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20 results | All Chicago Tours

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

star-4.5
196
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’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy
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Chicago’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy

star-4.5
40
Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
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  • 2 hours
  • Free Cancellation
From
USD99.00
From
USD99.00

Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
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Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner

star-4.5
38
Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD39.00
From
USD39.00

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
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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.
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  • 2 hours
  • Free Cancellation
From
USD427.28
per group
From
USD427.28
per group

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
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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
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Chicago Architecture River Cruise

star-5
7451
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
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90-Minute Chicago River Architecture Tour

star-4.5
1614
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 Lunch Cruise on Lake Michigan
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Chicago Lunch Cruise on Lake Michigan

star-4
89
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
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Lake Michigan Sightseeing Cruise

star-4.5
346
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 Lake and River Architecture Tour
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Chicago Lake and River Architecture Tour

star-4.5
607
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

Chicago Sunset Cruise
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Chicago Sunset Cruise

star-4.5
204
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

Chicago Premier Lake Michigan Lunch Cruise

Chicago Premier Lake Michigan Lunch Cruise

star-4
27
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
USD98.22
From
USD98.22

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2442
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

30 Minute Lake Michigan Speedboat Ride
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30 Minute Lake Michigan Speedboat Ride

star-4.5
126
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
From
USD34.75
From
USD34.75

Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier

Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier

star-4.5
12
Watch Navy Pier's fireworks display from the deck of a sailboat. During this 75-minute cruise on Lake Michigan, get views of the Chicago city skyline lit up at night and the colorful fireworks exploding over the lake. Listen to your guide's commentary about the city's history and join in on some traditional shipboard working songs if you like.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD79.00
From
USD79.00

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.
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  • 2 hours
  • Free Cancellation
From
USD483.96
per group
From
USD483.96
per group

4th of July Fireworks! Aboard Chicago's Official Tall Ship Windy!

4th of July Fireworks! Aboard Chicago's Official Tall Ship Windy!

star-5
1
See the sights of Chicago from the water during a 90-minute tall ship sailing tour on Lake Michigan. Sip a complimentary drink as you soak in views of landmarks along the waterfront and the Great Lakes. It's the perfect way to experience the Windy City from a new perspective.
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  • 2 hours
  • Free Cancellation
From
USD139.00
From
USD139.00

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
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Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

You will be treated to a morning of relaxation and fun on Lake Michigan on this sailboat charter. You are in charge of the itinerary, guest list, even music choices! There is a fridge and ice aboard if you would like to bring refreshments (no glass please) and if you are feeling adventurous, you can take a turn at the helm.
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  • 2 hours
  • Free Cancellation
From
USD433.82
per group
From
USD433.82
per group

Chicago's Sail Grand Prix June 18-19 at Navy Pier. VIP Event Limited Tickets

Chicago's Sail Grand Prix June 18-19 at Navy Pier. VIP Event Limited Tickets

On June 18 and 19 2022 ten national teams will race cutting-edge, foiling F50 catamarans – capable of speeds in excess of 100 kph – along the shores of Lake Michigan in front of the Chicago skyline. Mark you calendars this Father’s Day weekend for two-days of speed, drama, and thrills as the entire city kicks off Summer 2022 at Navy Pier! Race times are at 3pm to 4:30pm both days. For a limited number of VIP guests, you can watch Sail Grand Prix aboard Chicago’s Official 148′ Flagship “Windy”. For this special event, Windy will depart Navy Pier at 2pm for a premium viewing area on Lake Michigan. Windy will return by 4:45pm.
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  • 2 hours 30 minutes
  • Free Cancellation
From
USD129.00
From
USD129.00

Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise

Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise

Experience the Air & Water Show Aboard 148' Tall Ship Windy. This is a VIP Charter - Truly the Best Seat in Chicago. Leave our dock and motor to center stage for the best viewing of the Air & Water Show. A don’t miss experience. Chicago’s famous Air and Water Show aboard the Tall Ship Windy is truly a magical event. While the official schedule has yet to be announced, it’s anticipated that the US Navy Blue Angels will return again in 2022 to wow audiences — along with appearances by the USAF F-35A Lightning II Demo, Michael Goulian in his acrobatic Extra 330SC, Rob Holland in the MXS-RH, Susan Dacy in her Super Stearman “Big Red”, and antique military aircraft from the Warbird Heritage Foundation. Also watch for the US Army Golden Knights parachute teams, the U.S. Navy Leap Frogs parachute team, as well as other crowd-pleasing stunts by the AeroShell Aerobatic Team, and a performance by the Chicago Fire Department Air/Sea Rescue team.
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  • 3 hours
  • Free Cancellation
From
USD139.00
From
USD139.00

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What people are saying about Sailing in Chicago

star-5
Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
"The bots in amazing shape and the crew simply first rate. What an awesome tour of the cityscape and being out in Lake Michigan under the sails was just a thrill. Hoisting the sails and super interesting pirate stories were just an added perk. Highly recommend this trip and will do it again!"..."
star-5
Chicago’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy
"Awesome story telling and cruise. This was my first time on lake michigan and also first time on a sailboat."..."
star-5
Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner
"Had a blast! Not cheesy at all. Lots of great information, friendly crew, and beautiful views of the city!"..."
star-5
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
"Mike was excellent, the boat was large, immaculate and well maintained. Wind was great and we all enjoyed the sail."..."
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
"Great excursion! We enjoyed the history of Chicago and the variety of the architecture. Highly recommend!"..."
star-5
90-Minute Chicago River Architecture Tour
"Loved it. Must do for sure, it’s a tour you will gain lot of knowledge, wonderful views n have a great time. Must do if you are with family for sure."..."
star-5
Chicago Lunch Cruise on Lake Michigan
"We loved it. We went as part of our 1 yr anniversary. It was nice and nice weather in Chicago. The water was pretty. Lovely"..."
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 Lake and River Architecture Tour
"time with family in a great city, good weather, we wanted to go around sunset so this was close enough"..."
star-5
Chicago Sunset Cruise
"The tour guide and the views, the lock was very exciting and seeing the view of Chicago at sunset was beautiful."..."
star-5
Chicago Premier Lake Michigan Lunch Cruise
"Awesome staff, Natalie did amazing. I asked if she could put on a song for my boyfriend and I and she did even though I know we aren’t allowed to dance she did! It was a great time and will definitely do again. Thanks Natalie!"..."
star-5
Gangsters and Ghosts Tour in Chicago
"I did this tour as a solo. Andre did great from the beginning. From the moment he introduced himself and gave a history of my last name, charming to say the least. I won't spoil the tour but the history and sights are the very best of Chicago! The photos he helps you capture are perfect. Thank you!"..."
star-5
30 Minute Lake Michigan Speedboat Ride
"Love this tour, the tour guide was very nice and knowledgeable the weather was very nice as well , I highly recommend this tour"..."

Frequently Asked Questions

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