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12 results | All Chicago Tours

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Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
215
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Likely to Sell OutLikely to Sell Out

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.
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  • 2 hours
  • Free Cancellation
From
USD427.28
per group
From
USD427.28
per group

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
7509
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).
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
1636
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Chicago Signature Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Signature Dinner Cruise on Lake Michigan

star-4
141
Make your evening in Chicago one to remember with this luxury sunset 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.
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  • 3 hours
From
USD122.80
From
USD122.80

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

Chicago Lunch Cruise on Lake Michigan

star-4
94
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.
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  • 2 hours
From
USD81.82
From
USD81.82

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
349
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.
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  • 40 minutes
  • Free Cancellation
From
USD28.34
From
USD28.34

Chicago Fireworks Dinner Cruise with Buffet
Likely to Sell OutLikely to Sell Out

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).
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  • 3 hours
From
USD158.98
From
USD158.98

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
616
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
Likely to Sell OutLikely to Sell Out

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
197
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. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD49.00
From
USD49.00

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
168
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.
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  • 2 hours 30 minutes
From
USD180.18
From
USD180.18

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
617
Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.
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  • 1 hour 30 minutes
From
USD56.00
From
USD56.00

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What people are saying about Sunset Cruises in Chicago

star-5
Chicago Sunset Cruise
"the views and experiencing it with friends :) the pictures I took are so gorgeous and I hope to return again"..."
star-5
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
"Highly recommend the sunset cruise. What a great way to view Chicago’s skyline! Friendly, informative Captain helped us decide on must see spots for the rest of our stay. Thank you."..."
star-5
Chicago Architecture River Cruise
"The narration provided enhanced the view of each building. The weather was also great. Would recommend this trip to a visitor to Chicago"..."
star-5
90-Minute Chicago River Architecture Tour
"Excellent tour! We loved our guide, Kay. She was fun, entertaining, and informative! I learned a lot more than I expected about the architecture of Chicago. I highly recommend this tour!"..."
star-5
Chicago Signature Dinner Cruise on Lake Michigan
"Had a fun filled dinner cruise great food and music. Nice size dance floor. Great upper and lower deck experience."..."
star-5
Chicago Lunch Cruise on Lake Michigan
"It was an amazing experience would definitely do again. The food was amazing the energy was music the was good as well"..."
star-5
Lake Michigan Sightseeing Cruise
"Good Overall Experience. The crew members were really friendly and helpful. One of them even offered to take our pictures, that was so thoughtful. Nice views of the Chicago skyline."..."
star-5
Chicago Fireworks Dinner Cruise with Buffet
"Delightful dinner, still saw fireworks despite the rain. Great music and atmosphere. We would definitely do again and recommend it to couples and families."..."
star-5
Chicago Lake and River Architecture Tour
"Kenneth was amazing. Highly recommend his chores. Extremely knowledgeable, articulate, entertaining, personable, and more. I would do this exact trip again and again."..."
star-5
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
"The crew were engaging and made certain safety was practiced. The history lesson was great… but a megaphone would have been a great asset in order to hear everything. Great trip that all must go on while in Chicago!"..."
star-5
Chicago Premier Dinner Cruise on Lake Michigan
"Great time with my wife and friends. Wonderful views of Chicago. If your not expecting the Ritz you will enjoy it."..."
star-5
Chicago Architecture Center River Cruise aboard Chicago's First Lady
"Learning so much I had never known before about the city’s unique experience with architectural creativity, while weaving around the city. Simply marvelous."..."

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 Sunset Cruises in Chicago?
Q:
What Sunset Cruises in Chicago are taking additional safety precautions?
Q:
What Sunset Cruises in Chicago are good for avoiding crowds?
A:
These hidden gems in Chicago may have limited interaction with crowds: