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152 boats in Chicago, US
1 / 11
$180+/hour
INSTANT BOOK
Chicago, IL
5.0
(98 bookings)
3 - 8 hours rental • Captain optional
1 / 11
$250+/hour
INSTANT BOOK
Chicago, IL
5.0
(76 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
$195+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(144 bookings)
2 - 8 hours rental • Captain optional
1 / 32
$340+/hour
1 / 7
$153+/hour
Chicago, IL
5.0
(134 bookings)
3 - 6 hours rental • Captain optional
1 / 10
$200+/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 / 11
$242+/hour
INSTANT BOOK
Chicago, IL
5.0
(16 bookings)
3 - 6 hours rental • Captained
1 / 7
$150+/hour
INSTANT BOOK
Chicago, IL
5.0
(132 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 / 8
$246+/hour
Chicago, IL
2 - 6 hours rental • Captained
1 / 13
$215+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(173 bookings)
2 - 8 hours rental • Captain optional
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 / 11
$195+/hour
INSTANT BOOK
TOP OWNER
Chicago, IL
5.0
(9 bookings)
2 - 8 hours rental • Captain optional
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$180
Diversey Harbor 36' Sea Ray Floating Oasis
5.0
(98 bookings)
$180+
/hour
$250
Diversey Harbor's Gorgeous 48' Sea Ray Luxury Yacht
5.0
(76 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
$195
Sea Ray Sundancer 40ft – Spectacular Chicago Yacht Charter Experience
TOP OWNER
5.0
(144 bookings)
$195+
/hour
$340
The All-In, No-Compromise Experience
5.0
(16 bookings)
$340+
/hour
$153
Playpen bound on 25' Yamaha Jetboat!
5.0
(134 bookings)
$153+
/hour
$200
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
5.0
(25 bookings)
$200+
/hour
$276
4th hour FREE! $1000 Weekday Deals! Life Is Good on the water!
5.0
(55 bookings)
$276+
/hour
$242
Sleek 29ft Sport Cruiser | Playpen, Skyline, Sunset | Capt, Fuel Incl.
5.0
(16 bookings)
$242+
/hour
$150
New 27' Sea Ray Cruiser Yacht for Playpen Summertime
5.0
(132 bookings)
$150+
/hour
$165
Visit the Chicago Playpen! - 34' Rinker Fiesta Vee Yacht
TOP OWNER
4.9
(76 bookings)
$165+
/hour
$246
39' Beautiful Blue Sea Ray with Custom Bow Pad for Playpen Fun
$246+
/hour
$215
Sea Ray 39 Sundancer Yacht Cruise on Lake Michigan, Chicago
TOP OWNER
5.0
(173 bookings)
$215+
/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
$195
Sea Ray Sundancer 390 Yacht in Chicago
TOP OWNER
5.0
(9 bookings)
$195+
/hour