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Here are your 25 search results for Cruises, Sailing & Water Tours in Chicago, United States

Chicago Odyssey Dinner Cruise

Chicago Odyssey Dinner Cruise - Chicago, Illinois
Star Rating

Duration: 3 hours
Location: Chicago, Illinois

From USD
$108.66

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior ... More info ›

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Enjoy a 3-course plated meal with celebrity-chef inspired dishes prepared from fresh ingredients right on board. Dance the night away to DJ entertainment or simply relax in the elegant ambiance and take in the unmatched views of the world-famous Chicago skyline as you sail along the shores of Lake Michigan.

Step Aboard...  

You cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Guests who are 21 years of age or older will receive a complimentary glass of champagne to sip on upon boarding

Indulge your senses... 
A celebrity-chef inspired menu of seasonal hors d'oeuvres, entrées, accompaniments and desserts is freshly prepared onboard daily, Complement your sumptuous meal with a drink from the full service bar featuring an expanded microbrewery selection, creative cocktails and a refreshed wine list. DJ entertainment will set the mood for an unforgettable evening on the water. Dance to everything from classic jazz to contemporary favorites.

Take home a memory... 
Return, hours later. Relaxed. Refreshed. As you depart, you'll find your boarding photo ready for purchase. 

Sample Menu

First Course
  • Caesar Salad
  • Lobster Soup
Entrees
  • Jumbo Lump Crab Cakes
  • Oven Baked Atlantic Salmon Filet
  • Maple & Mustard Glazed Chicken Breast
  • Braised Beef Short Ribs
  • Jumbo Forest Mushroom Ravioli
Desserts
  • Eli's Original Cheesecake
  • Duo of Sorbet
  • Freshly Cut Fruit and Fresh Strawberries
  • Chocolate Decadent Cake
  • Odyssey Signature Warm Butter Cake

Chicago Fireworks Dinner Cruise
In the summer months, upgrade your Chicago Dinner Cruise experience to include a spectacular fireworks display on Wednesdays, Saturdays and select Thursday's and Fridays. You will observe the show from the decks of the ship and see the magnificent sky lit up at night.


Less info

Spirit of Chicago Sunset Dinner Cruise with Buffet

Spirit of Chicago Sunset Dinner Cruise with Buffet - Chicago, Illinois
Star Rating

Duration: 3 hours
Location: Chicago, Illinois

From USD
$108.66

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.

This Chicago sunset dinner cruise is a fun and unique way to see some of the Windy City’s famous landmarks ... More info ›

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.

This Chicago sunset dinner cruise is a fun and unique way to see some of the Windy City’s famous landmarks. Enjoy drinks on the deck of a sleek, sophisticated cruiser, as the downtown Chicago skyline lights up when the sun sets.

You’ll be treated to a sumptuous all-you-can-eat buffet, complete with a carving station. As you enjoy your meal in the elegant setting of the ship’s dining room, you’ll be entertained by the colorful characters of the ship’s cabaret. After dinner, the dance floor heats up as a top Chicago DJ spins your favorite songs.

You’ll be enchanted by the nighttime backdrop of the illuminated Chicago skyline - be sure to bring your camera! This 3-hour Chicago dinner cruise is an excellent prelude to a night on the town.

Chicago Fireworks Dinner Cruise
In the summer months, upgrade your Chicago Dinner Cruise experience to include a spectacular fireworks display on Wednesdays and Saturdays. You will observe the show from the decks of the ship and see the magnificent sky lit up at night.

Less info

Lake Michigan and Chicago River Architecture Cruise by Speedboat

Lake Michigan and Chicago River Architecture Cruise by Speedboat - Chicago, Illinois
Star Rating

Duration: 75 minutes
Location: Chicago, Illinois

From USD
$42.50

The rumors are true! The best way to soak in all of Chicago's rich architectural beauty is by joining us on our 75-minute River and Lake Architectural Cruise. Enjoy a relaxing ride along the Chicago River and learn all about the history of this beautiful city and its landmarks ... More info ›

The rumors are true! The best way to soak in all of Chicago's rich architectural beauty is by joining us on our 75-minute River and Lake Architectural Cruise. Enjoy a relaxing ride along the Chicago River and learn all about the history of this beautiful city and its landmarks. And don't forget the tour's grand finale, a thrilling speedboat ride on Lake Michigan!

Meet your guide at Navy Pier, where you'll board your boat. As you take off along the water, see and hear about the dozens of skyscrapers lining the Chicago River, including the Sears Tower and the Tribune Tower. Learn when and why the flow of the Chicago River was reversed, how Chicago architects pioneered skyscraper construction and a variety of other tales and tidbits of Chicago's history from your guide.

Then, take a thrilling speedboat ride along the lake for spectacular views of the Chicago skyline from Lake Michigan. From the water, you'll see Buckingham Fountain, Grant Park, beautiful Chicago Harbor and Chicago's Museum Campus.

Your tour will conclude with drop-off at your original departure point.

Less info

Chicago Odyssey Lunch Cruise

Chicago Odyssey Lunch Cruise - Chicago, Illinois
Star Rating

Duration: 2 hours
Location: Chicago, Illinois

From USD
$77.38

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Satisfy your appetite and take in breathtaking views of Chicago's skyline on this 2-hour lunch cruise. While you are on board, not only can you enjoy a freshly prepared three-course meal, but also enjoy live musical entertainment which makes for a truly unforgettable experience.

Step Aboard...  

You cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Relax with a beverage or tour the ship's three climate-controlled decks ... More info ›

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Satisfy your appetite and take in breathtaking views of Chicago's skyline on this 2-hour lunch cruise. While you are on board, not only can you enjoy a freshly prepared three-course meal, but also enjoy live musical entertainment which makes for a truly unforgettable experience.

Step Aboard...  

You cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Relax with a beverage or tour the ship's three climate-controlled decks. Watching the boat cast-off from one of the observation decks is a great way to start your afternoon cruise. Enjoy your three course meal and also live entertainment on board from start to finish!

Indulge your senses...  
A celebrity-chef inspired menu of seasonal hors d'oeuvres, entrées, accompaniments and desserts is freshly prepared onboard daily, Complement your sumptuous meal with a drink from the full service bar featuring an expanded microbrewery selection, creative cocktails and a refreshed wine list.

Sample Menu
First Course
  • Caesar Salad
  • Lobster Soup
Entrées:
  • Oven Baked Atlantic Salmon Filet
  • Maple & Mustard Glazed Chicken Breast
  • Braised Beef Short Rib
  • Jumbo Forest Mushroom Ravioli
Desserts:
  • Duo of Sorbet
  • Freshly Cut Fruit & Fresh Strawberries
  • Chocolate Decadent Cake
  • Odyssey Signature Warm Butter Cake

Less info

Booking.com

Chicago Architecture River Cruise

Chicago Architecture River Cruise - Chicago, Illinois
Star Rating

Duration: 75 minutes
Location: Chicago, Illinois

Special Offer
From USD
$41.44

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building ... More info ›

Special Offer - Book and save 9% compared to the local supplier's prices!  Offer valid Mon-Thu only. - Book Now!

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

Take an architecture cruise down the Chicago River and learn about the city’s famed architecture from your knowledgeable guide. Board your tour at Navy Pier for an exciting journey that takes you down all three branches of the historic Chicago River and past impressive architectural landmarks.

Pass by more than 40 distinctive buildings on your cruise including the John Hancock Center, the Wrigley Building, the Aon Center, Willis Tower (Sears Tower), the IBM Building and more. Your guide, an expert in architecture, will recount the two major events that helped shape the architectural history of the city. Learn about how the invention of balloon-frame construction revolutionized how homes were built, and hear the dramatic story of Chicago's rise from the Great Fire of 1871. Both of these milestones led Chicago to become one of the cradles of modern American architecture.

Along the scenic 75-minute route, see buildings by world-famous architects including Mies van der Rohe, Helmut Jahn and Skidmore, Owings and Merrill (SOM). This river tour provides the best advantage point to admire the distinct city skyline and marvel at world-famous architecture while learning about Chicago's fascinating history.

For a full list of Chicago architectural wonders seen on this tour, see the Itinerary section below.

Special Offer - Book and save 9% compared to the local supplier's prices!  Offer valid Mon-Thu only. - Book Now!

Less info

Chicago Odyssey Brunch Cruise

Chicago Odyssey Brunch Cruise - Chicago, Illinois
Star Rating

Duration: 2 hours
Location: Chicago, Illinois

From USD
$99.14

There is no better way to see Chicago than from the waters of Lake Michigan. Enjoy the amazing skyline views on board during this unforgettable 2-hour brunch cruise on the Odyssey Chicago. With unsurpassed views of the Sears Tower, the John Hancock Tower, to the Museum campus and the Aon Center, you'll be stunned by the beauty this city has to offer!

Step Aboard...
You cruise experience begins as you board the luxury yacht at Navy Pier ... More info ›

There is no better way to see Chicago than from the waters of Lake Michigan. Enjoy the amazing skyline views on board during this unforgettable 2-hour brunch cruise on the Odyssey Chicago. With unsurpassed views of the Sears Tower, the John Hancock Tower, to the Museum campus and the Aon Center, you'll be stunned by the beauty this city has to offer!

Step Aboard...
You cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Guests who are 21 years of age or older will receive a complimentary mimosa to sip. A great way to start your afternoon is by watching the boat castoff from one of the observation decks.

Indulge your senses...
Bring your appetite when you return to your private table, the Executive Chef and galley staff present you with an imaginative buffet of appetizers, entrees, salads and desserts that is sure to please any number of tastes.

Throughout the cruise our DJ entertainment provides the music...
Dance or relax while the DJ entertains you with a beautiful mix of everything from soft classics to today's favorites.

Take home a memory...
Return, hours later. Relaxed. Refreshed. As you depart, you'll find your boarding photo ready for purchase.

Sample Menu

Breakfast selections:

  • Seasonal Fruit
  • Breakfast Pastries
  • Smoked Salmon
  • Scrambled Eggs
  • Breakfast meats
  • Breakfast Potatoes 
  • Build-your-own Belgian Waffle Station
Lunch Options
  • Caesar Salad
  • Shrimp and Farfalle Pasta Salad
  • Potato Salad
  • Roasted Baby Carrots
  • Roasted Cedar Plank Oregano Salmon
  • Maple & Mustard Glazed Chicken
  • Hand-Carved Striploin, USDA Choice

Desserts
  • Odyssey Signature Dessert Station
  • Chocolate Fondue

Less info