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 ten 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!

1. The municipal 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.

2, 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!

3. The Maggie Daley Park Ice Skating Ribbon

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

4. Christkindlmarket

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!

5. Traditional German bratwurst

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.

6. The 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!)

7. Chicago-style deep dish pizza

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.

8. Festive decorations and cocktails at the Palmer House Hotel

As one of the oldest continually-operating hotels in North America, the Palmer House is one of the most ornate and historic buildings in the city. 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

9. Seasonal local beer samples

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 restaurants what they have to offer.

10. The original chocolate brownie

The holidays are a time to splurge and enjoy the sweetness of the season! No treat is quite as classically 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 brownie is still served, with walnuts and an apricot glaze.

There you have it! See if you can tick off all the 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!

Book now!