A Day in Chicago - Holiday Itineraries

Posted on December 04, 2015

Chicago is a beautiful city to experience the magic of the holiday season. Make special memories with families, friends or that special someone with our custom holiday itineraries.

Family Itinerary #1 

Start your morning with Breakfast with Santa and Sue at the Field Museum (Dec 19, 8:30am). Enjoy a buffet breakfast in the historic Stanley Field Hall and have fun creating holiday crafts. After breakfast you'll get to share all of your holiday wishes with Santa when you take your picture with Santa and SUE. Continue your historic morning exploring the Field Museum's exhibits

Head to the Loop for German eats and shopping at the downtown Christkindlmarket in Daley Plaza. The unique shopping experience, typical German food and drinks, as well as diverse holiday entertainment make the Christkindlmarket Chicago a preferred and popular destination every holiday season. 

Hop aboard the CTA Holiday Train (redline) for a magical transport to your next destination! The special six-car train is decked out day and night with holiday seasonal images, twinkling lights inside and out, bows, garland and Santa on his sleigh aboard an open-air flatcar. Definitely a site to see! Disembark in Lincoln Park and head over to Lincoln Park Zoo's ZooLights, a fun, free, family-oriented holiday celebration, featuring luminous displays and holiday-season activities throughout the zoo grounds. Grab dinner before or after at a local neighborhood restaurant like Mon Ami Gabi or a quick bite at the zoo.

Family Itinerary #2 

Start your morning with the Holiday Kids Kart Brunch at Allium in the Four Seasons Hotel Chicago. Kids get to enjoy their own meal without splitting with siblings or parents. The interactive brunch includes special kids' libations, cinnamon rolls with paint-your-own-icing, fruit salad in a jar, delicious entrees, dessert buffet and more. Parents, of course, will have equally delicious Allium menu items to enjoy from Executive Chef Stephen Wambach.

Experience the magic of Chicago Children’s Theatre at A Snowy Day with Beatrix Potter & Friends at the Newberry Library. The stories of Helen Beatrix Potter are brought to life through a 65-minute interactive, four-dimensional winter fairy tale that is perfect for kids ages 2 and up.

After the show, visit the popular, naturally bearded Santa at the 900 North Michigan Shops. Each child that visits Santa will receive a special gift. Parents will enjoy the 70 luxury lifestyle shops for their holiday shopping and other holiday happenings and amenities

Your Chicago holiday memories are not complete without taking a stroll along the bustling Magnificent Mile and seeing the festive holiday window displays and the entire Avenue aglow with a million twinkling lights on 200 trees. Enjoy a casual, mid-level or fancy dinner at any of the many restaurants on and around The Magnificent Mile.


Delicious brunch options abound in Chicago - the problem isn't finding a good place, it is narrowing down which to go to! Consider Beatrix, a popular LEYE restaurant with two locations in the Streeterville and River North neighborhoods.

Get your shop on with holiday shopping along State Street in the Loop, another popular Chicago shopping destination. Enjoy a coffee as you stroll the Avenue and be sure to visit Macy's famous holiday windows. See Choose Chicago's 2015 Guide to Holiday Shopping in Chicago.

Choose from numerous holiday theatre performances - from classics like It's a Wonderful Life and A Christmas Carol, to light-hearted options like A Charlie Brown Christmas and Holiday Bingo. Choose your holiday show and then pick a nearby restaurant for pre-show or post-show eats and holiday drinks to top off your festive day.


Enjoy a leisurely late-morning brunch at Pierrot Gourmet in The Peninsula Chicago, a European-style café and bistro with a cozy farmhouse-inspired ambience. Menu items include Popover With Chicken & Sweet Potato Hash and the Brioche French Toast, just to name a few mouth-watering dishes.

Plan a couples massage at The Peninsula Spa or a channel your inner child with a skate around The Peninsula Sky Rink. Surrounded by Chicago’s skyscrapers and twinkling lights, the rink is tucked into a pine tree winter wonderland and bathed in festive music and snowflake lighting. Choose from a selection of hot beverages and snacks to sip amid the heated lounge area in between skates on the rink.

See one of the best ballet companys in the world perform Robert Joffrey's version of The Nutcracker for the last time. Don't miss this lavish, beloved holiday tradition, with Tchaikovsky's score performed live by The Chicago Philharmonic. Before or after the show, grab dinner and drinks at nearby favorites like Petterino's, Park Grill, The Gage, Trattoria No. 10, Harry Caray's Restaurant, and more.

More ideas to enjoy the holidays in Chicago:

Christmas Around the World at The Museum of Science and Industry

Holiday Lights, City Lights with the Chicago Architecture Foundation

Holiday Tea at The Drake Hotel

Snow Much Fun at the Chicago Children's Museum

5 Places to Ice Skate in Chicago

Chicago Trolley Holiday Lights Tours

400 Tubas Christmas Concert