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Here are your search results for all 6 Cruises, Sailing & Water Tours in Chicago, United States

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Chicago Dinner Cruise

Chicago Dinner Cruise - Chicago, Illinois Star Rating

Duration: 3 hours
Location: Chicago, Illinois

From USD
$112.74

Step aboard the Chicago Dinner Cruise and enjoy a three-hour escape on Lake Michigan. Relaxing in the elegant ambiance that only a true luxury cruising vessel can provide, you'll sail along the lake shore and have unmatched views of the world-famous Chicago skyline

For an experience that begins well before the cruise departs, arrive early dressed in your most festive attire. Enjoy the electric atmosphere of Navy Pier, alive with wandering entertainers and remarkable views that offer a taste of the experience to come.

The Captain and crew will greet you as you step aboard, and the ship's photographer will record the moment for your party. Once on deck, your host will greet you and escort you to your private table, where your wait staff will introduce themselves and give you the opportunity to decide how you'd like them to pace your service. From the three climate-controlled dining decks to the Observation deck, the dinner cruise offers a unique setting with understated Art Deco accents, reminiscent of the classic ocean liners. Be sure to visit the Captain's bridge, open to all passengers throughout most of the cruise.

A menu of creative seasonal hors d'oeuvres, appetizers, entrees and desserts is freshly prepared onboard daily, perfectly complemented by an excellent wine list. With soft piano music, spacious dance floors on each deck and live music provided by a five-piece band, the entertainment doesn't end until well after the ship returns to the pier. Dance to everything from classic jazz to contemporary favorites.


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. ... More info ›

Step aboard the Chicago Dinner Cruise and enjoy a three-hour escape on Lake Michigan. Relaxing in the elegant ambiance that only a true luxury cruising vessel can provide, you'll sail along the lake shore and have unmatched views of the world-famous Chicago skyline

For an experience that begins well before the cruise departs, arrive early dressed in your most festive attire. Enjoy the electric atmosphere of Navy Pier, alive with wandering entertainers and remarkable views that offer a taste of the experience to come.

The Captain and crew will greet you as you step aboard, and the ship's photographer will record the moment for your party. Once on deck, your host will greet you and escort you to your private table, where your wait staff will introduce themselves and give you the opportunity to decide how you'd like them to pace your service. From the three climate-controlled dining decks to the Observation deck, the dinner cruise offers a unique setting with understated Art Deco accents, reminiscent of the classic ocean liners. Be sure to visit the Captain's bridge, open to all passengers throughout most of the cruise.

A menu of creative seasonal hors d'oeuvres, appetizers, entrees and desserts is freshly prepared onboard daily, perfectly complemented by an excellent wine list. With soft piano music, spacious dance floors on each deck and live music provided by a five-piece band, the entertainment doesn't end until well after the ship returns to the pier. Dance to everything from classic jazz to contemporary favorites.


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

Chicago River and Lake Architecture Tour

Chicago River and Lake Architecture Tour - Chicago, Illinois Star Rating

Duration: 75 minutes
Location: Chicago, Illinois

From USD
$36.10

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all about Chicago's history and landmarks before the tour's grand finale, a thrilling speedboat ride on Lake Michigan.

From the boat, you'll see and hear about the dozens of skyscrapers lining the Chicago River, including the Sears Tower and the Tribune Tower.

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

Your best choice for experiencing Chicago, this tour combines coach and boat travel. It's the only tour that takes you from the lakefront, through the locks and along the river.

Along the way, you'll:

  • Learn when and why the flow of the Chicago River was reversed
  • Learn how Chicago architects pioneered skyscraper construction
  • Learn why the beautiful Chicago lakefront is almost all parkland
  • Learn about an $80 million dollar skyscraper construction mistake
  • Travel through the historic Chicago River Locks and up the Chicago River to Sears Tower
... More info ›

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all about Chicago's history and landmarks before the tour's grand finale, a thrilling speedboat ride on Lake Michigan.

From the boat, you'll see and hear about the dozens of skyscrapers lining the Chicago River, including the Sears Tower and the Tribune Tower.

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

Your best choice for experiencing Chicago, this tour combines coach and boat travel. It's the only tour that takes you from the lakefront, through the locks and along the river.

Along the way, you'll:

  • Learn when and why the flow of the Chicago River was reversed
  • Learn how Chicago architects pioneered skyscraper construction
  • Learn why the beautiful Chicago lakefront is almost all parkland
  • Learn about an $80 million dollar skyscraper construction mistake
  • Travel through the historic Chicago River Locks and up the Chicago River to Sears Tower

Less info

Chicago Sunset Dinner Cruise with Buffet

Chicago Sunset Dinner Cruise with Buffet - Chicago, Illinois

Duration: 3 hours
Location: Chicago, Illinois

From USD
$92.34

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 while being entertained by a singing ship staff 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 three-hour Chicago dinner cruise is an excellent prelude to a night on the town. ... 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 while being entertained by a singing ship staff 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 three-hour Chicago dinner cruise is an excellent prelude to a night on the town.

Less info

Chicago Lunch Cruise

Chicago Lunch Cruise - Chicago, Illinois Star Rating

Duration: 2 hours
Location: Chicago, Illinois

From USD
$63.78

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this two-hour lunch cruise. While you cruise, and enjoy a freshly prepared three-course meal, you'll enjoy magnificent views of the Windy City skyline and hear your favorite music from a live trio.

Your cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, you host 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.

When you are ready to begin lunch, order your meal from the extensive menu of creative appetizers, entrees and desserts. Bring an appetite as the food is delicious, plentiful and prepared freshly to your specifications.

Throughout the cruise the live trio sets the mood...Enjoy a wide range of music, from classic jazz to contemporary favorites.

Return to the pier relaxed and refreshed. As you depart, you'll find your boarding photo ready for purchase. ... More info ›

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this two-hour lunch cruise. While you cruise, and enjoy a freshly prepared three-course meal, you'll enjoy magnificent views of the Windy City skyline and hear your favorite music from a live trio.

Your cruise experience begins as you board the luxury yacht at Navy Pier. After a quick stop for a commemorative boarding photo, you host 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.

When you are ready to begin lunch, order your meal from the extensive menu of creative appetizers, entrees and desserts. Bring an appetite as the food is delicious, plentiful and prepared freshly to your specifications.

Throughout the cruise the live trio sets the mood...Enjoy a wide range of music, from classic jazz to contemporary favorites.

Return to the pier relaxed and refreshed. As you depart, you'll find your boarding photo ready for purchase.

Less info

Chicago Brunch Cruise

Chicago Brunch Cruise - Chicago, Illinois Star Rating

Duration: 2 hours
Location: Chicago, Illinois

From USD
$80.10

Experience Chicago's amazing skyline views from a unique vantage point on board this unforgettable 2 hour brunch cruise. With unsurpassed views of the Sears Tower, the John Hancock Tower, to the Museum campus and the Aon Center, you'll be seduced by the luxury and spaciousness of the three climate-controlled dining and observation decks while sailing on the world-famous harbor.

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.

Explore and Enjoy...
Enjoy a complimentary glass of champagne or tour the ship's three climate controlled decks. 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 live jazz trio sets the mood...
Enjoy a wide range of jazz from artists such as John Coltrane, Miles Davis and Branford Marsalis.

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

Experience Chicago's amazing skyline views from a unique vantage point on board this unforgettable 2 hour brunch cruise. With unsurpassed views of the Sears Tower, the John Hancock Tower, to the Museum campus and the Aon Center, you'll be seduced by the luxury and spaciousness of the three climate-controlled dining and observation decks while sailing on the world-famous harbor.

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.

Explore and Enjoy...
Enjoy a complimentary glass of champagne or tour the ship's three climate controlled decks. 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 live jazz trio sets the mood...
Enjoy a wide range of jazz from artists such as John Coltrane, Miles Davis and Branford Marsalis.

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

Less info

Chicago Land and Lake Half-Day Tour

Chicago Land and Lake Half-Day Tour - Chicago, Illinois Star Rating

Duration: 4 hours
Location: Chicago, Illinois

From USD
$49.99

See Chicago from the land and the water on this scenic half-day tour. This comprehensive tour shows you the South Shore business district, the Loop and the exclusive shopping areas and neighborhoods. Then, you will see Chicago from the water as you cruise past the shoreline in a beautiful streamliner yacht!

From the lake you'll see lakefront views of the Chicago River, the city's bridges and the famous Chicago Locks. There's also Navy Pier, the Coast Guard Station and other points of interest lining the shores of the longest lake in the world, Lake Michigan.

The tour ends at the boat dock at McClurg Court & Illinois Street adjacent to Michigan Avenue and its exclusive stores.

South Side sights:

  • Grant Park
  • Soldier Field
  • Adler Planetarium
  • Joseph Petrillo outdoor band-shell
  • Art Institute of Chicago
  • Orchestra Hall
  • Shedd Aquarium
  • Field Museum of Natural History
  • South Commons
  • Jackson Park
  • University of Chicago
  • Museum of Science and Industry
  • Lake Point Towers
  • Navy Pier
... More info ›

See Chicago from the land and the water on this scenic half-day tour. This comprehensive tour shows you the South Shore business district, the Loop and the exclusive shopping areas and neighborhoods. Then, you will see Chicago from the water as you cruise past the shoreline in a beautiful streamliner yacht!

From the lake you'll see lakefront views of the Chicago River, the city's bridges and the famous Chicago Locks. There's also Navy Pier, the Coast Guard Station and other points of interest lining the shores of the longest lake in the world, Lake Michigan.

The tour ends at the boat dock at McClurg Court & Illinois Street adjacent to Michigan Avenue and its exclusive stores.

South Side sights:

  • Grant Park
  • Soldier Field
  • Adler Planetarium
  • Joseph Petrillo outdoor band-shell
  • Art Institute of Chicago
  • Orchestra Hall
  • Shedd Aquarium
  • Field Museum of Natural History
  • South Commons
  • Jackson Park
  • University of Chicago
  • Museum of Science and Industry
  • Lake Point Towers
  • Navy Pier

Less info