Christmas in ChicagoCouples/Groups

Day 1

Arrive in Chicago

Holiday brunch can be found all over the city. Atwood Café is decorated with classy wreaths and trees. Dinkel’s Bakery & Cafe displays a Christmas village complete with candy cane houses and a trolley track.

Enjoy a walk through Millennium Park, where you can ice skate in the shadow of Cloud Gate (known as “The Bean”) or along the ice skating ribbon at Maggie Daley Park. Make sure you join in with the Caroling at Cloud Gate.

Nearby Macy’s on State Street will awe you with its famous holiday window displays. Then head inside to The Walnut Room for a holiday pot pie or sparkling poinsettia cocktail. You’ll also see the enormous Great Tree, a 111-year tradition.

The ‘Holiday Lights, City Lights’ tour, put on by the Chicago Architecture Center and Big Bus Tours, will give you a glimpse of Chicago’s architectural highlights all lit up for the holidays.

360 CHICAGO offers stunning views over the city from their 94th floor observation deck. Have a swanky cocktail one floor down at the Signature Room. For a classic Chicago meal, Pizzeria Uno or Gino’s East will give you a taste of deep-dish pizza.

Theaters throughout the city stage a variety of holiday shows, including the Joffrey Ballet’s ‘Swan Lake’ and ‘Nutcracker,’ and the Goodman Theatre’s ‘Christmas Carol.’ Broadway In Chicago also runs 2-4 different shows at any given time.

If you’re into sports, head to a Chicago Bulls basketball game or Chicago Blackhawks hockey match for an action-packed evening at the United Center.

Day 2

Beatrix serves a healthy, all-American breakfast. The LB Bistro & Patisserie bakes up French sweets & savory breakfast options.

For family fun, visit the enchanting Navy Pier Winter Wonder Fest featuring a carousel, ice-skating rink, giant Christmas tree, and more at this indoor wonderland. Then enjoy a ride in one the Centennial Wheel’s heated cabins. Grab lunch at one of Navy Pier’s many Chicago favorite restaurants, including DMK Burger Bar, Riva Crab House, Billy Goat Tavern, or Giordano’s.

Take a quick ride on the CTA Holiday Train, a decked out ‘L’ train complete with Santa’s elves and take a picture with Santa Claus.

Afterwards visit Christkindl market in Daley Plaza, Chicago’s very own authentic German Christmas market. Here you can enjoy hot spiced-wine or cocoa, delicious bratwurst, and potato pancakes while shopping for everything from handmade Christmas ornaments to artesian cheeses.

Once the sun is down, go to Lincoln Park Zoo, one of the oldest free zoos in the country. During ZooLights, the grounds are covered in millions of twinkling lights for a truly magical holiday display

If you’d like to end with a festive nightcap go to Butch McGuire’s in Gold Coast, a bar that goes all out decorating for the holidays. For an authentic Chicago blues experience go to Kingston Mines in Lincoln Park, open 365 days a year until 4 a.m!

Day 3

Start your third day with a bite at French-inspired Cochon Volant Brasserie in the Loop PRIOR TO CHECK OUT.

Get a multi-cultural Christmas experience at the annual ‘Christmas Around the World’ exhibition at the Museum of Science and Industry, where you’ll find trees decorated to represent 50 countries.

After your museum adventure, head to the Palmer House Hotel in the Loop for a hot cocoa in their breathtaking lobby. This legendary social hub was visited by Charles Dickens, Frank Sinatra, and more. Did you know the chocolate brownie was invented here, and you can still try the original recipe there today?

The Drake Hotel’s beautiful Palm Court is worth a visit for a high tea that’s steeped in Chicago tradition. Christmas carolers make their rounds to the guests who can request the classics. Be sure to book ahead to reserve your spot.

If you’re lucky enough to be in town the weekend before Thanksgiving, make your way up to Michigan Avenue for the nationally televised Magnificent Mile Lights Festival. The festival features a parade led by Mickey Mouse and a fireworks show. The Magnificent Mile is home to over 460 retail stores including two shopping malls, The Shops at Northbridge and Water Tower Place.

For a classy dinner experience and a tour of the skyline via the Chicago River, book the Odyssey Chicago River Cruise. A heated or glass enclosed boat that runs year-round.

The Godfrey Hotel features a heated outdoor rooftop with igloos, firepits and s’mores kits. Cindy’s Rooftop at the Chicago Athletic Association hotel offers hot cocktails and fire pits for the winter months and overlooks Millennium Park. It’s a wonderful place to end your holiday trip to Chicago.

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