The Essential Itinerary: Chicago for the holidays

Chicago goes BIG for the holidays. Here are our picks for the best ways to celebrate the season on a weekend getaway to the Windy City.

  • Nov 30, 2021
  • 856 words
  • 4 minutes
The holiday season in Chicago starts with the lighting of the Christmas tree in Millennium Park on the third weekend in November. (Photo: Choose Chicago)
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Chicago — famous for baseball, architecture, deep-dish pizza, and culturally diverse neighbourhoods — offers plenty of festive attractions for tourists and locals alike during the holidays. All you need is a few hours in Chicago to understand why it consistently tops lists of the best cities in the United States. Here’s your essential itinerary for a weekend trip to Chi-town this holiday season. 

Day 1

12 p.m.: Check off your shopping list
Inspired by a German tradition dating back to the 16th century, Chicago’s Christkindlmarket features handmade goods, German food and drink and live performances in a festive setting. (Photo: Choose Chicago)
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Get your holiday shopping done at the Christkindlmarket, where you’ll find unique hand-crafted gifts by different exhibitors. Inspired by the 16th century Christkindlmarkt in Germany, Chicago’s own Christkindlmarket has been an annual tradition since 1996, and this outdoor market combines local Chicago flavour with European holiday traditions in an open air space with dozens of Christmas shopping booths, German food and drinks, festive musical performances, and more. 

4 p.m.: Light up your night

A Chicago tradition, the annual ZooLights at Lincoln Park Zoo is a popular outdoor attraction. The entire zoo grounds are illuminated with dazzling Christmas lights and dynamic light displays. This twinkling winter wonderland is complete with a holiday pop-up bar, an Enchanted Forest, a light maze, and sweet treats — a must-see when you’re in Chicago for the holidays. ZooLights runs until January 2, 2022.

ZooLights transforms the Lincoln Park Zoo into a twinkling winter wonderland the entire family will love exploring. (Photo: Choose Chicago)
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6 p.m.: Sing in the season

Before heading out to dinner (Gibson’s Steakhouse is a great idea), head over to the famous Cloud Gate, also known as “The Bean.” The Bean is located in Millennium Park, where you’ll also find the stunning illuminated Chicago Christmas tree. The Christmas tree is donated by a local family every year. The lighting of the tree takes place on the third weekend in November and officially kicks off the holiday season in the city. While taking in the lights, stay for the Holiday Sing-Along, held every Friday until December 17 starting at 6 p.m.

Day 2

9 a.m.: Eye in the sky

Beat the crowds and head to the Skydeck at the 442-metre-high Willis Tower early in the morning. Your visit begins with a walk through the brand new Chicago-themed museum, an immersive experience showcasing things the Windy City is famous for. Next, take the elevator up to the 103rd floor to take in the spectacular views from the observation deck. On a clear day, you can see as many as four different states! If you don’t have a fear of heights, step out onto The Ledge (there are four glass viewing boxes for you to choose from) to see even more incredible views through the glass floor. 

12 p.m.: Savour authentic flavours
Tzuco features authentic Mexican cuisine as imagined by Michelin-starred chef Carlos Gaytán. (Photo: Loukia Zigoumis)
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If your taste buds need a break from hot chocolate and candy canes, a visit to Tzuco will do just the trick. This authentic Mexican restaurant features a distinct yet accessible menu created by Michelin-starred chef Carlos Gaytán. Try the homemade guacamole, fish tacos, and avocado flatbread paired with traditional margaritas. The ambiance is also top-notch, with floor-to-ceiling windows and clear glass boxes framed with indigenous wood containing preserved artifacts from Gaytán’s homeland. 

2 p.m.: Explore the Magnificent Mile

Starting in November, the Magnificent Mile is lit up for the holidays, and it’s a sight to behold. In addition to high-end boutiques, award-winning restaurants, and five-star hotels, this iconic neighbourhood is worth exploring for its landmark architecture. If the wind picks up off Lake Michigan and the temperature drops, pop into Water Tower Place, an enormous eight-level shopping centre. 

5 p.m.: Dinner and a show

After you’ve shopped ‘till you dropped, it’s time to get ready for dinner — check out Athena Restaurant in Greektown for some traditional Greek food — and a show. A new musical has arrived in Chicago called Paradise Square, following the lives of Irish and Black immigrants in New York City’s once-infamous Five Points neighbourhood living together through the violent Civil War Draft Riots of 1863. The musical is a celebration of community coming together through tears, laughter, and of course, music. After its run at Chicago’s James M. Nederlander Theatre (until Dec. 5), Paradise Square hits Broadway in NYC.

Where to stay
The Langham Chicago is a sleek, chic hotel in the heart of the action. (Photo: Langham Chicago)
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The Langham Chicago is a stunning property to call home during your stay, located in the heart of the city’s downtown core, with incredible views of the Chicago River and Lake Michigan. Minutes away from the famous Chicago sign, Magnificent Mile, and Millennium Park, the hotel was designed by renowned architect Mies van der Rohe, and features 316 luxurious rooms and suites, all with floor-to-ceiling windows. The Langham Club Lounge, located on the 12th floor, offers a complimentary breakfast buffet, all-day refreshments, evening cocktails and appetizers, a writer’s corner, library, and two computer workstations. The hotel’s restaurant, Travelle, is a great spot for dinner or late night drinks, and you can also enjoy a classic Langham afternoon tea at the Pavillion. In your downtime, make sure to visit the Chaun Spa, swimming pool, and fitness centre. 


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