Few cities deliver the cheer and excitement of the winter holidays quite like Chicago, Illinois. The fun begins in mid-November and keeps on swinging all the way into the New Year. All of the celebrating can seem overwhelming. Where to begin? What will make the most meaningful memories for my friends and family for the holidays or Christmas in Chicago?

The following holiday attractions are essentials, compiled for you by the expert tour guides at Bobby’s Bike Hike. What’s more, all of these spectacular attractions can be seen or tasted on Bobby’s Holiday Hike Season Sampling Food and Walking Tour. Book your festive adventure today!

10 Can’t-Miss Holiday Attractions in Chicago 

  1. Visit the 60 foot tall Christmas tree in Millennium Park
  2.  Make some figure eights at the McCormick Tribune Ice Rink
  3. Glide across the Maggie Daley Park Ice Skating Ribbon
  4. Stroll through the Christkindlmarket Holiday Market for gifts and holiday tastes
  5. Bite into a traditional German bratwurst at various holiday markets and vendors
  6. Peek the festive and narrative holiday window displays at the original Marshall Field’s
  7. Chicago-style deep-dish pizza always hits the spot with its thick, buttery crust and extra-melty mozzarella cheese
  8. Savor the festive decorations and cocktails at the Palmer House Hotel, a historic building in Chicago
  9. Sample the seasonal and festive local beers of Chicago in decorated local taprooms
  10. Indulge in the original chocolate brownie at Palmer House Hotel for a holiday treat

 

Chicago Holiday Tours with Bobby's Bike Hike

 

 

Visit the 60 foot tall Christmas tree in Millennium Park

This awe-inspiring 60-foot-tall Norway Spruce is strung with over 50,000 multicolored lights. Get your Instagram account ready for this no-filter-required goliath.

Make some figure eights at the McCormick Tribune Ice Rink

This glittering frozen surface is located right below Chicago’s beloved Cloud Gate (maybe you’ve heard it called “The Bean”) and is twice as large as the ice skating rink at Rockefeller Plaza in New York City. Second city, nothin!

 

Glide across the Maggie Daley Park Ice Skating Ribbon

This totally unique winter activity, in tandem with the McCormick Tribune rink, makes Chicago the perfect destination for skaters of all abilities. The skating ribbon creates a full alpine experience and allows for laps twice the length of a standard ice rink.

Stroll through the Christkindlmarket Holiday Market for gifts and holiday tastes

This traditional German Christmas market brings over 50 vendors to Daley Plaza every holiday season. Find the perfect ornament, beer stein, cuckoo clock, or other handcrafted gifts for everyone on your list, all the while sipping on cozy hot apple cider!

Bite into a traditional German bratwurst at various holiday markets and vendors

Originating in Nuremberg, the same city that gave us the first Christkindlmarket, spiced bratwurst on a tasty Kaiser roll has become a local favorite treat throughout the holiday season.

 

Peek the festive and narrative holiday window displays at the original Marshall Field’s

Crowds have been traveling from far and wide for generations to get a peek at the festive, narrative window displays outside the original Marshall Field’s department store on State Street. The store is technically now a Macy’s, but perhaps you’ve noticed that Chicagoans don’t take well to change. (Willis Tower, we’re talking to you!)

Chicago-style deep-dish pizza always hits the spot with its thick, buttery crust and extra-melty mozzarella cheese

This year-round favorite is extra special in the colder months—there’s nothing like a thick, buttery crust and extra-melty mozzarella cheese to keep us warm in subzero temperatures. Our beloved pizzerias also make great gathering spots for friends and family to celebrate the season.

Savor the festive decorations and cocktails at the Palmer House Hotel, a historic building in Chicago

As one of the oldest continually-operating hotels in North America, the Palmer House is one of the most ornate and historic buildings in Chicago. During the holiday season, the Palmer House is dressed to the nines and features a lengthy list of warm seasonal cocktails.

Bobby’s Bike Hike – Holiday Hike

Sample the seasonal and festive local beers of Chicago in decorated local taprooms

With over 200 breweries in the metropolitan area, Chicago has become a craft beer capital of the world. In order to remain competitive in such a robust market, many breweries showcase seasonal drafts between November and January to bring the flavors of the holidays right to your pint glass. Stop by any local taproom for more info, or ask a server at most downtown Chicago restaurants what they have to offer.

Indulge in the original chocolate brownie at Palmer House Hotel for a holiday treat

The holidays are a time to splurge and enjoy the sweetness of the season! No treat is quite as classic to Chicago as the chocolate brownie. The brownie was invented at the Palmer House Hotel in 1893 as a portable dessert for guests visiting the World’s Fair. Today, the original recipe for the chocolate brownie is still served with walnuts and an apricot glaze.

 

There you have it! See if you can tick off all the Chicago holiday attractions on the list. We recommend working up an appetite by ice skating so you can indulge in all the goodies at the Chicago Christmas market, Christkindlmarket!

Let us take care of the planning for you and join us on our Holiday Hike Season Sampling Food and Walking Tour for a full tour and sample of Chicago’s festive attractions!

 

Chicago Holiday Tours with Bobby's Bike Hike