The Best Ways to Celebrate the Holidays in Chicago Like a Local Image

The Best Ways to Celebrate the Holidays in Chicago Like a Local

Chicago, one of the most iconic cities in the world, is high on the holiday wish list and locals know best when it comes to where to go, what to do and how to add that dazzle to the season. From holiday-themed pop-ups and festive performances, to an inside scoop on the best centrally-located places to stay, travelers can make their season bright with tips and tricks on how to do Chicago like a local this year.


A Second City Christmas

A local favorite, catch a show full of holiday cheer at the Second City comedy club –Chicago’s legendary performance theater with notable alumni include Steve Carell and Tina Fey. They’re celebrating the season with several holiday-filled shows including ‘A Snow Globe Kissmas’, ‘The Holiday Batch’, ‘An Upper Middle-Class Christmas’ and ‘A Christmas Carol: Remembered’.


The Curling Cabin at the Gwen

A city favorite, the Gwen’s Curling Cabin pop-up is open again for the season, adjacent to the Magnificent Mile. Visitors can dash over to their terrace space decked in winter gear to keep visitors warm with an outdoor fireplace, heated lamps, and hot cocktails. Twinkling lights and flannel décor are the perfect backdrop to try a hand at curling for $25 per person for 30 minutes of playing time. The space is open through the holiday season.


Holiday Windows at Macy’s State Street

Join generations of Chicagoans to shop through this historic holiday shopping destination. Recognized as a National Historic Landmark, Macy's State Street is a true holiday must-do and see. While there, visitors can sit down for a holiday meal at The Walnut Room –one of Chicago's most beloved restaurants, especially during the winter season. Enjoy a traditional pot pie made from Mrs. Hering's and dine alongside a lighted 45-foot Great Tree that graces the restaurant each November through early January.


Caroling at Cloud Gate

Tourists and locals can head to Millennium Park this season to sing-along holiday classics around the city’s famous “Bean.” Free to attend and a short walk to the McCormick Tribune Ice Rink, it’s easy to get in the holiday spirit through music and cheer.


To make the most of the holidays, travelers can enjoy easy access to Chicago’s best activities and celebrate the season like a local by staying at the newly-renovated The St. Clair Hotel™ – Magnificent Mile. With rates starting at $79, Red Roof’s first Red Collection property, puts visitors in a prime location at the intersection of St. Clair and Ontario in Streeterville to experience all that the holidays have to offer in Chicago.

Red Roof Logo
Or call 1-800-733-7663

RediCard Members

Close
Forgot your password?
Join Redicard

Start Earning Rewards with Your First Stay

The fastest way to free nights and other rewards!

View all program details

NOT A REDICARD MEMBER?

JOIN REDICARD

Sign In Help

Forgot your username or password? No problem. We can email you information for updating this.

If you need further assistance, please call us at 1-800-733-7663

Contact Information (Optional)


Enter your other contact info now and save time when you book reservations.