Highlights
- VIP Christkindlmarket access with hot cider and time to shop festive stalls.
- See top holiday landmarks: Millennium Park ice rink, City Tree, Mag Mile lights
- Taste it all—deep dish, hot dogs, Italian beef, brownie, popcorn, and hot cider.
- Friendly expert guides share Chicago holiday stories and seasonal traditions.
- Chicago’s signature eats included—enough delicious bites to be a full holiday meal.
Description
From shimmering lights to decadent bites, Christmas in Chicago is pure magic — and this Chicago Food Tour brings it all together in one unforgettable experience. This walking tour blends iconic holiday sights with mouthwatering local eats, making it one of the Best Things to Do in Chicago During the Holidays.
We’ll guide you through the Loop’s top seasonal landmarks: see the City’s official Christmas tree and ice rink at Millennium Park, stroll past Macy’s legendary holiday window displays, and take in the twinkling lights on State Street. You’ll also skip the crowds with VIP access to Christkindlmarket, Chicago’s beloved open-air holiday market. Warm up with a cup of hot apple cider as you browse handcrafted gifts and traditional holiday goods from around the world.
This isn’t just sightseeing — it’s also a taste of Chicago’s most iconic flavors. You’ll bite into a deep-dish pizza with a buttery crust, rich tomato sauce, and bubbling mozzarella. You’ll try a true Chicago-style hot dog, topped with relish, onions, tomatoes, mustard, sport peppers, and that classic dill pickle spear — all tucked into a poppy seed bun (and yes, absolutely no ketchup). We also include a classic Italian beef sandwich — thinly sliced, seasoned just right, and dipped in its own savory juices, just like a true Chicago joint would serve it. Add in the sweet-and-salty perfection of Garrett’s Chicago Mix popcorn and a chewy, chocolatey original-recipe brownie from the historic Palmer House Hotel, where the brownie was first invented — and you’ve got yourself a real taste of the city.
As we head toward the Magnificent Mile, you’ll learn about one of Chicago’s proudest holiday traditions — the Magnificent Mile Lights Festival. This isn’t just twinkle lights on trees — it’s a full-on kickoff celebration for the season, with a parade led by Mickey and Minnie Mouse, live music, and over a million lights illuminating Michigan Avenue. It officially marks the start of holiday shopping season for the city, and you’ll see firsthand how this stretch of shops and skyscrapers turns into a winter wonderland.
Want to toast to the season? Upon arrival, you’ll have the option to upgrade with a VIP Christmas adult beverage tasting ($19.99/person), featuring festive drinks like local seasonal brews.
This tour combines Chicago’s rich food culture with its most beloved holiday traditions — perfect for visitors and locals alike looking to celebrate the season in style. Make it your new holiday tradition and jumpstart your Christmas spirit the Chicago way.
Includes
VIP entrance to Christkindlmarket with warm apple cider & time to explore festive stalls
Holiday walking & food tour featuring 5 classic tastings—enough to fill you up with cheer
Stroll past the Millennium Park Ice Rink, City Christmas Tree, Cloud Gate, the Loop, Macy’s Christmas display, State Street, Chicago Theater & Magnificent Mile holiday lights
A slice of legendary deep-dish pizza, baked golden with gooey cheese and holiday joy
A classic Chicago-style hot dog, decked out with all the iconic toppings—no ketchup allowed!
Savory Italian beef sandwich, dipped in warm au jus and topped with spicy or sweet peppers
Original-recipe brownie—rich, chocolatey, & born right here in Chicago’s holiday heart
Garrett’s famous Chicago Mix popcorn—a crave-worthy combo of caramel & cheddar magic
Optional craft beer upgrade (3 local brews, just $19.99 at check-in)
Led by a certified local guide who shares Chicago’s holiday history, food, & festive spirit
Excludes
Gratuity for guide
Upon Arrival you will have the option to upgrade to a VIP adult drink package which includes 3 unique beverage pairings. This option is $19.99/per person (adults only)
Important Information
- Arrive 15 minutes early for check-in
Tour runs rain, snow, or shine
Walking pace is relaxed & suitable for all fitness levels
Tastings are generous—enough for a full lunch or dinner
Please notify us in advance of any dietary needs
A 15% cash tip for your guide is suggested (no ATM on-site)
Samples include Deep Dish pizza, Chicago-style hot dog, Italian beef, original brownie, Garrett’s Chicago mix popcorn, and hot apple cider (*items may change)
Upon Arrival you will have the option to upgrade to a VIP adult drink package which includes 3 unique beverage pairings. This option is $19.99/per person (adults only)
Easy cancellation
Cancel up to 24 hours in advance for a full refund
