BEST Festive Things to do in Chicago at Christmas 2023 (From a Local!)

Dine at the Walnut Room

Dining at the Walnut Room is a legendary Chicago holiday tradition. Located on the 7th floor of Macy’s State Street (formerly Marshall Fields), the Walnut Room was the first restaurant ever opened in a department store. During the holiday season diners can enjoy the view of the Macy’s “Great Tree” in the middle of the restaurant while feasting on holiday classic dishes such as Mrs. Hering’s 1890 Original Chicken Pot Pie.

Where: 7th floor at Macy’s State Street at 111 N. State Street, Chicago, IL

When: The Great Tree will be lit through Sunday, January 7, 2024.

Go Outdoor Ice Skating

One of the best and picture perfect spots to go ice skating in Chicago is the McCormick Tribune Ice Rink right in front of The Bean. Admission is free, but online reservations are required.

Another popular option is the skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink. Tickets will be released on a rolling basis at (noon) every 2 weeks.

Here is a list of the best outdoor ice skating rinks in Chicago with hours, prices and other information.

Ride the CTA Holiday Train and Bus

 

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The CTA Holiday Train is a holiday tradition unique to Chicago. As the train pulls into each station, Santa waves to riders from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees. Each car of the train is wrapped with holiday and seasonal images. Thousands of twinkling lights outline the shape of the train and windows, with even more lights running across the tops of the cars. (The video above is from one of my favorite Chicago photo spots.)

The CTA Holiday Bus is 60-foot bus turned into a winter wonderland with holiday music playing and Santa waving and from the roof-hatch of the bus. The exterior of the bus features Chicago’s skyline one snowy evening with “Ralphie the Reindeer” leading the way, his nose aglow and Santa’s sleigh in tow. Festive strings of lights outline the bus and its windows, along with sparkling snowflakes that light-up at night.

When: See transitchicago.com/holidayfleet for full details on dates, times and routes.

Cost: Regular CTA fare. See transitchicago.com for prices. You can see the bus pass by for free from the street.

THE POLAR EXPRESS Train Ride

THE POLAR EXPRESS™ Train Ride is a re-creation of the classic children’s story on board a real train. Passengers are served hot chocolate and a treat by dancing chefs, enjoy a reading of the book by Chris Van Allsburg, and receive the first gift of Christmas after Santa boards the train to greet families. Performers engage passengers in caroling and fun holiday activities on the return trip to Union Station. The train ride lasts an hour and passengers are encouraged to wear pajamas. 

Where: Train leaves and returns from Chicago Union Station at 500 W Jackson Blvd., Chicago, IL 60606.

When: Select dates and times from December 3, 2023 to January 1, 2024. Tickets are on sale now and sell out quickly.

Cost: Pricing varies by date. Visit their website for pricing and to buy tickets.

Winterland at Gallagher Way

Winterland at Gallagher Way is back with family-friendly festivities both at Gallagher Way and inside historic Wrigley Field, including new experiences and returning favorites like the Christkindlmarket Wrigleyville and the Gallagher Ice Rink.

When: Open through January 7, 2024.

Where: Gallagher Way, 3635 N Clark St, Chicago, IL 60613

Cost: See prices and purchase tickets in advance here.

Go Holiday Shopping (or Window Shopping)

Chicago is a great city for shopping with every type of store you can imagine.  Many shopping centers and departments stores have holiday decorations and attractions to put you in a festive mood.  Make sure not to miss Macy’s State Street (formerly Marshall Fields) – the building is a National Historic Landmark and it is known for its holiday window displays.

The major shopping areas in downtown Chicago include State Street (where you can find Macy’s, Target and many smaller stores) and The Magnificent Mile (where you can find three shopping centers, luxury designers and labels, several departments stores and popular brands).

If you are looking for unique and/or handmade items, check out these holiday markets: Chicago Artisan Market (December 3 & 16-17, 2023), One of a Kind Show (December 7-10, 2023), Sauced The Night Market Before Xmas (December 8-9, 2023) and Renegade Craft Fair (December 16-17, 2023).

Watch Classic Holiday Movies at Gallagher Way

Watch classic holiday movies outside at Gallagher Way. While you are Gallagher Way, you can also visit Winterland as well as the Wrigleyville location of Christkindlmarket. The movie schedule is as follows:

• December 7: The Grinch
• December 14: National Lampoon’s Christmas Vacation
• December 21: The Muppet Christmas Carol

Where: Gallagher Way, 3635 N Clark St, Chicago, IL 60613

When: Thursdays from December 2-23 starting at 6 p.m.

Cost:  Free.

See a Christmas Show

Get in the holiday spirit with a Christmas show. There are many holiday shows you can see in Chicago this year, including:

• Joffrey Ballet -The Nutcracker
• Charles Dickens’ A Christmas Carol
• Mannheim Steamroller Christmas

This is a great list of all the holiday shows in Chicago.

Drink Glogg at Simon’s Tavern

Drinking the signature glögg (mulled wine) at Simon’s Tavern is a holiday tradition for Chicagoans.

The long standing neighborhood dive bar in Andersonville is packed every year during the holiday season.

Where: Simon’s Tavern, 5210 N Clark St, Chicago, IL

Drink at a Christmas Themed Pop-Up Bar

Chicago has several holiday pop-up bars that open just for the holiday season. These bars offer holiday decorations, themed cocktails and snacks and more festive touches. Advance reservations are recommended as they tend to be very popular. Some of the best holiday themed bars include:

Nutcracker Bar & Hotel (100 E Chestnut St)
Frosty’s Bar (809 W Evergreen Ave)
Santa Baby Bar (3505 N Clark Street)
Elfd’d Up (Stretch Bar & Grill, 3485 N. Clark Street)
Reindeer Room (1807 S Allport St)
8 Crazy Nights Chicago (3441 N Sheffield Ave)- Chicago’s first Hanukkah pop-up

Walk the Illuminated Light Trail at Lightscape

Lightscape is an after-dark, illuminated trail with thousands of twinkling lights at the Chicago Botanic Garden. Ok so this is technically not in Chicago but it is in the suburbs only a 30 minute drive from downtown. Book early – tickets have sold out the last few years.

When:  Through January 7, 2024.

Where: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022 (24 miles north of downtown Chicago)

Cost: Tickets for adults start at $30 and tickets for kids 3-12 start at $17. Children 2 and under are free. See https://www.chicagobotanic.org/lightscape for prices and to purchase tickets in advance.

Illumination: Tree Lights at The Morton Arboretum

Illumination: Tree Lights at The Morton Arboretum is a one-of-a-kind, interactive spectacle of color, light, and sound that has been delighting audiences since 2013. Be surrounded by color as you walk a one-mile paved path amid interactive lighting effects that highlight the beauty of trees in winter.

When: Through January 6, 2024.

Where: Morton Arboretum, 4100 Illinois Route 53, Lisle, IL 60532 (28 miles west of downtown Chicago)