Sailing in Cicero, IL


image for $149 for Soaring Flight Orientation and 3,000 Foot Sail Plane Ride at Sky Soaring Glider Club ($299 Value)
$149 for Soaring Flight Orientation and 3,000 Foot Sail Plane Ride at Sky Soaring Glider Club ($299 Value)

2-seat glider soars 3,000 ft above Hampshire countryside while commercial pilot mans controls

Hampshire, IL • 44.8 mi
10+ bought
$299 $149
View Deal
image for $149 for Soaring Flight Orientation and 3,000 Foot Sail Plane Ride at Sky Soaring Glider Club ($299 Value)
$149 for Soaring Flight Orientation and 3,000 Foot Sail Plane Ride at Sky Soaring Glider Club ($299 Value)
Hampshire, IL • 44.8 mi
10+ bought
$299 $149
image for Two-Hour Private Cruise for Up to 6 from New Buffalo <strong>Sailing</strong> Excursions (Up to 45% Off).
TRENDING
Two-Hour Private Cruise for Up to 6 from New Buffalo Sailing Excursions (Up to 45% Off).

Here are some things to know about the sailing excursions.

New Buffalo
10+ bought
$300 $169
View Deal
image for Two-Hour Private Cruise for Up to 6 from New Buffalo <strong>Sailing</strong> Excursions (Up to 45% Off).
TRENDING
Two-Hour Private Cruise for Up to 6 from New Buffalo Sailing Excursions (Up to 45% Off).
New Buffalo
10+ bought
$300 $169
image for $449 for the "Fundamentals of <strong>Sailing</strong>" Course from Celestial Sails ($1,000 Value)
$449 for the "Fundamentals of Sailing" Course from Celestial Sails ($1,000 Value)

Professional sailors offer an introductory course to sailing that takes place on 44-foot yacht.

31st Street Harbor • 7.6 mi
3 bought
$1,000 $449
View Deal
image for $449 for the "Fundamentals of <strong>Sailing</strong>" Course from Celestial Sails ($1,000 Value)
$449 for the "Fundamentals of Sailing" Course from Celestial Sails ($1,000 Value)
31st Street Harbor • 7.6 mi
3 bought
$1,000 $449
image for One or Two Three-Hour Introductory <strong>Sailing</strong> or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)
One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)

$99 for one three-hour introductory sailing or racing lesson ($300 value).

DuSable Harbor • 7.7 mi
70+ bought
$300 $99
View Deal
image for One or Two Three-Hour Introductory <strong>Sailing</strong> or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)
One or Two Three-Hour Introductory Sailing or Racing Lessons from 3rd Coast Cruising (Up to 68% Off)
DuSable Harbor • 7.7 mi
70+ bought
$300 $99
image for Private Lakefront <strong>Sailing</strong> Tours with Windy City <strong>Sailing</strong> (Up to 30% Off)
Private Lakefront Sailing Tours with Windy City Sailing (Up to 30% Off) at Windy City Sailing

Private Lakefront Sailing Tour: Saturday - Sunday.

North Side • 9.4 mi
3 bought
$600 $425
View Deal
image for Private Lakefront <strong>Sailing</strong> Tours with Windy City <strong>Sailing</strong> (Up to 30% Off)
Private Lakefront Sailing Tours with Windy City Sailing (Up to 30% Off) at Windy City Sailing
North Side • 9.4 mi
3 bought
$600 $425
image for One, Three, or Five Three-Hour <strong>Sailing</strong> Lessons at Sailboat-X.
One, Three, or Five Three-Hour Sailing Lessons at Sailboat-X.

US Sailing–certified instructors teach students to rig the boat and take the helm on a 33-foot vessel.

Chicago • 7.8 mi
9 bought
$125 $66
View Deal
image for One, Three, or Five Three-Hour <strong>Sailing</strong> Lessons at Sailboat-X.
One, Three, or Five Three-Hour Sailing Lessons at Sailboat-X.
Chicago • 7.8 mi
9 bought
$125 $66
image for Navy Pier <strong>Sailing</strong> Cruises at Celestial Sails (Up to 57% Off)
Navy Pier Sailing Cruises at Celestial Sails (Up to 57% Off)

Three-Hour Sailing Charter (Six People).

31st Street Harbor • 7.6 mi
3 bought
$437 $189
View Deal
image for Navy Pier <strong>Sailing</strong> Cruises at Celestial Sails (Up to 57% Off)
Navy Pier Sailing Cruises at Celestial Sails (Up to 57% Off)
31st Street Harbor • 7.6 mi
3 bought
$437 $189
image for Monday Night Sunset Cocktail Cruise
Monday Night Sunset Cocktail Cruise at Anita Dee II Yacht
Chicago • 7.8 mi
$25 $16.50
View Deal
image for Monday Night Sunset Cocktail Cruise
Monday Night Sunset Cocktail Cruise at Anita Dee II Yacht
Chicago • 7.8 mi
$25 $16.50
image for Two or Three-Hour Pontoon Boat Rental for eight or 12 with Chicago Boat Rentals (Up to 56% Off)
TRENDING
Two or Three-Hour Pontoon Boat Rental for eight or 12 with Chicago Boat Rentals (Up to 56% Off)

Boat rental service specializes in providing pontoons for eight or 12 that can be driven by guests with a few minutes’ training

Goose Island • 6.4 mi
210+ bought
$300 $139
View Deal
image for Two or Three-Hour Pontoon Boat Rental for eight or 12 with Chicago Boat Rentals (Up to 56% Off)
TRENDING
Two or Three-Hour Pontoon Boat Rental for eight or 12 with Chicago Boat Rentals (Up to 56% Off)
Goose Island • 6.4 mi
210+ bought
$300 $139
image for Two-Hour Electric or Pontoon Boat Rental for up to Twelve People at Vantage Boat Share (Up to 50% Off)
TRENDING
Two-Hour Electric or Pontoon Boat Rental for up to Twelve People at Vantage Boat Share (Up to 50% Off)

Boaters discover the beauty of Chicago’s local waterways surrounding the city during their boating experience

Chicago • 6.7 mi
60+ bought
$200 $99
View Deal
image for Two-Hour Electric or Pontoon Boat Rental for up to Twelve People at Vantage Boat Share (Up to 50% Off)
TRENDING
Two-Hour Electric or Pontoon Boat Rental for up to Twelve People at Vantage Boat Share (Up to 50% Off)
Chicago • 6.7 mi
60+ bought
$200 $99
image for Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)

Explore the Vermilion River, the lake, and the wilderness of Northern Minnesota

Gold Mine Camp
50+ bought
$630 $229
View Deal
image for Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
Gold Mine Camp
50+ bought
$630 $229
image for Three-Hour TikiBoat Cruise with a Crew at Chicago TikiBoat (Up to 60% Off)
Three-Hour TikiBoat Cruise with a Crew at Chicago TikiBoat (Up to 60% Off)

Groups of up to 12 and a licensed captain hit the lake on a boat with a water slide, grill for barbecuing, and float rafts for lounging

Monroe Harbor • 7.5 mi
20+ bought
$780 $315
View Deal
image for Three-Hour TikiBoat Cruise with a Crew at Chicago TikiBoat (Up to 60% Off)
Three-Hour TikiBoat Cruise with a Crew at Chicago TikiBoat (Up to 60% Off)
Monroe Harbor • 7.5 mi
20+ bought
$780 $315
image for 3-Hour Party-Boat Rental with Optional Fireworks for Up to 10 People from Island Party Boat (Up to 58% Off)
3-Hour Party-Boat Rental with Optional Fireworks for Up to 10 People from Island Party Boat (Up to 58% Off)

Clients and their families or friends can experience an enjoyable day or night out on the water, topped by an optional fireworks show.

Downtown • 7.7 mi
10+ bought
$616 $259
View Deal
image for 3-Hour Party-Boat Rental with Optional Fireworks for Up to 10 People from Island Party Boat (Up to 58% Off)
3-Hour Party-Boat Rental with Optional Fireworks for Up to 10 People from Island Party Boat (Up to 58% Off)
Downtown • 7.7 mi
10+ bought
$616 $259
image for Two- or Three-Hour Boat Rental for Up to Six People from Chicago Adventure, Inc (Up to 45% Off)
Two- or Three-Hour Boat Rental for Up to Six People from Chicago Adventure, Inc (Up to 45% Off)

Groups of up to six cruise the waters of Lake Michigan in a sleek Carver 350 Mariner yacht during two- or three-hour rentals

Burnham Harbors • 7.7 mi
$740 $499
View Deal
image for Two- or Three-Hour Boat Rental for Up to Six People from Chicago Adventure, Inc (Up to 45% Off)
Two- or Three-Hour Boat Rental for Up to Six People from Chicago Adventure, Inc (Up to 45% Off)
Burnham Harbors • 7.7 mi
$740 $499
image for One Booze Cruise Ticket at Yacht Party Chicago (Up to 42% Off)
One Booze Cruise Ticket at Yacht Party Chicago (Up to 42% Off)

For up to three hours aboard a luxury yacht, guests dance as a DJ plays music; at some special events, fireworks explode overhead

Boarding at DuSable Harbor • 7.8 mi
90+ bought
$50 $29
View Deal
image for One Booze Cruise Ticket at Yacht Party Chicago (Up to 42% Off)
One Booze Cruise Ticket at Yacht Party Chicago (Up to 42% Off)
Boarding at DuSable Harbor • 7.8 mi
90+ bought
$50 $29
image for Pontoon or Runabout Rentals at SkipperBud's (Up to 51% Off)
Pontoon or Runabout Rentals at SkipperBud's (Up to 51% Off)

Renters check in and experience an exciting, memory-filled day on the water with friends and family

Multiple Locations • 46.2 mi
4 bought
$395 $195
View Deal
image for Pontoon or Runabout Rentals at SkipperBud's (Up to 51% Off)
Pontoon or Runabout Rentals at SkipperBud's (Up to 51% Off)
Multiple Locations • 46.2 mi
4 bought
$395 $195
image for $270 for a Two-Day Advanced Adventure Scuba Course with Five Dives from Dive Right In Scuba ($499 Value)
$270 for a Two-Day Advanced Adventure Scuba Course with Five Dives from Dive Right In Scuba ($499 Value)

Certified instructors who train police and fire department dive teams teach advanced scuba techniques during dives at a local quarry

Plainfield • 28.6 mi
3 bought
$499 $270
View Deal
image for $270 for a Two-Day Advanced Adventure Scuba Course with Five Dives from Dive Right In Scuba ($499 Value)
$270 for a Two-Day Advanced Adventure Scuba Course with Five Dives from Dive Right In Scuba ($499 Value)
Plainfield • 28.6 mi
3 bought
$499 $270
image for Lake Michigan and Chicago River Architecture Cruise by Speedboat
NEW
Lake Michigan and Chicago River Architecture Cruise by Speedboat at Entertainment Cruises
Chicago
$42.87
View Deal
image for Lake Michigan and Chicago River Architecture Cruise by Speedboat
NEW
Lake Michigan and Chicago River Architecture Cruise by Speedboat at Entertainment Cruises
Chicago
$42.87
image for Semi-Private 3-Hour Sunset Cruise for Up to 4 or 6 People from 3rd Coast Cruising (Up to 56% Off)
Semi-Private 3-Hour Sunset Cruise for Up to 4 or 6 People from 3rd Coast Cruising (Up to 56% Off)

For three hours, you can cruise along Lake Michigan with a group of up to 5 friends as the sun sets in the distance

DuSable Harbor • 7.7 mi
$900 $500
View Deal
image for Semi-Private 3-Hour Sunset Cruise for Up to 4 or 6 People from 3rd Coast Cruising (Up to 56% Off)
Semi-Private 3-Hour Sunset Cruise for Up to 4 or 6 People from 3rd Coast Cruising (Up to 56% Off)
DuSable Harbor • 7.7 mi
$900 $500
image for BYOB Three-Hour Scenic <strong>Sailing</strong> Cruise for One, Two, Four, or Six at Sailboat-X (Up to 54% Off)
BYOB Three-Hour Scenic Sailing Cruise for One, Two, Four, or Six at Sailboat-X (Up to 54% Off)

Three-Hour Scenic Sailing Cruise for Two People.

Chicago • 7.8 mi
8 bought
$125 $66
View Deal
image for BYOB Three-Hour Scenic <strong>Sailing</strong> Cruise for One, Two, Four, or Six at Sailboat-X (Up to 54% Off)
BYOB Three-Hour Scenic Sailing Cruise for One, Two, Four, or Six at Sailboat-X (Up to 54% Off)
Chicago • 7.8 mi
8 bought
$125 $66
image for Private Fireworks Cruise
Private Fireworks Cruise at Come Sailing, Inc.

Groupon is not affiliated with or sponsored by the Come Sailing, Inc.

Chicago
$389.76
View Deal
image for Private Fireworks Cruise
Private Fireworks Cruise at Come Sailing, Inc.
Chicago
$389.76
image for Private Day <strong>Sailing</strong> on Lake Michigan
Private Day Sailing on Lake Michigan at Come Sailing, Inc.

Furthermore, by boarding any of our sailboats you are granting Come Sailing, Inc.

Chicago
$389.76
View Deal
image for Private Day <strong>Sailing</strong> on Lake Michigan
Private Day Sailing on Lake Michigan at Come Sailing, Inc.
Chicago
$389.76
image for Private Morning Sail on Lake Michigan
Private Morning Sail on Lake Michigan at Come Sailing, Inc.

... shareholders, and representatives the right and permission to use such film, photographs and recordings and to use your name, voice, image, and likeness for the purpose of promoting Come Sailing, Inc.

Chicago
$389.76
View Deal
image for Private Morning Sail on Lake Michigan
Private Morning Sail on Lake Michigan at Come Sailing, Inc.
Chicago
$389.76
image for Lake Michigan Speedboat Ride
Lake Michigan Speedboat Ride at Entertainment Cruises
Chicago
$27.79
View Deal
image for Lake Michigan Speedboat Ride
Lake Michigan Speedboat Ride at Entertainment Cruises
Chicago
$27.79
image for Music at Joe's Live - Rosemont
TOP SELLER
Music at Joe's Live - Rosemont
Far North Side • 10.9 mi
$8 $3.50
View Deal
image for Music at Joe's Live - Rosemont
TOP SELLER
Music at Joe's Live - Rosemont
Far North Side • 10.9 mi
$8 $3.50
image for All-Inclusive Rooftop View of Florida Georgia Line, Backstreet Boys, and Nelly at Wrigley Field on Saturday, August 12
All-Inclusive Rooftop View of Florida Georgia Line, Backstreet Boys, and Nelly at Wrigley Field on Saturday, August 12

Enjoy rooftop views while singing along to hits such as “This Is How We Roll,” “I Want It That Way,” and “Hot in Herre”

Skybox on Sheffield • 8.8 mi
90+ bought
$222.39 $159
View Deal
image for All-Inclusive Rooftop View of Florida Georgia Line, Backstreet Boys, and Nelly at Wrigley Field on Saturday, August 12
All-Inclusive Rooftop View of Florida Georgia Line, Backstreet Boys, and Nelly at Wrigley Field on Saturday, August 12
Skybox on Sheffield • 8.8 mi
90+ bought
$222.39 $159
image for Jimmy Buffett and Huey Lewis All-Inclusive Rooftop Experience on Saturday, July 15 at 7 p.m.
Jimmy Buffett and Huey Lewis All-Inclusive Rooftop Experience on Saturday, July 15 at 7 p.m.

Legendary singer-songwriter behind “Margaritaville” joins forces with iconic pop-rocker of “The Power of Love” fame

Skybox on Sheffield Rooftop • 8.8 mi
40+ bought
$195.51 $99
View Deal
image for Jimmy Buffett and Huey Lewis All-Inclusive Rooftop Experience on Saturday, July 15 at 7 p.m.
Jimmy Buffett and Huey Lewis All-Inclusive Rooftop Experience on Saturday, July 15 at 7 p.m.
Skybox on Sheffield Rooftop • 8.8 mi
40+ bought
$195.51 $99
image for All-Inclusive Florida Georgia Line, Backstreet Boys, and Nelly Concert Rooftop Ticket on Saturday, August 12
All-Inclusive Florida Georgia Line, Backstreet Boys, and Nelly Concert Rooftop Ticket on Saturday, August 12

Country-pop duo deliver chart-topping hits like “Cruise” and “This Is How We Roll;” Backstreet Boys and Nelly join

Lakeview Baseball Club • 8.8 mi
70+ bought
$222.39 $169
View Deal
image for All-Inclusive Florida Georgia Line, Backstreet Boys, and Nelly Concert Rooftop Ticket on Saturday, August 12
All-Inclusive Florida Georgia Line, Backstreet Boys, and Nelly Concert Rooftop Ticket on Saturday, August 12
Lakeview Baseball Club • 8.8 mi
70+ bought
$222.39 $169
image for 60-Minute Introductory Flight at Elite Flight Training and Aircraft Management ( 41% Off)
60-Minute Introductory Flight at Elite Flight Training and Aircraft Management ( 41% Off)

Professional and qualified instructors will provide you with help to take your first steps in the air

Kankakee
5 bought
$179 $105
View Deal
image for 60-Minute Introductory Flight at Elite Flight Training and Aircraft Management ( 41% Off)
60-Minute Introductory Flight at Elite Flight Training and Aircraft Management ( 41% Off)
Kankakee
5 bought
$179 $105
image for 3- or 5-Hour Party Bus Rental for 25 Passengers from Party Bus Hoppers (Up to 67% Off)
3- or 5-Hour Party Bus Rental for 25 Passengers from Party Bus Hoppers (Up to 67% Off)

Passengers cruise in high style to events on a party bus that can seat up to 25 passengers

Chicago
$1,100 $399
View Deal
image for 3- or 5-Hour Party Bus Rental for 25 Passengers from Party Bus Hoppers (Up to 67% Off)
3- or 5-Hour Party Bus Rental for 25 Passengers from Party Bus Hoppers (Up to 67% Off)
Chicago
$1,100 $399
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