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18 Chicago Day Cruises

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
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 the Aon Center, 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
  • Free Cancellation
From  
US$41.44
From  
US$41.44
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  • 1 hour
  • Free Cancellation

Chicago River Architecture Tour

Chicago River Architecture Tour

star-5
Discover the architectural gems of the Windy City from an ideal vantage point on a leisurely 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 15 minutes
  • Free Cancellation
From  
US$39.00
From  
US$39.00
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  • 1 hour 15 minutes
  • Free Cancellation

Chicago Architectural River Cruise

Chicago Architectural River Cruise

star-4.5
See the towers, piers and iconic landmarks along the Chicago River on an architectural tour through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$49.28
From  
US$49.28
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  • 1 hour 30 minutes
  • Free Cancellation

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
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  
US$39.00
From  
US$39.00
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  • 1 hour 30 minutes
  • Free Cancellation

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus with a small group of twelve people or less. This ensures an intimate touring experience as you enjoy downtown and some North side neighborhoods. You will have a chance to get out and visit several locations such as the 1888 skyscraper called The Rookery, with its Frank Lloyd Wright designed lobby and the unparalleled skyline views from Museum Campus. Listen as your guide talks about the historical and cultural factors that make Chicago unique. The city tour ends at Millennium Park, home of the famous Cloud Gate sculpture, commonly referred to as "the bean."  Opt to upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture. Pick-ups from most downtown Chicago hotels are included.
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  • 2 hours
  • Free Cancellation
From  
US$37.50
From  
US$37.50
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  • 2 hours
  • Free Cancellation

Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady

star-5
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
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  • 1 hour 30 minutes
From  
US$47.00
From  
US$47.00
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  • 1 hour 30 minutes

Chicago River Boat Architecture Tour

Chicago River Boat Architecture Tour

star-5
Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago. Tour departures from 465 N. McClurg Ct.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$49.28
From  
US$49.28
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  • 1 hour 30 minutes
  • Free Cancellation

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
Take in superlative-worthy views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's iconic 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.Please note: This cruise is only 30 minutes during fall and winter
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  • 30 minutes
  • Free Cancellation
From  
US$25.76
From  
US$25.76
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  • 30 minutes
  • Free Cancellation

Chicago Odyssey Lake Michigan Lunch Cruise

Chicago Odyssey Lake Michigan Lunch Cruise

star-4
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.
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  • 2 hours
From  
US$88.26
From  
US$88.26
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  • 2 hours

Spirit of Chicago Fireworks Dinner Cruise with Buffet

Spirit of Chicago Fireworks Dinner Cruise with Buffet

star-4.5
Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while you dine on a lavish, all-you-can-eat buffet! See spectacular views of the Chicago skyline and a live DJ spinning your favorite songs. In the summer months, enjoy a breathtaking fireworks display.
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  • 3 hours
  • Free Cancellation
From  
US$156.26
From  
US$156.26
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  • 3 hours
  • Free Cancellation

Private Sunset Sail on Lake Michigan in Chicago

Private Sunset Sail on Lake Michigan in Chicago

star-5
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  
US$439.04
From  
US$439.04
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  • 2 hours
  • Free Cancellation

Private Sailing Trip on Lake Michigan in Chicago

Private Sailing Trip on Lake Michigan in Chicago

star-5
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.
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  • 2 hours
  • Free Cancellation
From  
US$439.04
From  
US$439.04
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  • 2 hours
  • Free Cancellation

Chicago Land and River Architecture Tour: North and South Shores

Chicago Land and River Architecture Tour: North and South Shores

star-4.5
Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$92.95
From  
US$92.95
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  • 3 hours 30 minutes
  • Free Cancellation

Odyssey Chicago River Architectural Lunch Cruise

Odyssey Chicago River Architectural Lunch Cruise

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.
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  • 2 hours
  • Free Cancellation
From  
US$101.86
From  
US$101.86
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  • 2 hours
  • Free Cancellation

Private Navy Pier Fireworks Sail on Lake Michigan in Chicago

Private Navy Pier Fireworks Sail on Lake Michigan in Chicago

star-5
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.
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  • 2 hours
  • Free Cancellation
From  
US$497.28
From  
US$497.28
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  • 2 hours
  • Free Cancellation

Chicago Land and River Architecture Tour: Historic South Side

Chicago Land and River Architecture Tour: Historic South Side

star-4
See the architecture of Chicago's South Side by both land and on a Chicago River boat tour. Traveling south of the Loop along Michigan Avenue and South Lake Shore Drive, you'll pass by sights such as the Art Institute of Chicago, University of Chicago, Jackson Park, the Museum of Science and Industry, Museum Campus, Buckingham Fountain, and former President Obama's home.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$73.95
From  
US$73.95
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  • 3 hours 30 minutes
  • Free Cancellation

Semi-Private Shared Sailing Trip on Lake Michigan in Chicago

Semi-Private Shared Sailing Trip on Lake Michigan in Chicago

Want to get away from the crowds and see the BEST views of the Chicago? Then you need to come sailing and experience Chicago from the water!Join us for this TWO-HOUR, SEMI-PRIVATE, SHARED SAILING TRIP on Lake Michigan where we’ll sail along the lakefront and take in Chicago’s spectacular skyline.Our SEMI-PRIVATE, SHARED SAILING TRIPS allow a more engaging and personal sailing experience than that of a huge dinner cruise or tour boat filled with strangers. Yes, you may be sailing with a few people that you don’t know. That’s the SHARED part of it. But with a maximum capacity of ONLY 6 passengers, our sailboats provide a more intimate setting. On our sailboats you’re free to engage the captain in casual conversation and even take part in the actual sailing if you so desire. Rest assured, our professional captains will always be there to ensure a safe and enjoy sailing experience for all.Come Sailing - Chicago’s Premier Sailing Experience and Private Sailing Charter
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  • 2 hours
  • Free Cancellation
From  
US$109.76
From  
US$109.76
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  • 2 hours
  • Free Cancellation

Chicago River Experience

Chicago River Experience

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours.
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  • 45 minutes
  • Free Cancellation
From  
US$21.00
From  
US$21.00
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  • 45 minutes
  • Free Cancellation


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