Chicago
Cruises, Sailing & Water Tours

Chicago : Cruises, Sailing & Water Tours

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

37 reviews

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted ...  More info

  • Location: Chicago, Illinois
  • Duration: 6 hours
From USD $124.00

Chicago Architecture River Cruise

1,020 reviews

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, ...  More info

  • Location: Chicago, Illinois
  • Duration: 75 minutes
From USD $33.60
USD $39.20 Save:USD $5.60

Chicago City Tour and Chicago River Cruise

70 reviews

Discover Chicago from both land and water on this scenic half-day tour. Take a narrated coach tour through the city’s South Side and see highlights ...  More info

  • Location: Chicago, Illinois
  • Duration: 4 hours
From USD $60.00

Lake Michigan Sightseeing Cruise

23 reviews

Admire all of Chicago's fabulous lakefront sights and attractions on this 40-minute Lake Michigan boat tour. Cruise along Lake Michigan and ...  More info

  • Location: Chicago, Illinois
  • Duration: 40 minutes
From USD $19.60

Chicago Architecture Boat Tour by Night

12 reviews

See Chicago by night and learn about its rich architectural history on a 75-minute evening sightseeing cruise along the Chicago River. Explore three ...  More info

  • Location: Chicago, Illinois
  • Duration: 75 minutes
From USD $33.60

Viator VIP: Exclusive Chicago New Year's Eve Luxury Dinner Cruise

Skip the crowded bars and restaurants this December 31st, and ring in the new year instead aboard a luxurious yacht. As you glide ...  More info

  • Location: Chicago, Illinois
  • Duration: 4 hours
From USD $325.00

Chicago Sunset Dinner Cruise with Buffet

46 reviews

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 ...  More info

  • Location: Chicago, Illinois
  • Duration: 3 hours
From USD $101.49

Chicago Halloween Haunted Cruise

2 reviews

Add a new adventure to your Halloween festivities this year. Come join all the fun on a haunted one hour speedboat cruise on Lake Michigan. More info

  • Location: Chicago, Illinois
  • Duration: 60 minutes
From USD $37.06

Chicago Lunch Cruise

10 reviews

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this 2-hour ...  More info

  • Location: Chicago, Illinois
  • Duration: 2 hours
From USD $71.94

Chicago Dinner Cruise

38 reviews

Expect the exceptional on this 3-hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop ...  More info

  • Location: Chicago, Illinois
  • Duration: 3 hours
From USD $125.99

Chicago Brunch Cruise

3 reviews

Experience Chicago's amazing skyline views from a unique vantage point on board this unforgettable 2 hour brunch cruise. With unsurpassed views of the ...  More info

  • Location: Chicago, Illinois
  • Duration: 2 hours
From USD $74.66

Americas Cup Sailing Racing Experience on Lake Michigan

Sail in beautiful Lake Michigan in between The Shedd Aquarium and Navy Pier, aboard the famous America’s Cupyachts: ‘Stars and Stripes’ and ‘Abracadabra.’  ...  More info

  • Location: Chicago, Illinois
  • Duration: 3 hours
From USD $150.00