Find Things to Do in...
Search
Tours & Things to Do

More Great Destinations

Take time to explore tours and activities in these amazing destinations:


Shop With Confidence
  • Low Price Guarantee
  • Only Top Quality Tour and Activity Companies
  • 100% Secure Transactions
  • No Hidden Fees
  • 500,000+ Satisfied Customers
Why Book With Us
  • Save Money:

    Booking ahead will almost always save you money.

  • Save Time:

    You've got better things to do than wait in ticket lines.

  • Get The Tour You Want:

    Booking online means you get first pick of available tours.


Contact Us
Search by Category
Advanced Search

Here are your 5 search results for Holiday & Seasonal Tours in Chicago, United States

Chicago Holiday Lights Trolley and Christmas Market Tour

Chicago Holiday Lights Trolley and Christmas Market Tour - Chicago, Illinois
Star Rating

Duration: 90 minutes
Location: Chicago, Illinois

From USD
$28.00

Get into the holiday spirit with this trolley tour in Chicago! See famous landmarks such as Lincoln Park, the Magnificent Mile and Daley Plaza, all beautifully lit up with Christmas lights. Then, spend an hour at the Christkindlmarket, a German-inspired Christmas market full of vendors and family-friendly festivities ... More info ›

Get into the holiday spirit with this trolley tour in Chicago! See famous landmarks such as Lincoln Park, the Magnificent Mile and Daley Plaza, all beautifully lit up with Christmas lights. Then, spend an hour at the Christkindlmarket, a German-inspired Christmas market full of vendors and family-friendly festivities.

Meet at the Palmer House Hotel in the evening and hop on the trolley for a 1.5-hour trip around Chicago. You’ll be amazed by the dazzling display of Christmas lights and decorations as you pass famous landmarks such as Lincoln Park and the Magnificent Mile.

Cruise down Wacker Street along the Chicago River, spot the famous Daley Plaza Christmas tree, and admire the illuminated high-rise buildings around Lake Shore Drive. Along the way, your guide will provide informative commentary about the sites you see and teach you a bit about Chicago’s culture and history.

After your trolley tour, hop off and spend an hour at Christkindlmarket, a German-inspired Christmas market located at Daley Plaza in downtown.

Here, you’ll find local and international vendors and enjoy festive music and family-friendly activities such as scavenger hunts. This is the perfect place to snag a last-minute Christmas gift! You’ll be taken back to the Palmer House Hotel after your tour.

Less info

Chicago Architecture Walking Tour at Night: Summer Lights and Fireworks

Chicago Architecture Walking Tour at Night: Summer Lights and Fireworks - Chicago, Illinois
Star Rating

Duration: 2 hours
Location: Chicago, Illinois

From USD
$25.00

On this 'architecture lite' tour, you visit the most beloved spots in downtown Chicago during this enchanting stroll. You will stay very close to Lake Michigan, weaving your way through secret spots that one can only discover on foot, as you make your way to the absolute best view of Chicago ... More info ›

On this 'architecture lite' tour, you visit the most beloved spots in downtown Chicago during this enchanting stroll. You will stay very close to Lake Michigan, weaving your way through secret spots that one can only discover on foot, as you make your way to the absolute best view of Chicago.  Bring your cameras as this is one place you'll want to capture the view!  

Please note, this tour is 'architecture lite.' Rather than learning a ton of information about architecture and history, this tour is meant for the simple enjoyment of the city's prettiest spots at night. You won't find a boat, a bus, or even a segway on this tour. Come and take an evening walk with us.

On this special summertime tour, you will have the chance to slow down from your day and experience the elegant beauty of the city at night. You will enjoy both well-known and secret gardens located just mere blocks away from the Magnificent Mile. At the end of this tour, you will take in the fireworks show at Navy Pier from a secret viewing spot. This tour allows you to see the best view of the Chicago skyline at night and much more.

This tour is slightly longer than regular routes, lasting for about 2 hours and covering 2.5 miles. You'll arrive at the fireworks viewing spot by 9:30pm.

Less info

Chicago Holiday Lights Tour

Chicago Holiday Lights Tour - Chicago, Illinois
Star Rating

Duration: 2 hours 30 minutes
Location: Chicago, Illinois

From USD
$28.00

Celebrate the holiday season with a Chicago Christmas lights tour! The 90-minute tour in a heated motor coach takes you around downtown Chicago to see the sights and festive holiday lights. Along the way, enjoy a stop at the famous Christkindlmarket for a spot of shopping and tasting of traditional German delicacies.

The Chicago Holiday Lights Tour takes you through the brightly decorated streets of Chicago ... More info ›

Celebrate the holiday season with a Chicago Christmas lights tour! The 90-minute tour in a heated motor coach takes you around downtown Chicago to see the sights and festive holiday lights. Along the way, enjoy a stop at the famous Christkindlmarket for a spot of shopping and tasting of traditional German delicacies.

The Chicago Holiday Lights Tour takes you through the brightly decorated streets of Chicago. Join in the city's festive atmosphere and be caught up in the holiday spirit of Christmas!

Your Holiday Lights Tour includes a 1-hour stop at the popular German Christkindlmarket in downtown Chicago's Daley Plaza. Here, you will find an array of German handicrafts including nutcrackers, cuckoo clocks, beer steins, and Hummel figurines as well as a large assortment of savory and sweet foods, drinks and candied treats. You won't be able to resist the tempting aromas of sizzling sausages, sauerkraut, potato pancakes, waffles and other delicacies wafting through the market.

Less info

Chicago New Year's Eve Luxury Dinner Cruise

Chicago New Year's Eve Luxury Dinner Cruise - Chicago, Illinois

Duration: 3 hours
Location: Chicago, Illinois

From USD
$311.16

Take a 3 hour gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan ... More info ›

Take a 3 hour gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right onboard. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks such as the Willis (formerly Sears) Tower and John Hancock building, plus musical entertainment provided by the onboard DJ.

Spend an exceptional evening cruising the shoreline of Chicago onboard a luxury yacht, admiring the city’s striking architecture as you enjoy a gourmet, 3-course dinner. It’s the perfect way to spend a festive evening living it up with friends, family, or that special someone during your time in Chicago.

Make your way to Navy Pier on the evening of your cruise, making sure to dress to impress for this festive evening. As you make your way through this famous entertainment complex, enjoy the bustling mix of pedestrians, street performers, and lakeshore views found at this famous pier.

Then step onboard your yacht to begin your unforgettable evening. You’ll have your picture taken by the ship photographer to help capture the moment. Then follow your host as you’re whisked to your table for your meal. The servers will introduce themselves and offer you the chance to decide how you’d like them to pace your meal.

Musical entertainment is provided by the onboard DJ, who will keep things lively with a mix that covers everything from classic jazz to more contemporary hits.

When you have a few moments, make sure to explore the ship’s luxurious design and amenities. Ranging from the temperature-controlled dining area to the observation deck, you’re sure to notice the vessel’s attention to detail and unique art-deco interior accents, most of which pay homage to the classic ocean liners of yesteryear. Make sure to also stop by the Captain’s bridge, an area that’s open to all guests for the majority of the cruise.

Less info

Booking.com

Chicago New Year's Eve Dinner Cruise with Buffet

Chicago New Year's Eve Dinner Cruise with Buffet - Chicago, Illinois

Duration: 3 hours
Location: Chicago, Illinois

From USD
$229.71

End the year with a bang when the sky lights up at midnight! Make your evening in Chicago one to remember with this 3-hour cruise featuring dinner, sightseeing, and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain, and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet ... More info ›

End the year with a bang when the sky lights up at midnight! Make your evening in Chicago one to remember with this 3-hour cruise featuring dinner, sightseeing, and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain, and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ, who will mix up a selection of dance favorites.

Make your way to Navy Pier, where boarding begins at 8:30pm for a 9:30pm departure. You'll dance, dine, and celebrate during this beautiful 3-hour cruise along the shores of Lake Michigan, enjoying amazing Windy City skyline views along the way.

Enjoy a few drinks (own expense) as you cruise, then sit down to an all-you-can-eat buffet that includes salads, pastas, gourmet entrees from a carving station, and an amazing spread of desserts. 

Following the meal, head to the dance floor to join a top DJ for the evening's party, grooving with the backdrop of the Chicago skyline. This 3-hour cruise concludes at the original departure point. 

Less info