Working with our clients in Chicago for the past 10 years has given us expert knowledge about happenings around the city.

We’re often asked about the best events and activities to do in Chicago in the winter. Christmas shows are a can’t-miss during the holiday season.

With a wide assortment of shows ranging from Dickens to modern parodies, these holiday shows are guaranteed to keep you entertained and excited during the winter season.

The Nutcracker at the Auditorium Theatre

Watch the Joffrey Ballet perform the Christmas classic The Nutcracker this holiday season at the Auditorium Theatre. This version of the Nutcracker has been reimagined around iconic Chicago history with the ballet now taking place at the 1893 Chicago World’s Fair.

The Auditorium Theatre sits across the street from Millennium Park. For upscale tapas before the show, stop by Mercat a la Planxa. To keep the Christmas spirit before the ballet, grab a warm cup of tea at Russian Tea Time in the Loop.

‘Twas the Night Before Christmas

‘Twas the Night Before Christmas is presented by the Emerald City Theatre at the Broadway Playhouse in Water Tower Place. This short, but exciting family-focused show follows elves, mice, and other Christmas characters through the North Pole on an adventure to find Santa’s missing list. Don’t forget to grab a post-show beverage at the after party and meet the cast over hot chocolate and pastries. This is great for those living in Gold Coast or Streeterville because residents can walk and enjoy the holiday lights along the way!

Water Tower Place is already the perfect spot to bring your family since it’s filled with wonderful dining and shopping options. Highlights include a full-service Harry Caray’s and quicker options such as M Burger, Da Lobsta, and Wow Bao.

A Christmas Carol

Watch the classic Dickens story of Christmas spirit with A Christmas Carol at the Goodman Theatre. Playing every holiday season since 1978, the Goodman Theater’s production of a Christmas Carol has become a Chicago tradition passed through many generations.

The Goodman Theatre is located in the Loop, just south of the river. Before the show, drop by Christkindlmarket to stay in the holiday spirit and then grab dinner at one of the many upscale dining options in the area such as Atwood or Catch 35.

White Christmas

It’s not Christmas without the Bing Crosby classic White Christmas. Watch timeless holiday song and dance and have your spirits lifted for over two hours with this fun show. This Broadway in Chicago play is being performed at the Cadillac Palace Theatre in the Loop.

The Loop is filled with great pre-show and post-show dining options. Pierogi Heaven is a cozy and casual polish restaurant with pierogies or try chic American fare at The Dearborn.

Potter Potter

Calling all Harry Potter fans! This hilarious Harry Potter parody captures all seven novels in a mere 70 minutes. Only running in Chicago during the holiday season, don’t miss your chance to reconnect with Harry, Ron, and Hermione.

Potted Potter is running at the Broadway Playhouse in Water Tower Place. If you want a change of pace, consider grabbing your pre-show dinner outside of the mall. Francesca’s on Chestnut is a classic Italian restaurant in Gold Coast guaranteed to fuel you for a night of laughter.

If you’re in the market for a new Chicago apartment or condo and want to experience our city’s best winter events, click the link below!