Sailing in Chicago, IL


Private Luxury Yacht Charter from Celestial Sails (Up to 50% Off). Two Options Available.
Private Luxury Yacht Charter from Celestial Sails (Up to 50% Off). Two Options Available.

Clients sail along Chicago’s beautiful Skyline on Lake Michigan aboard a luxurious 44’ Beneteau Oceanis

Chicago 2.7 mi
$750.00 $399.00
(13)
47% discount_off
<strong>Sailing</strong> Cruise from ChicaGo By Boat (Up to 40% Off)
Sailing Cruise from ChicaGo By Boat (Up to 40% Off)

Groups set sail with a master mariner on private charters that are complete with custom furnishings and a Bluetooth-compatible stereo system

Burnham Harbor 2.1 mi
$300.00 $179.00
(8)
40% discount_off
$75 for Wednesday Night Fireworks Cruise for One with Chicago <strong>Sailing</strong> ($100.80 Value)
$75 for Wednesday Night Fireworks Cruise for One with Chicago Sailing ($100.80 Value)

Guests are invited to admire Chicago’s skyline from a comfortable sailboat during an evening cruise

Lakeview 6.7 mi
$100.80 $75.00
1 bought
26% discount_off
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)

Licensed captains charter along the Chicago lakefront in Lake Michigan

Chicago 6.5 mi
$600.00 $425.00
(2)
29% 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
Rock the Yacht: Midnight Yacht Party - June 22, 2019 @ 11:55pm (Departing at 1:00am)
Rock the Yacht: Midnight Yacht Party - June 22, 2019 @ 11:55pm (Departing at 1:00am)
Downtown 3.8 mi
$41.80 $30.00
190+ bought
28% discount_off
Monday or Tuesday Night Happy Hour Sunset Party Cruise for 1, 2, or 4 (Up to 72% Off)
Monday or Tuesday Night Happy Hour Sunset Party Cruise for 1, 2, or 4 (Up to 72% Off)

Guests board a luxurious 400 capacity yacht and dance the night away while sipping on drinks and listening to great music

DuSable Harbor 3.2 mi
$32.00 $9.00
(614)
72% discount_off
Tuesday Night Sunset & Happy Hour Cruise
Tuesday Night Sunset & Happy Hour Cruise
DuSable Habor 3.2 mi
$25.00 $7.50
110+ bought
70% discount_off
Booze Cruises On Lake Michigan and Chicago River
Booze Cruises On Lake Michigan and Chicago River
The Loop 3.2 mi
$40.00 $26.25
10+ bought
34% discount_off
$35 for One General Admission Ticket to Lit on the Lake Yacht Party on Saturday, June 29/30 ($45 Value)
$35 for One General Admission Ticket to Lit on the Lake Yacht Party on Saturday, June 29/30 ($45 Value)

A three-hour cruise treats passengers to majestic views and a party led by DJs

Anita Dee Yacht Charters 3.2 mi
$45.00 $35.00
(194)
22% discount_off
Chicago Oktoberfest Cruise: Beer, Brats, and Boats
Chicago Oktoberfest Cruise: Beer, Brats, and Boats
Chicago
$66.08
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)

Chicago river tour paired with architecture and history lessons about the city’s most popular landmarks

Chicago 1.7 mi
$49.00 $29.00
(978)
41% discount_off
Chicago River and Lake Architecture Tour or Seadog Extreme Thrill Ride from Seadog Cruises (Up to 30% Off)
Chicago River and Lake Architecture Tour or Seadog Extreme Thrill Ride from Seadog Cruises (Up to 30% Off)

Speedboats zip past famed Chicago landmarks along the lakefront and river; informative narration on city’s history and architecture

Navy Pier 3.6 mi
$48.66 $34.00
(6733)
30% discount_off
90-Minute Architectural Boat Tour for Two from Chicago Line Cruises (Up to 27% Off). Two Options Available.
90-Minute Architectural Boat Tour for Two from Chicago Line Cruises (Up to 27% Off). Two Options Available.

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

Near North Side 3.3 mi
$88.00 $64.00
(3155)
27% discount_off
July 3rd & July 4th Afternoon, Sunset, & Fireworks Booze Cruises (Up to 70% Off).
July 3rd & July 4th Afternoon, Sunset, & Fireworks Booze Cruises (Up to 70% Off).

Participants can spend July 3rd & 4th on a yacht enjoying the amazing Chicago skyline, cocktails and great music

DuSable Harbor 3.2 mi
$64.00 $19.00
60+ bought
70% discount_off
Chicago River Boat Architecture Tour
Chicago River Boat Architecture Tour
Chicago 2.1 mi
120+ bought
$48.00
TikiBoat Cruise at Chicago TikiBoat (Up to 55% Off). Two Options Available.
TikiBoat Cruise at Chicago TikiBoat (Up to 55% Off). Two Options Available.

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 Chicago 2.6 mi
$893.00 $399.00
(22)
55% discount_off
at (Up to 72% Off)
at (Up to 72% Off)

Customers can enjoy BYOB party at 32-foot Polynesian themed pontoon that features water slide, premium sound system and private bathroom

Grant Park 2.9 mi
$1,050.00 $289.00
(22)
72% discount_off
Three-Hour Boat Rental at Party on Boats (Up to 72% Off). Three Options Available.
Three-Hour Boat Rental at Party on Boats (Up to 72% Off). Three Options Available.

Customers can enjoy the experience of taking a trip on a rented party boat with the guidance of licensed captain and explore the coast

Chicago 8.4 mi
$1,630.00 $459.00
(5)
72% discount_off
Chicago Riverwalk to Chinatown Boat Tour - Any Saturday Through October 3, 2019
Chicago Riverwalk to Chinatown Boat Tour - Any Saturday Through October 3, 2019
Near North Side 2.8 mi
$85.00 $42.00
6 bought
51% discount_off
Private Boat Rental for up to 20 Guests, Valid Weekday or Friday-Sunday from Chicago Pedal Boats (Up to 16% Off)
Private Boat Rental for up to 20 Guests, Valid Weekday or Friday-Sunday from Chicago Pedal Boats (Up to 16% Off)

Up to 20 friends can enjoy fun abord and explore beautiful lakrefront of Chicago River

Grant Park 2.8 mi
$750.00 $629.00
1 bought
16% discount_off
Shuttle Ferry Tickets from Port of Blarney to Blarney Island (Up to 50% Off). Three Options Available.
Shuttle Ferry Tickets from Port of Blarney to Blarney Island (Up to 50% Off). Three Options Available.

Participants get to enjoy boating bar with live music and variety of drinks

Antioch 47.6 mi
$32.00 $16.00
(54)
50% discount_off
Chicago Lake and River Architecture Tour
Chicago Lake and River Architecture Tour
Chicago
120+ bought
$39.00
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

Lakeview Manor Apartments
$630.00 $229.00
(44)
64% discount_off
Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!
Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!
Chicago
4 bought
$299.00
Chicago River Fireworks Cruise
Chicago River Fireworks Cruise
Chicago
1 bought
$35.00
Rock the Yacht: Midnight IndepenDANCE Party - Wednesday, Jul 3, 2019 / 11:59pm (Boarding Begins at 11:30pm)
Rock the Yacht: Midnight IndepenDANCE Party - Wednesday, Jul 3, 2019 / 11:59pm (Boarding Begins at 11:30pm)
Near North Side 3.6 mi
$42.19 $24.75
30+ bought
41% discount_off
July 3rd, 4th, & 5th Booze Cruises on Lake Michigan from Yacht Party Chicago (Up to 75% Off)
July 3rd, 4th, & 5th Booze Cruises on Lake Michigan from Yacht Party Chicago (Up to 75% Off)

Guests celebrate the holiday on a 3-story luxury yacht while enjoying views of the Chicago Skyline and dancing to live DJs

Downtown Chicago 3.2 mi
$59.72 $15.00
(999)
75% discount_off
Two-Hour Sunset Cruise for One, Two, or Four at Chicago Cruise Tickets on Monday or Tuesday (Up to 71% Off)
Two-Hour Sunset Cruise for One, Two, or Four at Chicago Cruise Tickets on Monday or Tuesday (Up to 71% Off)

During the sunset tour guests may admire the views of Chicago skyline and dance to the latest hits on one of the four decks

Navy Pier 3.6 mi
$25.00 $8.00
(801)
68% discount_off
Dinner Cruise on Odyssey Lake Michigan (Up to 40% Off). Four Options Available.
Dinner Cruise on Odyssey Lake Michigan (Up to 40% Off). Four Options Available.

Passengers admire Chicago’s skyline through large windows during elegant evening cruises, completed with a three-course meal

Navy Pier 3.6 mi
$156.26 $94.00
(1440)
40% discount_off