Discover the Magic of the Season: Chicago Holiday Scavenger Hunt
- Wander & Host
- Nov 16, 2024
- 6 min read
Updated: Jan 16
As Chicago lights up for the holiday season, there’s no better way to explore its unique flavors and festive spirit than with a holiday scavenger hunt through the city.
This self-guided culinary scavenger hunt through Chicago is a festive way to experience the city’s holiday magic and savor seasonal flavors along the way. Whether you’re a local or a visitor, this adventure will leave you with warm memories and holiday cheer.
So bundle up, grab your friends, and get ready for a holiday stroll through Chicago’s best sights, bites, and festive lights!
Chicago holiday scavenger hunt
This self-guided scavenger hunt is designed to be a fun, flexible way to explore the city. Each stop features a task, a seasonal treat, or a unique activity to complete. Use the interactive map provided to guide you through each location and capture the magic of Chicago’s holiday season.
Starting Point: The Magnificent Mile Holiday Lights
Task: Begin with a stroll down Michigan Avenue to admire the famous holiday lights. Snap a photo of your favorite decorated window display along the way.
Pro Tip: Many stores have special holiday windows, so be sure to look out for the most creative displays.
The holiday lights began in 1949 when the Greater North Michigan Avenue Association decorated a 50-foot Christmas tree in Water Tower Park with 1,500 lights and a six-foot star. In 1959, Saks Fifth Avenue introduced Italian white lights on elm trees in front of their store, inspiring other retailers to join in, creating a unified display of lights along the avenue.
Stop #1: Christkindlmarket at Daley Plaza
Address: 50 W Washington St, Chicago, IL
Task: Grab a hot, spiced glühwein (German mulled wine) served in a collectible holiday mug, and snap a selfie with your mug against the twinkling lights of the market.
Food Challenge: Try a German bratwurst with sauerkraut or Bavarian pretzel, two of the market’s signature snacks.
Bonus Activity: Find a unique holiday ornament from one of the artisan vendors to take home as a souvenir.
The Chicago Christkindlmarket was founded in 1996 by the German American Chamber of Commerce of the Midwest. It was modeled after the historic Christkindlesmarkt in Nuremberg, Germany, which dates back to the 16th century and is one of the most famous Christmas markets in the world.
Stop #2: The Walnut Room at Macy’s on State Street
Address: 111 N State St, Chicago, IL (located on the seventh floor)
Task: Marvel at the Great Tree in the Walnut Room and, if you can get a table, order their famous chicken pot pie or Mrs. Hering’s original pot pie recipe.
Drink Challenge: Toast the season with a seasonal cocktail, like a peppermint martini or eggnog, from the Walnut Room’s holiday menu.
Photo Challenge: Take a picture with the Great Tree in the background. If there’s a live pianist, capture a video clip of your favorite tune.
In 1907, the tradition of the Great Tree started at the Walnut Room. By 1934, it grew to 25 feet, reaching 45 feet in the mid-century. Decorating it became a major event, needing scaffolding and a team for thousands of ornaments and lights.
Stop #3: Millennium Park and Maggie Daley Park
Address: 201 E Randolph St, Chicago, IL
Task: Visit Millennium Park’s famous ice skating rink, where you can either take a lap or grab a hot chocolate from nearby stands to enjoy while watching the skaters.
Photo Challenge: Take a selfie with “The Bean” (Cloud Gate) covered in snow or surrounded by holiday lights.
Extra Fun: Check out Maggie Daley Park’s skating ribbon for a unique, winding skating experience through the park.
The park spans 24.5 acres and is built over active rail lines and parking garages, showcasing Chicago's history of architectural ingenuity.
Stop #4: Garrett Popcorn Shop
Address: 625 N Michigan Ave, Chicago, IL (Various locations)
Task: Stop by Garrett Popcorn for a taste of their famous Chicago Mix (cheddar and caramel popcorn) or one of their holiday flavors.
Food Challenge: Grab a small bag and share your favorite popcorn flavor with a friend, or buy a seasonal tin as a gift.
Photo Challenge: Take a picture of your popcorn with the city lights in the background.
Founded in 1949 in Chicago, Illinois. The first store opened at 10 West Madison Street, near the bustling State Street corridor. The recipes for several of its popcorn flavors are trade secrets based on family recipes.
Stop #5: Eataly Chicago Holiday Market
Address: 43 E Ohio St, Chicago, IL
Task: Browse Eataly’s seasonal market for Italian holiday treats like panettone, torrone (Italian nougat), or Christmas cookies.
Food Challenge: Sample a festive Italian pastry and pick up a mini panettone to bring home.
Drink Challenge: Warm up with a glass of Italian vin brulé (mulled wine) or a festive Aperol spritz.
Bonus Challenge: Try to find three different Italian holiday ingredients that would be perfect for a Christmas charcuterie board.
Eataly, founded in Turin, Italy, in 2007 by Oscar Farinetti, was conceived as more than just a store. Farinetti envisioned a place where people could eat, shop, and learn about high-quality Italian food and culture. This philosophy was brought to Chicago in 2013, creating a space that celebrates Italian gastronomy and traditions.
Stop #6: The Peninsula Hotel Sky Rink and Chalet
Address: 108 E Superior St, Chicago, IL
Task: Head up to the rooftop Sky Rink, where you can rent skates and enjoy the unique experience of rooftop skating.
Food Challenge: Visit the cozy chalet next to the rink and try their holiday-themed s’mores or a mug of hot chocolate with whipped cream.
Photo Challenge: Take a photo with the Chicago skyline in the background as you sip on your festive treat.
Debuting in November 2012, the 2,100-square-foot Sky Rink is situated on the hotel's fourth-floor terrace, providing guests with a unique skating experience amidst the city's skyline. The rink is surrounded by festive decorations, including twinkling lights and holiday music, creating a winter wonderland atmosphere.
Stop #7: The Drake Hotel’s Holiday Tea Room
Address: 140 E Walton Pl, Chicago, IL
Task: Book a seat for the Drake’s iconic holiday tea experience (reservations are recommended). Indulge in tea sandwiches, holiday pastries, and scones with clotted cream.
Drink Challenge: Enjoy their classic holiday tea service, or request a holiday cocktail like a champagne spritzer.
Photo Challenge: Take a picture in front of the Drake’s festively decorated lobby, especially if the hotel’s large Christmas tree is on display.
Since the hotel's opening on New Year's Eve in 1920, the Palm Court has been a central gathering place for afternoon tea, hosting Chicago's social elite daily—a tradition that continues to this day.
End Point: ZooLights at Lincoln Park Zoo
Address: 2001 N Clark St, Chicago, IL
Task: Cap off your scavenger hunt with a visit to ZooLights, where the Lincoln Park Zoo is transformed into a holiday wonderland with millions of lights.
Food Challenge: Grab a warm churro, a holiday cookie, or a cup of spiked hot chocolate from the stands around the zoo.
Photo Challenge: Take a picture in front of your favorite holiday light display to complete your scavenger hunt.
ZooLights at Lincoln Park Zoo is a cherished Chicago holiday tradition that has illuminated the zoo during the festive season for three decades. Established in 1994, this annual event transforms the zoo into a winter wonderland, attracting visitors of all ages to experience its enchanting displays and activities.
Bonus Challenges Throughout the Hunt
Holiday Selfie Challenge: Take at least five holiday-themed selfies throughout the scavenger hunt and create a collage at the end.
Festive Fact-Finding: Find out one unique historical fact about each location and share it with friends at the end of the hunt.
Seasonal Cheers Challenge: Try at least three different holiday beverages throughout the hunt, from hot chocolate to mulled wine and seasonal cocktails.
Bonus Experiences in Chicago for the Holidays
Discover two hidden holiday gems in Chicago loved by locals.
The Christmas Around the World and Holidays of Light Exhibit at the Museum of Science and Industry
Since 1942, the Museum of Science and Industry has hosted the "Christmas Around the World" exhibit, featuring a grand 45-foot tree surrounded by over 50 smaller trees, each decorated to represent holiday traditions from cultures around the globe. The "Holidays of Light" component highlights celebrations such as Hanukkah, Kwanzaa, Diwali, and Ramadan, offering a rich tapestry of global festivities. This exhibit provides a unique opportunity to explore diverse cultural traditions in a single venue.
The Art Institute of Chicago's Thorne Miniature Rooms Holiday Decorations
The Art Institute's Thorne Miniature Rooms are a collection of 68 intricately crafted miniature interiors representing various time periods and regions. During the holiday season, select rooms are adorned with festive decorations appropriate to their era and locale, such as a Victorian Christmas tree or a Colonial American holiday table setting. This seasonal embellishment offers a charming glimpse into historical holiday celebrations on a miniature scale.
These experiences provide a deeper appreciation of Chicago's rich cultural tapestry and are beloved by those familiar with the city's holiday offerings.
Tips for a Successful Holiday Scavenger Hunt
Plan Your Route: Since Chicago’s holiday events can draw crowds, consider starting in the morning to avoid long lines, especially at iconic spots like the Christkindlmarket and Millennium Park.
Dress Warmly: Chicago winters are chilly, so layer up and bring gloves, hats, and a warm coat to enjoy the outdoor stops.
Bring Friends or Go Solo: This hunt is a fun way to spend time with friends, but it’s also perfect for a solo adventure or a holiday date.
Capture the Moments: Make sure to document your journey through photos and share your favorite spots on social media to spread the holiday cheer.
For more information on Chicago’s holiday events, including operating hours and ticket reservations for specific venues, check out the official Choose Chicago Holiday Events Guide.