Chicago Holiday Tour

Welcome to Chicago: a city that loves to deck the halls while watching “Home Alone” in our Rudolph p.j.s. Join our guides for a stroll in downtown Chicago visiting some of our favorite holiday spots! You will visit the traditional Chicago Christmas tree, scope out good places for ice skating, and discover a few places to grab an indulgent dessert. The guide tell you stories about Chicago being very festive!

The tour will end of the German Christkindlmarket in Daley Plaza where guests can enjoy the festival that will have food, spiced wine, cocoa, and plenty of cheer.

For more fun things to do in Chicago during the holidays, be sure to read out Christmas in Chicago post.


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Some of the sites on the Chicago Holiday Tour:

  • Cultural Center
  • Millennium Park’s Ice skating
  • Chicago’s Christmas Tree
  • Garretts Popcorn
  • Marshall Field’s Holiday Window display
  • Christkindlmarket in Daley Plaza

Reservations: REQUIRED. Click here to reserve. Groups of 9 or more must contact us before booking.

Where: The Chicago Cultural Center: 78 E Washington St, Chicago, IL 60602.  Meet at the South side entrance by the cow statue. The tour will end Daley Plaza at the intersection of Dearborn and Washington

Closet public transportation to Start:  Randolph/Wabash stop for the brown, pink, orange, purple lines OR State/Lake on the red line.

Duration: Tour lasts approx. 1.5 hours. Total walking is just over one mile (1.6km).

When: View our Calendar Tours are on CST time!

Cost: This tour is free to take, and you get to decide what, if anything, the tour was worth when it’s done. A name-your-own-price tour is a tour for anyone’s budget.