Sailing in and near Chicago, IL


Monday Night Sunset Skyline Cruise
Monday Night Sunset Skyline Cruise
200 North Breakwater Access, Chicago3.2 mi
$25.00 $7.50
70% discount_off
Monday, Aug 22, 2022 / 7:30pm
Friday Evening Happy Hour Cruise - Friday, Aug 26, 2022 / 4:30pm (Boarding Begins at 3:45pm)
Friday Evening Happy Hour Cruise - Friday, Aug 26, 2022 / 4:30pm (Boarding Begins at 3:45pm)
200 North Breakwater Access, Chicago3.2 mi
$35.00 $16.00
54% discount_off
Friday, Aug 26, 2022 / 4:30pm (Boarding Begins at 3:45pm)
Monday or Tuesday Night Sunset Cruise for 1, 2, or 4 (Up to 63% Off).
Monday or Tuesday Night Sunset Cruise for 1, 2, or 4 (Up to 63% Off).
200 North Breakwater Access, Chicago3.2 mi
4.4
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2,426 ratings
$32.00 $12.00
63% discount_off
Monday or Tuesday Night Sunset Skyline Cruise for One
Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
online_deal
$79.00
Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
90-Minute Chicago Architecture Boat Tour One, Two, Three, or Four (Up to 41% Off)
90-Minute Chicago Architecture Boat Tour One, Two, Three, or Four (Up to 41% Off)
900 South Wells Street, Chicago1.7 mi
4.7
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4,770 ratings
$49.00 $29.00
41% discount_off
90-Minute Chicago Architecture Boat Tour for One
Four- or Eight-Hour Boat Rental for Up to 12 People from The Debonair (Up to 20% Off)
Four- or Eight-Hour Boat Rental for Up to 12 People from The Debonair (Up to 20% Off)
1559 South Lake Shore Drive, Chicago2.1 mi
$6,000.00 $4,999.00
17% discount_off
Four-Hour Boat Rental for Up to 12 People
1 bought
Three-Hour Tiki Boat Cruise with Crew at Chicago Tiki Boat (Up to 57% Off). Two Options Available.
Three-Hour Tiki Boat Cruise with Crew at Chicago Tiki Boat (Up to 57% Off). Two Options Available.
Monroe Harbor, Chicago2.7 mi
4.6
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40 ratings
$1,451.97 $784.00$627.20
 Sale Ends 8/16
Three-Hour Tiki Boat Cruise with Crew; Valid Monday–Thursday, Valid to
90- or 45-Minute Architecture, or Sunset Cruise at Wendella Tours & Cruises
90- or 45-Minute Architecture, or Sunset Cruise at Wendella Tours & Cruises
400 N Michigan Avenue, Chicago3.0 mi
4.8
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2,690 ratings
$25.00
90 Minute River Architecture Tour
Historical and Architectural Boat Tour for One, Two, or Four from Chicago Fireboat Tours (Up to 53% Off).
Historical and Architectural Boat Tour for One, Two, or Four from Chicago Fireboat Tours (Up to 53% Off).
111 North Lake Shore Drive, Chicago3.1 mi
4.9
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544 ratings
$40.00 $29.00$23.20
 Sale Ends 8/16
Historical and Architectural Boat Tour for One; Valid Weekdays Only
3- or 4-Night Cabin Stay and Boat Rental for 2 from Gold Mine Camp (Up to 64% Off). 4 Options Available.
3- or 4-Night Cabin Stay and Boat Rental for 2 from Gold Mine Camp (Up to 64% Off). 4 Options Available.
7036 Gold Mine Road, Orr
3.8
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53 ratings
$750.00 $350.00$280.00
 Sale Ends 8/16
Three-Night Cabin Stay and Daily Boat Rental for Two; Valid Sunday–Thursday
Lake Michigan Fireworks Tiki Bar Cruise from Chicago Riverwalk
Lake Michigan Fireworks Tiki Bar Cruise from Chicago Riverwalk
online_deal
$50.00
Lake Michigan Fireworks Tiki Bar Cruise from Chicago Riverwalk
3-Hour Sunset Boat Tour for One Child or Adult from Pronatours - Mexico
3-Hour Sunset Boat Tour for One Child or Adult from Pronatours - Mexico
online_deal
$25.00
3-Hour Sunset Boat Tour for One Child (Ages 4–9)
3 bought
Chicago by Night! Cruise
Chicago by Night! Cruise
112 East Wacker Drive, Chicago3.0 mi
4.8
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18 ratings
$45.00 $41.28
8% discount_off
Chicago by Night! Cruise
75-Minute Architecture River Tour for One Child or Adult from Shoreline Sightseeing (Up to 12% Off)
75-Minute Architecture River Tour for One Child or Adult from Shoreline Sightseeing (Up to 12% Off)
2 Locations3.0 mi
4.9
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3,337 ratings
$49.05 $43.00
12% discount_off
75-Minute Architecture River Tour For One
Wednesday Cruise With Sunsets, Drinks, & Music
Wednesday Cruise With Sunsets, Drinks, & Music
200 North Breakwater Access, Chicago3.2 mi
$25.00 $19.25
23% discount_off
Wednesday, Sep 7, 2022 / 7:30pm
Labor Day Weekend Cocktail Cruise
Labor Day Weekend Cocktail Cruise
200 North Breakwater Access, Chicago3.2 mi
$20.00 $18.00
10% discount_off
Saturday, Sep 3, 2022 / 12:30pm (Boarding Begins at 11:45am) - General Admission
Wednesday Fireworks & Sunset Cruise or Thursday Sunset Cruise for One, Two, or Four (Up to 65% Off).
Wednesday Fireworks & Sunset Cruise or Thursday Sunset Cruise for One, Two, or Four (Up to 65% Off).
200 North Breakwater Access, Chicago3.2 mi
4.4
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2,428 ratings
$32.00 $14.00$11.20
 Sale Ends 8/16
Wednesday Night Fireworks or Thursday Night Sunset Cocktail Cruise for One
Friday Happy Hour Luau Cruise for One, Two, or Four (Up to 40% Off).
Friday Happy Hour Luau Cruise for One, Two, or Four (Up to 40% Off).
200 North Breakwater Access, Chicago3.2 mi
4.4
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2,426 ratings
$25.00 $15.00
40% discount_off
Friday Happy Hour Luau Skyline Cruise for One
Labor Day Weekend Afternoon, Sunset, Evening, & Night Cruises (September 3–5) (Up to 46% Off)
Labor Day Weekend Afternoon, Sunset, Evening, & Night Cruises (September 3–5) (Up to 46% Off)
200 North Breakwater Access, Chicago3.2 mi
$35.00 $19.00
46% discount_off
09/03/22, 12:30 p.m.–3 p.m.: Saturday Afternoon Hawaiian Luau Cruise for One
60+ bought
Up to 44% Off on Helicopter Ride at Sedona Helicopter Tours
Up to 44% Off on Helicopter Ride at Sedona Helicopter Tours
235 Air Terminal Drive, Sedona
4.7
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36 ratings
$203.00 $142.00$113.60
 Sale Ends 8/16
Sedona Helicopter Red Rock Tour for One person
$87.20 for Dolphin Encounter, Catamaran & Snorkel Tour at Aquatours ($188 Value)
$87.20 for Dolphin Encounter, Catamaran & Snorkel Tour at Aquatours ($188 Value)
Kukulcan Boulevard, Hotel Zone, Cancún, QR
4.6
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1,172 ratings
$188.00 $109.00$87.20
 Sale Ends 8/16
Dolphin Encounter, Catamaran & Snorkel Tour for One Person (Age 8+)
Premier Dinner Cruise on Lake Michigan
Premier Dinner Cruise on Lake Michigan
600 East Grand Avenue, Chicago
4.5
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98 ratings
$131.90
Premier Dinner Cruise on Lake Michigan
Chicago Signature Dinner Cruise for One from City Cruises
Chicago Signature Dinner Cruise for One from City Cruises
600 East Grand Avenue, Chicago
4.5
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97 ratings
$109.90 $65.94
40% discount_off
Chicago Signature Dinner Cruise; Multiple Days Available
Helicopter Tour - Downtown Chicago
Helicopter Tour - Downtown Chicago
online_deal
$239.00
Helicopter Tour - Downtown Chicago
Premier Dinner Cruise on The Chicago River
Premier Dinner Cruise on The Chicago River
455 North Cityfront Plaza Drive, Chicago
4.5
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98 ratings
$141.90
Premier Dinner Cruise on The Chicago River
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
30 S Columbus Dr, Chicago2.6 mi
$433.82
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
One or Two Three-Hour Semi-Private Sailing or Racing Lessons from 3rd Coast Cruising (Up to 77% Off)
One or Two Three-Hour Semi-Private Sailing or Racing Lessons from 3rd Coast Cruising (Up to 77% Off)
400 E Monroe St, Chicago2.9 mi
4.7
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56 ratings
$300.00 $89.00$71.20
 Sale Ends 8/16
One Three-Hour Semi-Private Sailing or Racing Lesson
Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 64% Off)
Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 64% Off)
111 North Lake Shore Drive, Chicago3.2 mi
4.3
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721 ratings
$660.00 $299.00$239.20
 Sale Ends 8/16
Two-Hour BYOB Sailing Cruise for Two
$512 for Six-Hour Private Sailing Lesson at Red Gear Racing ($800 Value)
$512 for Six-Hour Private Sailing Lesson at Red Gear Racing ($800 Value)
1001 Gulf Blvd, Clearwater
$800.00 $640.00$512.00
 Sale Ends 8/16
Six-Hour Private Sailing Lesson (Ages 14 and Up)
1 bought
Three- or Four-Hour Yacht Cruise at Believe Tours Chicago (Up to 36% Off). Four Options Available.
Three- or Four-Hour Yacht Cruise at Believe Tours Chicago (Up to 36% Off). Four Options Available.
3155 South Lake Shore Drive, Chicago2.4 mi
$1,500.00 $1,200.00$960.00
 Sale Ends 8/16
Three-Hour Yacht Cruise; Valid Monday–Thursday