Chicago: Guided Holiday Food & Walking Tour of Festive Sites｜United States

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.