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160 boats in Chicago, US
1 / 11
$195+/hour
INSTANT BOOK
Chicago, IL
5.0
(97 bookings)
3 - 8 hours rental • Captain optional
1 / 50
$275+/hour
Chicago, IL
5.0
(13 bookings)
2 - 4 hours rental • Captained
1 / 7
$192+/hour
Chicago, IL
5.0
(134 bookings)
3 - 6 hours rental • Captain optional
1 / 14
$250+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(272 bookings)
2 - 4 hours rental • Captained
1 / 11
$277+/hour
INSTANT BOOK
Chicago, IL
5.0
(16 bookings)
3 - 6 hours rental • Captained
1 / 10
$214+/hour
INSTANT BOOK
Chicago, IL
5.0
(25 bookings)
3 - 8 hours rental • Captain optional
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 / 8
$280+/hour
Chicago, IL
2 - 6 hours rental • Captained
1 / 7
$158+/hour
INSTANT BOOK
Chicago, IL
5.0
(131 bookings)
2 - 6 hours rental • Captain optional
1 / 18
$165+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
4.9
(76 bookings)
3 - 4 hours rental • Captain optional
1 / 21
$320+/hour
1 / 15
$195+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(53 bookings)
3 - 4 hours rental • Captain optional
1 / 17
$165+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(157 bookings)
3 - 4 hours rental • Captain optional
1 / 14
$600+/hour
INSTANT BOOK
1 / 13
$281+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(173 bookings)
2 - 8 hours rental • Captain optional
1 / 11
$250+/hour
INSTANT BOOK
Chicago, IL
5.0
(75 bookings)
3 - 8 hours rental • Captain optional
1 / 11
$281+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(9 bookings)
2 - 8 hours rental • Captain optional
Search as I move the map
$195
Diversey Harbor 36' Sea Ray Floating Oasis
5.0
(97 bookings)
$195+
/hour
$275
Navy Pier | Private Yacht | Captain Included
5.0
(13 bookings)
$275+
/hour
$192
Playpen bound on 25' Yamaha Jetboat!
5.0
(134 bookings)
$192+
/hour
$250
Maxum Yacht with Captain, Crew and Fuel Included - Burnham Harbor
TOP OWNER
5.0
(272 bookings)
$250+
/hour
$277
Sleek 29ft Sport Cruiser | Playpen, Skyline, Sunset | Capt, Fuel Incl.
5.0
(16 bookings)
$277+
/hour
$214
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
5.0
(25 bookings)
$214+
/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
$280
39' Beautiful Blue Sea Ray with Custom Bow Pad for Playpen Fun
$280+
/hour
$158
New 27' Sea Ray Cruiser Yacht for Playpen Summertime
5.0
(131 bookings)
$158+
/hour
$165
Visit the Chicago Playpen! - 34' Rinker Fiesta Vee Yacht
TOP OWNER
4.9
(76 bookings)
$165+
/hour
$320
Amazing Luxury Huge 40ft Cruiser Yacht
5.0
(47 bookings)
$320+
/hour
$195
Anchor in the Famous Chicago Playpen! 37' Rinker Fiesta Vee
TOP OWNER
5.0
(53 bookings)
$195+
/hour
$165
31' Beautiful Sea Ray Yacht Perfect for any Occasion - Enjoy Chicago!
TOP OWNER
5.0
(157 bookings)
$165+
/hour
$600
2015 Absolute 40 STL Motor Yacht for rent
5.0
(16 bookings)
$600+
/hour
$281
Sea Ray 39 Sundancer Yacht Cruise on Lake Michigan, Chicago
TOP OWNER
5.0
(173 bookings)
$281+
/hour
$250
Diversey Harbor's Gorgeous 48' Sea Ray Luxury Yacht
5.0
(75 bookings)
$250+
/hour
$281
Sea Ray Sundancer 390 Yacht in Chicago
TOP OWNER
5.0
(9 bookings)
$281+
/hour