Discover Chicago’s festive magic on a charming holiday walking tour. Explore sparkling decorations, cozy stops, and traditions that make the city shine at Christmas.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; requires comfortable walking ability over city sidewalks.
Wildlife
History
Chicago has a longstanding tradition of lavish holiday celebrations, with downtown decorations dating back over a century.
Conservation
Local walking tours encourage sustainable tourism by promoting pedestrian exploration, reducing reliance on motorized transportation.
Inside Chicago Walking Tours
Discover Chicago’s festive magic on a charming holiday walking tour. Explore sparkling decorations, cozy stops, and traditions that make the city shine at Christmas.
Inside Chicago Walking Tours offers immersive, expert-led walking tours across Chicago, Illinois, showcasing the city's film locations, architecture, history, neighborhoods, and seasonal celebrations. Tours include 2-hour experiences such as Lights, Camera, Alleys: Chicago in the Movies, a movie-focused walk through iconic filming locations led by a passionate movie expert; Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour, a spine-chilling exploration of haunted history and notorious events; Chicago in the Roaring '20s: Art Deco, Flappers, Gangsters, & Prohibition, which highlights Art Deco architecture and Prohibition-era stories; and The World Within (Part Two): Secret Interiors of the Riverfront, revealing glamorous Art Deco details and vaulted lobbies along the Chicago River.
Other offerings include From Great to Grave: Architectural Masters in Life & Death (Graceland Cemetery Tour), which combines architectural history with visits to Graceland Cemetery gravesites; Two Truths & a Lie: Debunking Architecture Tour Myths & Urban Legends, an interactive myth-busting format supported by architect insights; The Christmas Tree Crawl: The Magic of Chicago at the Holidays, a seasonal pop-up tour that uncovers decorations, traditions, and warm indoor stops; and Chicago by Red Line: Chinatown, a neighborhood-focused trip ending in Chinatown’s culinary area. Tours emphasize close-up views, secret interiors, nostalgic film trivia, and historical storytelling.
Guides reference primary sources, architectural records, and on-site observations to ensure accurate storytelling for guests of all interests alike.
Tours Offered
9 tours
Curated routes across Chicago
Film Locations
Ferris Bueller & The Untouchables
See iconic movie sites
Expert Guides
Movie & Architecture
Passionate subject specialists
Typical Length
2 hours
Most tours run two hours
Reserve a spot on a 2-hour walking tour to experience film locations, secret riverfront interiors, architectural gravesites, and haunted history.
Dress in Warm Layers
Chicago winters can be chilly and windy, so wearing layers will help you stay comfortable throughout the tour.
Wear Comfortable Footwear
Expect to walk several city blocks on varied surfaces, so sturdy, comfortable shoes are a must.
Bring a Camera or Smartphone
There are plenty of festive photo opportunities along the route – don’t miss capturing the city’s holiday lights and decorations.
Book in Advance
This popular seasonal tour fills up quickly, so secure your spot early to avoid disappointment.
Warm Coat
Keeps you comfortable during chilly outdoor portions of the tour.
winter
Waterproof Boots
Useful if snow or wet conditions are present to keep your feet dry.
winter
Reusable Water Bottle
Staying hydrated is important even in cold weather during your walk.
Smartphone or Camera
Capture the festive lights and memorable moments on the tour.