Top 10 Seasonal in Chicago

Destination: Chicago.
Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling, the "Great Tree" in the Walnut Room and the store’s decorated holiday windows. We return to the Pedway and follow it to Civic Center Plaza for a visit to the Christkindlmarket, an authentic European holiday market. We return to the Pedway for a visit to City Hall followed by a short walk to a nearby L station. A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and Millennium Park to view the famous Cloud Gate sculpture, aka, The Bean and the city's holiday tree .
Known For: Chicago Private and Luxury, Chicago Walking Tours, Chicago Likely To Sell Out, Chicago Half-day Tours, Chicago Christmas, Chicago Cultural Tours, Chicago Small Group, Chicago Likely to Sell Out, Chicago Seasonal, Chicago Excellent Quality, Chicago Historical Tours.
Duration: Around 3 hours.

Destination: Chicago.
Learn the history that makes the Chicago River and its recently updated Riverwalk historically unique.   Chicago is home to one of the world’s most recognizable and celebrated skylines and the Riverwalk’s intimate vantage provides an ideal perspective from which to learn and appreciate its incredible buildings.Discover Chicago's Rich History and Iconic Architecture Experience the vibrant tapestry of Chicago’s past and present with our Chicago Riverwalk Tour. Perfect for history buffs, architecture enthusiasts, and curious visitors, this 2-hour guided tour uncovers fascinating stories and architectural marvels that define the Windy City.
Known For: Chicago Likely to Sell Out, Chicago Likely To Sell Out, Chicago Walking Tours, Chicago Private and Luxury, Chicago Seasonal, Chicago Cultural Tours, Chicago New Product, Chicago Historical Tours.
Duration: Around 2 hours.

Destination: Chicago.
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.
Known For: Chicago Water Tours, Chicago Seasonal, Chicago Sightseeing Cruises, Chicago Day Cruises, Chicago Historical Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.
Known For: Chicago City Tours, Chicago Seasonal, Chicago Walking Tours, Chicago National Holidays, Chicago Christmas.
Duration: Around 2 hours.

Destination: Chicago.
Skip the crowds—this is a private tour for your group only! “Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Begin your tour at 875 North Michigan Avenue (formerly the John Hancock Center), adorned with holiday decorations and offering spectacular views of the city’s festive lights. Stroll down N State St, a vibrant street bustling with holiday shoppers and seasonal displays. Conclude your tour at Christkindlmarket Chicago, a traditional German holiday market filled with crafts, food, and the spirit of Christmas—an authentic and memorable way to experience the joy of a Chicago Christmas. Itineraries are subject to change based on availability.
Known For: Chicago Seasonal, Chicago Christmas, Chicago Walking Tours, Chicago Likely to Sell Out, Chicago Likely To Sell Out, Chicago Private Sightseeing Tours, Chicago Cultural Tours.
Duration: Around 2 hours.

Destination: Chicago.
S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely cruising, this charter allows you to set your own schedule and enjoy a personalized experience. With a minimum rental of three hours, you can relax on board while exploring beautiful coastal views. Captain's fees are separate, ensuring a tailored experience for your group. - Exclusive yacht rental for luxury experiences - Flexible scheduling with afternoon and evening options - Minimum three-hour rental for ample exploration - Personalized service with optional captain at an additional fee
Known For: Chicago Boat Rentals, Chicago Water Equipment Rentals, Chicago Self-guided Tours, Chicago Seasonal, Chicago New Product, Chicago Rentals.

Destination: Chicago.
See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night while gliding through the park & lakefront on a Segway PT. View Buckingham Fountain's romantic evening light show with the illuminated skyline as a backdrop. This evening fireworks tour glides along the lakefront to our secret spot for watching Navy Pier's Fireworks display. It's difficult to decide which is more spectacular — the fireworks or the Chicago skyline in its evening splendor! A perfect family activity, this is one of our most fabulous Chicago Segway tours.
Known For: Chicago Private and Luxury, Chicago City Tours, Chicago Seasonal, Chicago Segway Tours, Chicago Fireworks Shows.
Duration: Around 2 hours.

Destination: Chicago.
One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!
Known For: Chicago Comedy Shows, Chicago Seasonal, Chicago Food & Drink, Chicago Theater Shows, Chicago Shows, Chicago Adults-only Shows, Chicago Weddings & Celebrations.
Duration: Around 1 hour and a half.

Destination: Chicago.
Discover the heart of Chicago on this guided walking tour led by a knowledgeable local. Begin in Millennium Park, home to the iconic Cloud Gate (“The Bean”), where art, architecture, and green space come together. Explore hidden sections of the Chicago Pedway, then stroll along the scenic Chicago Riverwalk for stunning skyline views. Continue along the Magnificent Mile, passing architectural icons like the Wrigley Building and Tribune Tower, and cross the historic Michigan Avenue Bridge. Along the way, learn about the Great Chicago Fire, the city’s architectural legacy, and modern culture. The tour concludes near the Starbucks Reserve Roastery, with free time to explore or enjoy a classic Chicago savory treat (optional, at your own expense). Perfect for first-time visitors looking to experience Chicago’s history, architecture, and local flavor in a relaxed, small-group setting.
Known For: Chicago Likely to Sell Out, Chicago Small Group, Chicago Likely To Sell Out, Chicago Walking Tours, Chicago Private and Luxury, Chicago City Tours, Chicago Seasonal, Chicago New Product, Chicago Historical Tours.
Duration: Around 2 hours and a half.

Destination: Chicago.
Immerse yourself in the vibrant flavors of Mexico with a hands-on cooking class at Su Casa Mexican Restaurant. Guided by experienced chefs, participants will learn the art of crafting authentic tamales and tacos from scratch. This class is tailored for all skill levels, making it an ideal setting for food enthusiasts eager to enhance their culinary repertoire. As you knead, roll, and fill your creations, anticipate the rewarding moment of tasting your delicious handiwork, complemented by chips, salsa, and a refreshing drink.
Known For: Chicago Seasonal, Chicago Food & Drink, Chicago Cooking Classes.
Duration: Around 2 hours.