Sailing in Chicago, IL


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 • 2.4 mi
$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 • 2.4 mi
$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)

$189 for two three-hour introductory sailing or racing lessons ($600 value).

DuSable Harbor • 3 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 • 3 mi
70+ bought
$300 $99
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 • 3.1 mi
8 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 • 3.1 mi
8 bought
$125 $66
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: Monday - Friday .

North Side • 7.1 mi
$600 $425
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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 • 7.1 mi
$600 $425
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 (Two People).

31st Street Harbor • 2.4 mi
$437 $189
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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 • 2.4 mi
$437 $189
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 • 49.4 mi
9 bought
$299 $149
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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 • 49.4 mi
9 bought
$299 $149
image for United We Rock: Styx/REO Speedwagon with Don Felder on Saturday, July 1, at 7 p.m.
TRENDING
United We Rock: Styx/REO Speedwagon with Don Felder on Saturday, July 1, at 7 p.m.

Classic rock titans treats fans to mega-hits such as “Keep on Loving You” and “Renegade”; The Eagles’ Don Felder opens

Hollywood Casino Amphitheatre • 22.1 mi
240+ bought
$35.75 $15
View Deal
image for United We Rock: Styx/REO Speedwagon with Don Felder on Saturday, July 1, at 7 p.m.
TRENDING
United We Rock: Styx/REO Speedwagon with Don Felder on Saturday, July 1, at 7 p.m.
Hollywood Casino Amphitheatre • 22.1 mi
240+ bought
$35.75 $15
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 • 3.7 mi
70+ bought
$300 $139
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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 • 3.7 mi
70+ bought
$300 $139
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 • 2.8 mi
10+ bought
$780 $315
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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 • 2.8 mi
10+ 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 • 2.9 mi
$616 $259
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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 • 2.9 mi
$616 $259
image for Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
TRENDING
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
30+ bought
$630 $229
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image for Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
TRENDING
Three or Four-Night Cabin Stay and Daily Boat Rental for Two People at Gold Mine Camp (Up to 64% Off)
Gold Mine Camp
30+ bought
$630 $229
image for GA for Tickets for St. Patrick's Day Booze Cruise on 3/4, 3/11, 3/17, or 3/18 (Up to 59% Off)
GA for Tickets for St. Patrick's Day Booze Cruise on 3/4, 3/11, 3/17, or 3/18 (Up to 59% Off) at Yacht Party Chicago

Attendees celebrate St. Patrick’s Day on a luxury yacht while catching stunning views and dancing to music played by a DJ

Boarding at DuSable Harbor • 3.2 mi
90+ bought
$55.59 $25
View Deal
image for GA for Tickets for St. Patrick's Day Booze Cruise on 3/4, 3/11, 3/17, or 3/18 (Up to 59% Off)
GA for Tickets for St. Patrick's Day Booze Cruise on 3/4, 3/11, 3/17, or 3/18 (Up to 59% Off) at Yacht Party Chicago
Boarding at DuSable Harbor • 3.2 mi
90+ bought
$55.59 $25
image for One Booze Cruise Ticket for April 15, April 21, or April 28 at Yacht Party Chicago (Up to 50% Off)
One Booze Cruise Ticket for April 15, April 21, or April 28 at Yacht Party Chicago (Up to 50% 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 • 3.2 mi
5 bought
$50 $25
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image for One Booze Cruise Ticket for April 15, April 21, or April 28 at Yacht Party Chicago (Up to 50% Off)
One Booze Cruise Ticket for April 15, April 21, or April 28 at Yacht Party Chicago (Up to 50% Off)
Boarding at DuSable Harbor • 3.2 mi
5 bought
$50 $25
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 • 3 mi
$900 $500
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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 • 3 mi
$900 $500
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 • 33.3 mi
$499 $270
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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 • 33.3 mi
$499 $270
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 One.

Chicago • 3.1 mi
4 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 • 3.1 mi
4 bought
$125 $66
image for $6 for Two Murder Mystery Party Games of Your Choice from Clean Murder Mysteries ($12 Value)
$6 for Two Murder Mystery Party Games of Your Choice from Clean Murder Mysteries ($12 Value)

Add an extra element of suspense to any party – band together and solve the mystery before time runs out

10+ bought
$12 $6
View Deal
image for $6 for Two Murder Mystery Party Games of Your Choice from Clean Murder Mysteries ($12 Value)
$6 for Two Murder Mystery Party Games of Your Choice from Clean Murder Mysteries ($12 Value)
10+ bought
$12 $6
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
2 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
2 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
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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
image for Party-Bus Rental or SUV Transportation from Rokstars Chicago (Up to 46% Off). Four Options Available.
Party-Bus Rental or SUV Transportation from Rokstars Chicago (Up to 46% Off). Four Options Available.

Celebrate any occasion with up to 24 people on a rented party bus for three, four, or five hours, or get where you need to go in an SUV

Chicago
4 bought
$500 $299
View Deal
image for Party-Bus Rental or SUV Transportation from Rokstars Chicago (Up to 46% Off). Four Options Available.
Party-Bus Rental or SUV Transportation from Rokstars Chicago (Up to 46% Off). Four Options Available.
Chicago
4 bought
$500 $299
image for Free Kid's Event: South Side Irish St. Patrick's Day Parade March 12th
NEW
Free Kid's Event: South Side Irish St. Patrick's Day Parade March 12th

Watch and listen to traditional Irish music, dancing, and festivities at this parade, which has been an annual event for over 35 years

South Side • 5.3 mi
Claim for Free
View Deal
image for Free Kid's Event: South Side Irish St. Patrick's Day Parade March 12th
NEW
Free Kid's Event: South Side Irish St. Patrick's Day Parade March 12th
South Side • 5.3 mi
Claim for Free
image for Knowledge Beckom Presents Classic Hip Hop Lives feat AZ, MC EIHT & FREEWAY on Saturday, March 25, at 8 p.m.
NEW
Knowledge Beckom Presents Classic Hip Hop Lives feat AZ, MC EIHT & FREEWAY on Saturday, March 25, at 8 p.m.

Nas affiliate and lyrical 90’s rhymer AZ performs during an evening of classic hip-hop with MC EIHT and Freeway

Park West • 4.8 mi
$54.50 $38
View Deal
image for Knowledge Beckom Presents Classic Hip Hop Lives feat AZ, MC EIHT & FREEWAY on Saturday, March 25, at 8 p.m.
NEW
Knowledge Beckom Presents Classic Hip Hop Lives feat AZ, MC EIHT & FREEWAY on Saturday, March 25, at 8 p.m.
Park West • 4.8 mi
$54.50 $38
image for KIDZ BOP "Best Time Ever" Tour on July 30, at 3 p.m.
NEW
KIDZ BOP "Best Time Ever" Tour on July 30, at 3 p.m.

Billboard magazine’s #1 Kids’ Artist returns for a live concert featuring family-friendly covers of today’s biggest hits

Huntington Bank Pavilion at Northerly Island • 2.3 mi
$35.25 $18
View Deal
image for KIDZ BOP "Best Time Ever" Tour on July 30, at 3 p.m.
NEW
KIDZ BOP "Best Time Ever" Tour on July 30, at 3 p.m.
Huntington Bank Pavilion at Northerly Island • 2.3 mi
$35.25 $18
image for The Original Paint Nite at Local Bars (Up to 46% Off)
The Original Paint Nite at Local Bars (Up to 46% Off)

Paint Nite invites guests to break away from a typical night out with the perfect cocktail of creativity and conversation.

810+ bought
$45 $25
View Deal
image for The Original Paint Nite at Local Bars (Up to 46% Off)
The Original Paint Nite at Local Bars (Up to 46% Off)
810+ bought
$45 $25
image for Dreamboys (March 4–August 26)
Dreamboys (March 4–August 26)

Vegas-style male revue sees Josh Seiter of ABC’s The Bachelorette strip and dance alongside a cast of other hunks

LITE Chicago • 3.1 mi
70+ bought
$41.05 $19
View Deal
image for Dreamboys (March 4–August 26)
Dreamboys (March 4–August 26)
LITE Chicago • 3.1 mi
70+ bought
$41.05 $19
image for 2.5 Hour BYOB Painting Class for One or Two at Color Cocktail Factory (Up to 52% Off)
2.5 Hour BYOB Painting Class for One or Two at Color Cocktail Factory (Up to 52% Off)

Instructors with MFAs from the School of the Art Institute of Chicago lead laid-back BYOB painting classes at their studio space in Pilsen

Multiple Locations • 0.5 mi
5,000+ bought
$120 $58
View Deal
image for 2.5 Hour BYOB Painting Class for One or Two at Color Cocktail Factory (Up to 52% Off)
2.5 Hour BYOB Painting Class for One or Two at Color Cocktail Factory (Up to 52% Off)
Multiple Locations • 0.5 mi
5,000+ bought
$120 $58
image for Joey Fatts with D Savage on Friday, March 10, at 7 p.m.
Joey Fatts with D Savage on Friday, March 10, at 7 p.m.

Joey Fatts’s fresh rhymes bring with them the next wave of politically charged rap, incorporating current events and his own troubled past

Portage Theater • 8.8 mi
$17.77 $10
View Deal
image for Joey Fatts with D Savage on Friday, March 10, at 7 p.m.
Joey Fatts with D Savage on Friday, March 10, at 7 p.m.
Portage Theater • 8.8 mi
$17.77 $10
image for Merry Jane Presents Juicy J - The Rubba Band  Business Tour on Friday, March 17 at 8 p.m.
Merry Jane Presents Juicy J - The Rubba Band Business Tour on Friday, March 17 at 8 p.m.

Academy Award–winning rapper of Three 6 Mafia fame delivers hits such as “Bandz a Make Her Dance” alongside tracks from his latest album

House of Blues Chicago • 2.9 mi
170+ bought
$56.28 $40
View Deal
image for Merry Jane Presents Juicy J - The Rubba Band  Business Tour on Friday, March 17 at 8 p.m.
Merry Jane Presents Juicy J - The Rubba Band Business Tour on Friday, March 17 at 8 p.m.
House of Blues Chicago • 2.9 mi
170+ bought
$56.28 $40
image for $45 for a BYOB Build-A-Robot Date Night Event for Two at Robot City Workshop ($50 Value)
$45 for a BYOB Build-A-Robot Date Night Event for Two at Robot City Workshop ($50 Value)

During BYOB date nights held Thursday–Saturday, couples build robots and sip Metropolitan Brewing beers while a robot-themed movie plays

North Side • 6.3 mi
250+ bought
$45
View Deal
image for $45 for a BYOB Build-A-Robot Date Night Event for Two at Robot City Workshop ($50 Value)
$45 for a BYOB Build-A-Robot Date Night Event for Two at Robot City Workshop ($50 Value)
North Side • 6.3 mi
250+ bought
$45
image for $24 for $40 Groupon — The Tipsy Brush
$24 for $40 Groupon — The Tipsy Brush

From the merchant: We provide you with all art materials including a take home canvas. You bring your friends and your favorite wine!

Logan Square • 6.1 mi
640+ bought
$40 $24
View Deal
image for $24 for $40 Groupon — The Tipsy Brush
$24 for $40 Groupon — The Tipsy Brush
Logan Square • 6.1 mi
640+ bought
$40 $24
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