Top Illinois Christmas Tours

Stroll through Chicago's winter streets, lit up for the holidays, without the hassle of navigating the city yourself on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk.

We invite you to join us on a holiday themed, festive and fun foodie adventure! This tour is just like our normal food tour, but with a holiday twist! Dig out those ugly Christmas sweaters and get ready to see the Hallmark of the Midwest in a new and foodie way. PLUS, rock out that ugly sweater and you will be in our contest to win a free tour! You will join your festive foodie guide down the famous Main Street of Galena enjoying some of the best food and drinks the town has to offer. Definitely bring an empty stomach and your holiday cheer!

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks, DJ entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the Potomac River with your friends and family. Happy Holidays Includes Three-hour Christmas Eve dinner cruise on the Potomac River Chef-prepared, three-course, plated holiday menu The most breathtaking views of the nation's greatest landmarks including the Washington Monument and Lincoln Memorial DJ entertainment Complimentary coffee, hot tea, and iced tea

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Come bundled and join your guide and small group to explore the famous Christkindlmarket. Then continue to discover Millennium Park’s ice rink and Christmas tree, stroll the Magnificent Mile’s glowing lights, and more while you hear fun facts and cultural insights from your guide.

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do European holiday customs shape winter traditions in American cities? Along State Street, seasonal décor reflects a long-standing retail heritage. The Christkindlmarket introduces a cultural tradition rooted in German history and craftsmanship. Wooden stalls and artisan goods echo centuries-old holiday markets of Europe. This experience blends festive atmosphere with cultural continuity in a refined city setting. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!