If you’re looking for something festive, the Christkindlmarket is a cozy outdoor holiday market inspired by traditional German Christmas villages. You’ll find warm drinks, handmade ornaments, and seasonal treats in a charming downtown setting. It’s a fun way to soak up some holiday spirit during your weekend in Chicago.
Experience the historic home of the former Marshall Field and Company, one of the world's great department stores! A Chicago exclusive established in 1852, Marshall Field's was a pioneer in the retail business and established many of the standard practices we take for granted such as the bridal registry, personal shoppers, book signings, and in-store dining. With 72 acres of retail space complete and the largest Tiffany glass dome in the world, this building continues to impress despite the Marshall Field's brand being bought out by Macy's in 2006. Sharing a meal under the great tree in the famous Walnut Room is a Chicago tradition going back generations.
Check out Cloud Gate (aka “The Bean”) in Millennium Park—a mirrored sculpture that reflects the skyline and surroundings. It’s just a short ride from the hotel and makes a great spot for a walk, a quick photo, or simply to take in the city.
For a fun winter activity, check out the skating ribbon at Maggie Daley Park. It winds through the park with skyline views and is a great way to enjoy the season. Be sure to reserve tickets in advance—they often sell out and do not accept walk-ins. You can book online through the park's website.
Walk straight north on State St from the hotel to experience the waterfront and skyline!
Pizano’s is our go-to for deep dish when we’re craving something classic and comforting. The crust is perfectly crisp, the sauce has great flavor, and it’s consistently solid. Definitely worth a stop if you’re in the mood for a laid-back Chicago pizza spot.
One of our go-to spots in the city, this restaurant serves dim sum all day and never disappoints. The menu has all the classics—dumplings, buns, and crispy bites—served fresh and made to share. It’s casual, consistently good, and always hits the spot. You HAVE to try the shumai!
The Berghoff is a longtime Chicago favorite with a cozy, old-school feel and solid German-inspired food. The menu has everything from bratwurst to schnitzel, plus their own house-brewed beer. It’s a great spot for a hearty meal in a historic setting without feeling overly touristy.
The Walnut Room is a Chicago holiday classic, especially this time of year. It’s known for its beautiful dining room and the giant Christmas tree at the center of it all. The food is great, but the atmosphere is what makes it special. Be sure to make a reservation well in advance—it can book out months ahead during the season. Totally worth it for the festive experience.