season's greetings from the second city

There's a storybook magic to Chicago during the holidays. The city transforms into a winter wonderland where you can experience holiday traditions from around the world, ice skate with the iconic skyline in the background and shop along the famed Mag Mile surrounded by festive window displays.

Many attractions have reopened with limited capacity or different operating hours. Inquire with attractions ahead of time for up-to-date travel policies and health and safety information.

  • Day 1: Chicago

Begin your visit to the Windy City by heading to the Museum of Science and Industry for Christmas Around the World and Holidays of Light, the museum’s beloved annual celebration. In the midst of a miniature forest, you’ll find a grand, four-story tree, decorated to represent holiday traditions from around the globe. Make sure to grab tickets ahead of time.

You’ll find holiday cheer galore once you return to the heart of the city, especially when perusing the holiday windows at Macy’s on State Street. Be sure to head to the seventh floor to get a glimpse of the famous Great Tree at the Walnut Room, and if you’re hungry, stay for lunch. A Chicago landmark since 1907, the classic restaurant is a holiday tradition for many in its own right — you can still order Mrs. Hering’s famous chicken pot pie, which dates all the way back to 1890. Make sure to make a reservation ahead in advance.

You could always opt for a different iconic food. If you’re in the mood for pizza, stop for some deep dish at Lou Malnati’s or Giordano’s, two of the city’s most legendary pizza joints.

Following your indoor warm-up, venture over to The Art Institute of Chicago for a photo op with the famous lions decked out in their holiday wreaths, before walking to Millennium Park to see the City of Chicago Christmas Tree. 

Secure a selfie at The Bean, then lace up your skates at the Maggie Daley Park for a unique winter experience. Skating with family and friends across this winding, ice-covered path with the city skyline as a backdrop is sure to result in cherished memories. Just remember to make reservations beforehand. 

When it gets dark, head down the Chicago Riverwalk to catch Art on the MART, a 25-story video installation that takes over the side of the Merchandise Mart. During the holiday season, you can expect Nutcracker-inspired projections by Joffrey Ballet and an inspirational tribute to Chicago’s jazz legacy. 

The nights are getting longer, but that just gives you more reason to embrace holiday light shows! Navy Pier is brightening the winter season with Light Up The Lake, a holiday festival that boasts kiddie train rides, Santa’s Merry Main Street, and Chicagoland’s biggest indoor light garden. Get your tickets in advance — they include a ride on the heated Centennial Wheel, giving you a stunning view of the lights across the city.

For dinner, cozy up in the Fulton Market area, where you’ll have trouble choosing between the throng of amazing restaurants within striking distance. Local favorites like the Publican and Duck Duck Goat are always a great choice, and Au Cheval’s burgers routinely win national awards.

For a relaxing, overnight stay, check into one of several celebrated hotels on Michigan Avenue. Having hosted numerous presidents, celebrities and other notorious characters over the years, The Drake is one of the city’s most historic destinations. Or book a room at the InterContinental Chicago, an architectural gem with a rich history of its own.

  • Day 2: Chicago

Start today with more holiday shopping on The Magnificent Mile, home to a few of Chicago’s most famous retail destinations, such as the Shops at North Bridge, the American Girl Placeand Burberry. While you shop, enjoy the illuminated tree lights decorating the length of Michigan Avenue, as well as the brilliant displays in many of the hotel lobbies. 

For an afternoon treat, stop into the five-story Starbucks Reserve Chicago Roastery — the world’s largest Starbucks — and warm up with a hot beverage before heading over to Garrett Popcorn Shops for more holiday treats.

Craving something sweet? On the ground floor of the historic Wrigley Building, you’ll come across Ghirardelli, the perfect place to grab a hot chocolate to go. If you’re itching to escape the cold, the American Writers Museum is a short walk away. Here, you can engage in a cultural exploration of America’s most impactful writers, browsing dynamic exhibitions and thought-provoking installations. 

Alternatively, the kids will love popping into The Dr. Seuss Experience at Water Tower Place. This immersive experience will spark creativity in their young minds, allowing them to step through the imaginative worlds created in nine different Dr. Seuss books.

If you haven’t filled up on holiday treats, make your way to the Loop for a sweet and savory dish at Nutella Cafe Chicago. Or, be spoiled for choice at the expansive Aster Hall food court, where you can select from a range of the city’s most popular restaurants. 

For a true Chicago holiday tradition, catch a matinee performance of The Nutcracker by Joffrey Ballet. Children and adults alike will be enchanted by the sights and songs of this acclaimed Christmas Eve story. Youngsters in the group might instead prefer to see their favorite movie come to life on stage — in which case, you can’t go wrong with Disney’s Frozen the Musical. 

Once darkness falls, gravitate toward the light. Grab tickets to ZooLights, a popular annual tradition at Lincoln Park Zoo. Every year, the animals stay up late as the zoo gets decked out with dozens of festive displays and millions of holiday lights. 

So many lights, so little time! If you’d rather see multiple attractions, the Chicago Holiday Lights Segway Tour is sure to keep the holiday spirit flowing. Every Wednesday through Sunday during the holiday season, you’ll have the opportunity to reserve a gliding, guided tour of the best light displays in the city.

It’s time to sit back, relax, and refuel. Chances are, frequent Chicago visitors are familiar with The Cheesecake Factory and Grand Lux Cafe. If you’re a newbie, though, you’re in for a treat no matter which you choose. 

If you’re not quite ready to retire for the evening, head up to Butch McGuire’s. One of Chicago’s most illustrious pubs any time of year, this place is arguably unmatched in holiday spirit and jovial decor once winter rolls around. Mingle with fellow revelers, crank festive tunes in the jukebox, and dance off all the sweet treats you nibbled earlier in the day.

  • Day 3: Chicago

Begin getaway day at Lou Mitchell’s, the epitome of a nostalgic city diner. Situated at the start of Route 66, it’s known for its award-winning breakfast dishes and the tasty diner donut holes that customers keep coming back for. 

Roasted nuts, fresh pretzels, sausages and hot spiced wine awaits you at the traditional German Christkindlmarket. This unique outdoor market is a well-known destination for festive gifts and holiday cheer, so soak in the family-friendly atmosphere and see what charming ornaments and treasures you can discover. If you get hungry as you stroll the market, grab lunch from one of the food vendors before you depart.