Recent Searches
Clear

Top Chicago Seasonal & Special Occasions

Saved to wishlist!
Dates
Select Dates
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Seasonal
Holidays
Holidays
Christmas
Christmas
Walking Tours
Walking Tours
Private and Luxury
Private and Luxury
City Tours
City Tours
Half-day Tours
Half-day Tours
Private Sightseeing Tours
Private Sightseeing Tours
Bus Tours
Bus Tours
Kid-Friendly
Segway Tours
Segway Tours
Summer
Summer
Luxury Car Tours
Luxury Car Tours
Honeymoon
Honeymoon
Water Tours
Water Tours
Sightseeing Cruises
Sightseeing Cruises
Day Cruises
Day Cruises
Museum Tickets & Passes
Museum Tickets & Passes
Historical Tours
Historical Tours
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

17 results | All Chicago Tours

Sort by: Featured

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7010
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
More
  • 1 hour
  • Free Cancellation
From
$40.33
From
$40.33

Chicago CityPASS

Chicago CityPASS

star-4.5
335
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
More
  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
150
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
More
  • 2 hours
  • Free Cancellation
From
$73.24
From
$73.24

Amazing Lakefront Segway Tour in Chicago

Amazing Lakefront Segway Tour in Chicago

star-4.5
67
Experience Chicago like never before on this guided, 2.5-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain, with the Windy City skyline as the backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Adler Planetarium and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toe shoes.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$75.00
From
$75.00

Chicago Spray Paint 'n' Sip at Studio W.I.P.- BYOB

Chicago Spray Paint 'n' Sip at Studio W.I.P.- BYOB

star-5
74
Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Pick from multiple class times, and make your own way to the Chicago studio. You’ll learn different styles and techniques from your instructors (including guest artists), can try out stenciling and spray-painting, and can even create your own work of art on canvas to bring home at the end of class.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

2-Hour Chicago Fireworks Segway Tour

2-Hour Chicago Fireworks Segway Tour

star-5
24
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1363
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
151
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
More
  • 4 hours
  • Free Cancellation
From
$26.00
From
$26.00

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
562
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
218
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
More
  • 60 days
From
$59.00
From
$59.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
297
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
More
  • 3 hours
  • Free Cancellation
From
$69.99
From
$69.99

Holiday Hike Chicago-Style: Festive Food & Walking tour

Holiday Hike Chicago-Style: Festive Food & Walking tour

star-5
15
Stroll through Chicago's winter streets, lit up for the holidays, 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. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
More
  • 3 hours
  • Free Cancellation
From
$69.99
From
$69.99

2-Hour Chicago Holiday Lights Segway Tour

2-Hour Chicago Holiday Lights Segway Tour

star-4.5
11
Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive department store displays. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.
More
  • 2 hours to 2 hours 15 minutes
  • Free Cancellation
From
$75.10
From
$75.10

The Christmas Tree Crawl Experience Chicago at the Holidays

The Christmas Tree Crawl Experience Chicago at the Holidays

star-5
7
Experience the vibrant life of downtown Chicago at its most exciting and beautiful time of year! Visit stops like the Christkindlmarkt, the old Marshall Field's, the Palmer House Hilton Historic Lobby, Millennium Park, and more!
More
  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

star-5
1
There’s nothing more magical than downtown Chicago during the holiday season. 2-hour guided walking tour through the Chicago Loop, Millennium Park and the Magnificent Mile. This tour is brought to you, internationally recognized tour company headquartered right here in Chicago. Our entertaining guides will get your holiday spirit primed with plenty of fun facts, general knowledge, and the best of Chicago holiday decor. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the fabulous Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. This tour is a walking tour only. No food/drinks on this particular tour.
More
  • 2 hours
  • Free Cancellation
From
$29.99
From
$29.99

Magnificent Mile Holiday Lights Walking Tour

Magnificent Mile Holiday Lights Walking Tour

Catch the holiday spirit in Chicago! Get your best walking shoes on and join us for an adventure through the beautifully illuminated downtown Chicago. Your holiday journey will start at Chicago’s front yard, Millenium Park, and is just steps away from Macy’s festive windows. Enjoy the delicious tastes that Christkindlmarket Chicago has to offer. During this stroll, we cross over the Riverwalk and onto the Magnificent Mile surrounded by lights and spectacular views along the way. The tour ends with hot chocolate by Mariano Park. This tour is full of the holiday spirit and everyone is welcome. (Tour departs from Bike & Roll, 34 S. Michigan Avenue at Monroe Street)
More
  • 2 hours
  • Free Cancellation
From
$59.00
From
$59.00

Chicago Elopement! City Landmark Photoshoot, Private Driver, and More!

Chicago Elopement! City Landmark Photoshoot, Private Driver, and More!

Chicago Elopement Package! What a way to say, "I Do." Chicago is a city full of great architecture and beautiful waterways, which make the best wedding photo backdrops. Your wedding coordinator will walk you through the paperwork process and help you pick a location in one of our city's most picturesque parks (if you want an indoor location, this can also be arranged at a minimal fee.) Once your ceremony is finished, a private driver will be whisk you away you up and take you around the city to capture some wedding day photos with some of Chicago's most iconic landmarks. ***Please note: After you book, we will schedule a phone call within 7 days. If at this point, you do not feel this is the right fit, I will refund you 100%....no questions asked.***** email us for more details.
More
  • 2 to 3 hours
From
$1,900.00
per group
From
$1,900.00
per group

Filters

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Seasonal & Special Occasions in Chicago?
Q:
What Seasonal & Special Occasions in Chicago are taking additional safety precautions?
Q:
What Seasonal & Special Occasions in Chicago are good for avoiding crowds?