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.
Lace up your skates at 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.
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.