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153 boats in Chicago, US
1 / 11
$250+/hour
INSTANT BOOK
Chicago, IL
5.0
(74 bookings)
3 - 8 hours rental • Captain optional
1 / 7
$156+/hour
INSTANT BOOK
Chicago, IL
5.0
(176 bookings)
2 - 8 hours rental • Captained
1 / 21
$275+/hour
INSTANT BOOK
Chicago, IL
4.9
(286 bookings)
2 - 8 hours rental • Captained
1 / 50
$275+/hour
Chicago, IL
5.0
(13 bookings)
2 - 4 hours rental • Captained
1 / 10
$212+/hour
INSTANT BOOK
Chicago, IL
5.0
(25 bookings)
3 - 8 hours rental • Captain optional
1 / 14
$250+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(272 bookings)
2 - 4 hours rental • Captained
1 / 8
$276+/hour
INSTANT BOOK
Chicago, IL
5.0
(55 bookings)
3 - 8 hours rental • Captain optional
1 / 12
$340+/hour
INSTANT BOOK
Chicago, IL
5.0
(18 bookings)
2 - 6 hours rental • Captained
1 / 11
$268+/hour
INSTANT BOOK
Chicago, IL
5.0
(16 bookings)
3 - 6 hours rental • Captained
1 / 21
$320+/hour
1 / 7
$158+/hour
INSTANT BOOK
Chicago, IL
5.0
(131 bookings)
2 - 6 hours rental • Captain optional
1 / 11
$525+/hour
1 / 28
$295+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(135 bookings)
3 - 8 hours rental • Captained
1 / 31
$300+/hour
Chicago, IL
5.0
(37 bookings)
2 - 6 hours rental • Captained
1 / 7
$192+/hour
Chicago, IL
5.0
(134 bookings)
3 - 6 hours rental • Captain optional
1 / 54
$195+/hour
TOP OWNER
Chicago, IL
5.0
(98 bookings)
3 - 8 hours rental • No captain
1 / 11
$180+/hour
INSTANT BOOK
Chicago, IL
5.0
(96 bookings)
3 - 8 hours rental • Captain optional
1 / 13
$282+/hour
Chicago, IL
5.0
(28 bookings)
3 - 6 hours rental • Captained
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$250
Diversey Harbor's Gorgeous 48' Sea Ray Luxury Yacht
5.0
(74 bookings)
$250+
/hour
$156
Godfrey Marine Sweetwater 22' Tritoon Charter with Licensed Captain
5.0
(176 bookings)
$156+
/hour
$275
44' Chris Craft Luxury Spacious Party Motor Yacht With Captain
4.9
(286 bookings)
$275+
/hour
$275
Navy Pier | Private Yacht | Captain Included
5.0
(13 bookings)
$275+
/hour
$212
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
5.0
(25 bookings)
$212+
/hour
$250
Maxum Yacht with Captain, Crew and Fuel Included - Burnham Harbor
TOP OWNER
5.0
(272 bookings)
$250+
/hour
$276
4th hour FREE! $1000 Weekday Deals! Life Is Good on the water!
5.0
(55 bookings)
$276+
/hour
$340
Classic 43ft Hatteras Motor Yacht with USCG Captain Included
5.0
(18 bookings)
$340+
/hour
$268
Sleek 29ft Sport Cruiser | Playpen, Skyline, Sunset | Capt, Fuel Incl.
5.0
(16 bookings)
$268+
/hour
$320
Amazing Luxury Huge 40ft Cruiser Yacht
5.0
(47 bookings)
$320+
/hour
$158
New 27' Sea Ray Cruiser Yacht for Playpen Summertime
5.0
(131 bookings)
$158+
/hour
$525
46' Prestige Flybridge Luxury Yacht!
4.8
(18 bookings)
$525+
/hour
$295
Cruisers Esprit 33ft – Victory at Sea Chicago Party Yacht Charter
TOP OWNER
5.0
(135 bookings)
$295+
/hour
$300
6 Passengers or Less this Yacht is Just Right for You!
20% discount.
5.0
(37 bookings)
$300+
/hour
$192
Playpen bound on 25' Yamaha Jetboat!
5.0
(134 bookings)
$192+
/hour
$195
23' Bayliner Motor Boat for rent at Downtown Chicago
TOP OWNER
5.0
(98 bookings)
$195+
/hour
$180
Diversey Harbor 36' Sea Ray Floating Oasis
5.0
(96 bookings)
$180+
/hour
$282
Sea Ray 370 Sundancer – Affordable Luxury Cruise w/ Floaty in Chicago
5.0
(28 bookings)
$282+
/hour