Find the Best Boat Rentals and Yacht Charters in Chicago

Choose from 16 boats, Your Adventure Awaits
50' Luxury Yacht. Playpen, River cruises up to 12
14 Photos

50' Luxury Yacht. Playpen, River cruises up to 12

$1,600 ·
1-10 passengers
5.0/5 stars 15 · Captain Included
Chicago at it's finest aboard the 46' Great Laker
7 Photos

Chicago at it's finest aboard the 46' Great Laker

$1,600 ·
1-6 passengers
5.0/5 stars 3 · Captain Included
50 Ft PARTY BOAT (1 of 2) - Up to 12 Guests!
12 Photos

50 Ft PARTY BOAT (1 of 2) - Up to 12 Guests!

$850 ·
1-10 passengers
5.0/5 stars 8 · Captain Available
The Floating B&B
13 Photos

The Floating B&B

$2,450 ·
1-10 passengers
5.0/5 stars 3 · Captain Included
51' Sea Ray Sundancer powerboat
27 Photos

51' Sea Ray Sundancer powerboat

$1,950 ·
1-6 passengers
5.0/5 stars 5 · Captain Included
50 Ft PARTY BOAT (2 of 2) - Up to 12 Guests!
12 Photos

50 Ft PARTY BOAT (2 of 2) - Up to 12 Guests!

$850 ·
1-10 passengers
5.0/5 stars 1 · Captain Available
Playpen King
3 Photos

Playpen King

$2,250 ·
1-10 passengers
5.0/5 stars 1 · Captain Included
Brand New 3 Bedroom / 2 Bathroom 43' Yacht
7 Photos

Brand New 3 Bedroom / 2 Bathroom 43' Yacht

$3,800 ·
1-10 passengers
5.0/5 stars 1 · Captain Included
Adeline's Sea Moose, Chicago Yacht 68' Chris Craft
36 Photos

Adeline's Sea Moose, Chicago Yacht 68' Chris Craft

$6,000 ·
1-10 passengers
0.0/5 stars · Captain Included
Sophisticated Lady, Chicago 72' yacht 2 - 49 guest
17 Photos

Sophisticated Lady, Chicago 72' yacht 2 - 49 guest

$4,605 ·
1-10 passengers
0.0/5 stars · Captain Included
Cranchi 47 Luxury Cruiser
5 Photos

Cranchi 47 Luxury Cruiser

$2,250 ·
1-10 passengers
0.0/5 stars · Captain Included
Azimut 62 s
10 Photos

Azimut 62 s

$3,750 ·
1-10 passengers
5.0/5 stars 2 · Captain Included
Relax and Enjoy the Sun on a 50' Sea Ray
4 Photos

Relax and Enjoy the Sun on a 50' Sea Ray

$2,270 ·
1-6 passengers
0.0/5 stars · Captain Included
40' Luxury Yacht. Playpen, River cruises up to 6
5 Photos

40' Luxury Yacht. Playpen, River cruises up to 6

$1,800 ·
1-6 passengers
0.0/5 stars · Captain Included
Luxury Carver Yacht with upgraded sound system
15 Photos

Luxury Carver Yacht with upgraded sound system

$2,200 ·
1-10 passengers
0.0/5 stars · Captain Included
Last Nickel
6 Photos

Last Nickel

$2,900 ·
1-6 passengers
0.0/5 stars · Captain Included
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