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Sailing in Chicago, IL


BYOB <strong>Sailing</strong> Cruise with Optional Fireworks for Two or Six at Offshore Adventures (Up to 72% Off)
BYOB Sailing Cruise with Optional Fireworks for Two or Six at Offshore Adventures (Up to 72% Off)

Cruises delight with views of Chicago skyline or Navy Pier fireworks; passengers can bring along their own drinks and playlists

The Loop 3.2 mi
$220 $64
(567)
71% discount_off
Semi-Private or Private Luxury First-Class <strong>Sailing</strong> for Two or Six at Chicago Sailboat Charters (Up to 50% Off)
Semi-Private or Private Luxury First-Class Sailing for Two or Six at Chicago Sailboat Charters (Up to 50% Off)

Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and stunning views

North end of Belmont Harbor, outside the H dock gate 6.5 mi
$199 $109
(45)
45% discount_off
One or Two Three-Hour <strong>Sailing</strong> Lessons at Sailboat-X.com, Valid 5/1/19–10/25/19 (Up to 55% Off)
One or Two Three-Hour Sailing Lessons at Sailboat-X.com, Valid 5/1/19–10/25/19 (Up to 55% Off)

Certified instructor leads on-the-water classes in which participants are taught how to rig the boat, trim the sails, and take the helm

Gold Coast-Chicago 3.1 mi
$125 $58
(68)
54% discount_off
Private Lakefront <strong>Sailing</strong> Tours with Windy City <strong>Sailing</strong> (Up to 31% Off)
Private Lakefront Sailing Tours with Windy City Sailing (Up to 31% Off)

Licensed captains charter along the Chicago lakefront in Lake Michigan

Chicago 6.5 mi
$600 $414
(37)
31% discount_off
Private Day <strong>Sailing</strong> Excursion on Lake Michigan
Private Day Sailing Excursion on Lake Michigan

The Loop 2.6 mi
10+ bought
$389.76
Private Morning Sail on Lake Michigan
Private Morning Sail on Lake Michigan

The Loop 2.6 mi
$389.76
One or Two 3-Hour Semi-Private <strong>Sailing</strong> or Racing Lessons at 3rd Coast Cruising (Up to 72% Off)
One or Two 3-Hour Semi-Private Sailing or Racing Lessons at 3rd Coast Cruising (Up to 72% Off)

Future sailors lean how to operate the boat safely during comprehensive sailing lessons

The Loop 2.7 mi
$300 $87
(20)
71% discount_off
Private Chicago Sunset Sail on Lake Michigan
Private Chicago Sunset Sail on Lake Michigan

Chicago
$389.76
Private Navy Pier Fireworks Sail in Chicago
Private Navy Pier Fireworks Sail in Chicago

Chicago
$445.76
$26 for Daytime or Sunset Cruise with Three Drinks for One from Tall Ship Red Witch ($41 Value)
$26 for Daytime or Sunset Cruise with Three Drinks for One from Tall Ship Red Witch ($41 Value)

Passengers relax on Kenosha’s wooden tall ship while enjoying their drinks

Kenosha Harbor, South Seawall
$41 $26
(127)
37% discount_off
Private Weekend <strong>Sailing</strong> Charter
Private Weekend Sailing Charter

Chicago
1 bought
$450
Memorial Day Weekend Booze Cruise from Yacht Party Chicago, May 24–27 (Up to 65% Off). Six Options Available.
Memorial Day Weekend Booze Cruise from Yacht Party Chicago, May 24–27 (Up to 65% Off). Six Options Available.

Guests can celebrate Memorial Day, partying to the music played by a live DJ on a three-story, 140-foot yacht

Dusable Harbor 3.2 mi
$57.25 $20
(923)
65% discount_off
Yacht Party Chicago's Memorial Day Weekend Booze Cruises - Friday, May 24, 2019 / 11:59pm (Boarding Begins at 11:30pm)
NEW NEW
Yacht Party Chicago's Memorial Day Weekend Booze Cruises - Friday, May 24, 2019 / 11:59pm (Boarding Begins at 11:30pm)

Near North Side 3.7 mi
$50 $27.50
45% discount_off
One Ticket for Friday and Saturday Booze Cruises from Yacht Party Chicago, May 10–18 (Up to 56% Off)
One Ticket for Friday and Saturday Booze Cruises from Yacht Party Chicago, May 10–18 (Up to 56% Off)

Participants take in breathtaking views of the Chicago skyline and dance to live DJ music as they cruise Lake Michigan on a yacht

Dusable Harbor 3.2 mi
$57.25 $25
(923)
56% discount_off
90-Minute Architectural Boat Tour for One or Two at Chicago Line Cruises (Up to 35% Off)
BEST OF GROUPON BEST OF GROUPON
90-Minute Architectural Boat Tour for One or Two at Chicago Line Cruises (Up to 35% Off)

Award-winning docents present Chicago’s most iconic architectural sites during 90-minute river cruise

Chicago Line Cruises 3.3 mi
$44 $29
(2932)
34% discount_off
Architecture Boat Tour for One or Two from Shoreline Sightseeing (Up to 31% Off)
BEST OF GROUPON BEST OF GROUPON
Architecture Boat Tour for One or Two from Shoreline Sightseeing (Up to 31% Off)

Participants can admire over 40 Chicago landmarks from the perspective of all three branches of the Chicago River

Multiple Locations 3.0 mi
$41.44 $29
(2157)
30% discount_off
"Pier Pressure" Memorial Weekend White Yacht Party - Sunday, May 26, 2019 / 11:00pm
"Pier Pressure" Memorial Weekend White Yacht Party - Sunday, May 26, 2019 / 11:00pm

Downtown 3.8 mi
$25 $17
32% discount_off
Rock the Yacht: Memorial Weekend Yacht Party - Sunday, May 26, 2019 / 6:30pm (Boarding Begins at 6:00pm)
Rock the Yacht: Memorial Weekend Yacht Party - Sunday, May 26, 2019 / 6:30pm (Boarding Begins at 6:00pm)

Downtown 3.8 mi
$30 $19.75
20+ bought
34% discount_off
Chicago-Lincoln Park Indoor Skydiving Experience
Chicago-Lincoln Park Indoor Skydiving Experience

Goose Island 3.8 mi
440+ bought
$76.25
Booze Cruises on Lake Michigan
Booze Cruises on Lake Michigan

Dusable Harbor 3.2 mi
$50 $32
40+ bought
36% discount_off
Chicago River Boat Architecture Tour
Chicago River Boat Architecture Tour

The Loop 2.1 mi
6 bought
$48
Memorial Day Fireworks Cruise - Saturday, May 25, 2019 / 9:00pm
Memorial Day Fireworks Cruise - Saturday, May 25, 2019 / 9:00pm

Downtown Chicago 3.2 mi
$100 $60
40% discount_off
Chicago by Night Cruise
Chicago by Night Cruise

The Loop 3.0 mi
(8)
$38
Dinner Cruises on Spirit of Chicago (Up to 27% Off). Five Options Available.
Dinner Cruises on Spirit of Chicago (Up to 27% Off). Five Options Available.

During the dinner cruise, guests have a chance to admire the shoreline of Lake Michigan while tasting buffet-style entrees and dancing

Navy Pier 3.6 mi
$108.66 $79
20+ bought
27% discount_off
Axe Throwing at BATL - The Backyard Axe Throwing League in Chicago
Axe Throwing at BATL - The Backyard Axe Throwing League in Chicago

Northwest Side 8.8 mi
70+ bought
$22.22
$29 for a Party or Individual Discovery Dive at Learn Scuba Chicago ($75 Value)
$29 for a Party or Individual Discovery Dive at Learn Scuba Chicago ($75 Value)

Exploratory dives for beginners led by dive expert Captain Bob

Multiple Locations 1.5 mi
$75 $29
(125)
61% discount_off
2019 Family Easter Cruise
2019 Family Easter Cruise

The Loop 3.2 mi
$50 $32
10+ bought
36% discount_off
Aqua Water Trike Rentals
Aqua Water Trike Rentals

Douglas 2.2 mi
20+ bought
$13.50
$119 for Two-Hour Electric Boat Rental from Chicago Electric Boat Company ($300 Value)
$119 for Two-Hour Electric Boat Rental from Chicago Electric Boat Company ($300 Value)

Comfortable and easy to navigate boats that give their crew and passengers the opportunity to look at Chicago from a new perspective

Near North Side 2.8 mi
$300 $119
(1026)
60% discount_off
Cinco de Mayo Booze Cruise on Lake Michigan
Cinco de Mayo Booze Cruise on Lake Michigan

The Loop 3.2 mi
$50 $27.50
8 bought
45% discount_off

Groupon Guide