Recent Searches
Clear

Top Chicago Sightseeing Cruises

Saved to wishlist!
Dates
Select Dates
Day Cruises
Day Cruises
Sunset Cruises
Sunset Cruises
Lunch Cruises
Lunch Cruises
Night Cruises
Night Cruises
Architecture Tours
Architecture Tours
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Dinner Cruises
Water Tours
Water Tours
Sailing
Sailing
City Tours
City Tours
Food Tours
Food Tours
Half-day Tours
Half-day Tours
Cruises & Sailing
Cruises & Sailing
Private Sightseeing Tours
Private Sightseeing Tours
Full-day Tours
Full-day Tours
Dining Experiences
Dining Experiences
Night Tours
Night Tours
Audio Guides
Audio Guides
Coffee Cruises
Likely To Sell Out
Likely To Sell Out
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

21 results | All Chicago Tours

Sort by: Featured

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
7052
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

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1381
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

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

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
330
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
More
  • 30 minutes
  • Free Cancellation
From
$26.16
From
$26.16

45-Minute Chicago River Architecture Tour from Magnificent Mile

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
160
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
More
  • 45 minutes
  • Free Cancellation
From
$25.00
From
$25.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
175
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Chicago Skyline Tall Ship Cruise

Chicago Skyline Tall Ship Cruise

star-4.5
189
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
More
  • 1 hour 15 minutes
From
$44.00
From
$44.00

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
159
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving 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 on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
More
  • 2 hours 30 minutes
From
$158.98
From
$158.98

Chicago Lunch Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Lunch Cruise on Lake Michigan

star-4
84
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
More
  • 2 hours
From
$81.46
From
$81.46

Chicago River Floating Tiki Bar Cruise

Chicago River Floating Tiki Bar Cruise

star-4
35
Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Fireworks Dinner Cruise with Buffet

Chicago Fireworks Dinner Cruise with Buffet

star-4
27
Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).
More
  • 3 hours
From
$158.98
From
$158.98

Chicago Premier Lake Michigan Lunch Cruise

Chicago Premier Lake Michigan Lunch Cruise

star-4
26
Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.
More
  • 2 hours
From
$90.98
From
$90.98

Chicago Premier Fireworks Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Fireworks Dinner Cruise on Lake Michigan

star-2.5
23
Set sail on Lake Michigan aboard a luxury yacht for a gourmet dinner cruise with views of the Chicago fireworks display. During the 3-hour cruise, the crew serves a 3-course plated meal with dishes prepared by your onboard chef. You can enjoy the stylish interior of the rooftop lounge, dance to DJ entertainment, or relax and soak in the views of the Chicago skyline.
More
  • 3 hours
From
$179.38
From
$179.38

Premier Chicago River Dinner Cruise
Likely to Sell OutLikely to Sell Out

Premier Chicago River Dinner Cruise

star-3.5
17
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
More
  • 3 hours
From
$172.58
From
$172.58

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
17
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
More
  • 2 hours
  • Free Cancellation
From
$427.28
per group
From
$427.28
per group

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
14
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
More
  • 2 hours
  • Free Cancellation
From
$427.28
per group
From
$427.28
per group

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

star-5
2
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.
More
  • 2 hours
  • Free Cancellation
From
$483.96
per group
From
$483.96
per group

Lake Tiki Cruise Tour in from Chicago Riverwalk to Lake Michigan

Special Offer

Lake Tiki Cruise Tour in from Chicago Riverwalk to Lake Michigan

Our flagship vessel boasts a tiki-sheik vibe, two climate controlled decks, two bars, two bathrooms, premium sound system, outdoor and indoor viewing areas. Our upscale "Admirals Lounge" features top-shelf alcohol, including the captain's private reserve. Your adventure starts on the Chicago Riverwalk when you board vessel. Enjoy a beverage as you complete the unique experience of transiting the Chicago Locks. Once on Lake Michigan take in the stunning views of Chicago's skyline.
More
  • 2 hours
  • Free Cancellation
From
$25.60
$32.00
$6.40 savings
From
$25.60
$32.00
$6.40 savings

Chicago River Fireworks Cruise

Chicago River Fireworks Cruise

See Chicago Fireworks the Island Party way. Our floating Tiki Bar offers you the unique opportunity to see the sights of the Chicago River, topped off with a fireworks show. Have questions about the buildings you'll see along the river? Our helpful staff will be happy to answer questions.
More
  • 1 hour 15 minutes to 1 hour 30 minutes
  • Free Cancellation
From
$50.00
From
$50.00

Mimosa Cruise on the Chicago River Shared Tour

Special Offer

Mimosa Cruise on the Chicago River Shared Tour

Sundays are Fun-Days aboard the floating tiki bar. See the Chicago River the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax an enjoy a beverage. Have questions about buildings? Our helpful staff will be happy to answer questions.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$28.00
$35.00
$7.00 savings
From
$28.00
$35.00
$7.00 savings

Premier Chicago River Fireworks Dinner Cruise

Premier Chicago River Fireworks Dinner Cruise

Book your passage aboard the Odyssey Chicago River ahead of time to guarantee your spot on this popular Chicago River cruise. This modern, glass-enclosed boat makes for a comfortable ride no matter the weather and gives panoramic views of Chicago’s well-known architectural gems on the banks of the river. Dig in to a 3-course plated meal while enjoying live entertainment, including fireworks displays on Wednesdays and Sundays.
More
  • 2 hours 30 minutes
From
$213.38
From
$213.38

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 Sightseeing Cruises in Chicago?
Q:
What Sightseeing Cruises in Chicago are 1 hour or less?
Q:
What Sightseeing Cruises in Chicago are taking additional safety precautions?
Q:
What Sightseeing Cruises in Chicago are good for avoiding crowds?