tasty sweets, a place where the chocolate treats were first discovered
  • Get a chance to see the holiday decor at Macy's on State Street, 111 N State St and then you will be taken to Daley Bicentennial Plaza for shopping
  • Visit the open ampitheatre at Jay Pritzker Pavilion
  • What It Includes:

  • Time taken to cover this trip is approximately 3 hours
  • Food samples are served to the tourists
  • Visit some of the main attractions of Chicago
  • The tourists are accompanied by a local tour guide
  • Holiday Cocoa or Cider are served to travellers as refreshments
  • A moderate level of physical fitness is required to participate in this tour
  • Travellers Talk:

  • The tourists found the tour extremely informative and stated that the guide was friendly and well-behaved
  • They said that the food stops were on desirable joints where they had a lot of fun
  • The tourists loved the company of their guide
  • Is It Right:

  • A trip perfect for all who wish to view and experience the festivities of the Windy City
  • One can take part on this trip with their family and friends
  • Read lessRead more

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

clock 2 hours
  • There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago. Our entertaining guides will get your holiday spirit primed with...Read more

Christmas Eve Plated Dinner Cruise on Lake Michigan

clock 3 hours
  • Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks,...Read more

The Christmas Tree Crawl Experience Chicago at the Holidays

clock 2 hours
  • On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s,...Read more

Chicago’s Festive Lights: A Magical Christmas Journey

clock 2 hours
  • “Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Begin your tour at 875 North Michigan Avenue, formerly known as the John Hancock Center, which is often adorned with holiday decorations and offers spectacular views of the city’s festive lights....Read more

New Year's Eve Plated Dinner Cruise on Lake Michigan

clock 4 hours
  • Set sail on a breathtaking celebration with a Premier Chicago New Year’s Eve Fireworks Dinner Cruise
    on Lake Michigan. Indulge in an unforgettable evening of delicious craft cocktails, plated, chef-prepared
    menus, top-notch service and the best views of the spectacular Chicago fireworks display. Our DJ sets the
    mood while you soak in...Read more

Chicago New Year's Eve Buffet Dinner Cruise on Lake Michigan

clock 3 hours
  • Embark on the ultimate New Year’s Eve celebration with our Signature Dinner Fireworks Dinner Cruise. Come together for unparalleled festivities with dining, dancing, and magnificent skyline views lit up by
    the dazzling fireworks display over Lake Michigan! Enjoy a delicious, chef-prepared buffet and gorgeous views of Chicago’s spectacular...Read more

2-Hour Chicago Holiday Lights Segway Tour

clock 120 to 135 minutes
  • See Chicago all decked out in holiday lights on a Segway sightseeing tour of the Windy City’s sparkling downtown. Get into the holiday spirit as you ride past the bean sculpture and Millennium Park Ice Rink, admire festive window displays at Macy’s (formerly Marshall Fields) and glide under twinkling lights along Michigan Avenue. End your...Read more

Fright Hike: Chicago Halloween Bike Tour

clock 3 hours
  • Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour. Hop on two wheels and follow Bobby’s expert tour guides through some of the most paranormal and frightening spots in the Windy City. This 3-hour guided bicycle tour explores...Read more
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