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Lake Michigan, US Boat Rentals & Yacht Charters

4.9

(6,806 Reviews)

Page 4 of 15 • 355 listings

Powerboats in Michigan · 12 guests

MasterCraft X24 Wakeboard/Wakesurf /Foil/Tube or Hangout Up to 12 Guests

5.0

$295/hour

Limited Availability

Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0

Superowner

Best of 2026

$220/hour

Limited Availability

Powerboats in Chicago · 8 guests

Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain

4.4

$250/hour

Events in Chicago · 6 guests

Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

5.0

$375/hour

Limited Availability

Events in Chicago · 7 guests

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests

5.0

Superowner

$500+/hour

Limited Availability

Events in Chicago · 12 guests

46' Sunseeker Portofino Yacht in Chicago for Parties & Events

4.8

$250/hour

Events in Chicago · 13 guests

60ft Azimut Evolution Double Decker Yacht Charter in Chicago

5.0

Superowner

Best of 2026

$750+/hour

Limited Availability

Sailing in Chicago · 6 guests

Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

5.0

$450/hour

Limited Availability

Powerboats in Chicago · 16 guests

16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!

5.0

Superowner

Best of 2026

$650/hour

Limited Availability

Events in Chicago · 36 guests

No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

5.0

$793/hour

High Demand

Powerboats in Chicago · 10 guests

25ft Yamaha 252SE Jet Boat Charter in Chicago - Playpen Adventure

5.0

$245/hour

Limited Availability

Powerboats in Chicago · 20 guests

20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

5.0

Superowner

Best of 2026

$700/hour

Events in Chicago · 6 guests

"Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!

5.0

$350+/hour

Events in Chicago · 12 guests

Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago

5.0

$300/hour

High Demand

Events in Chicago · 12 guests

40’ Cruiser Yacht Charter for fun, music and you bring the action!

4.5

$300/hour

Limited Availability

Events in Chicago · 10 guests

33ft Bayliner Powerboat Charter in Chicago for 10 Guests

4.6

$300/hour

Powerboats in Michigan · 14 guests

22ft Bennington Tritoon for 14 pax on Glen Lake! Free delivery!

5.0

$125/hour

Limited Availability

Events in Chicago · 12 guests

Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht

5.0

Superowner

Best of 2026

$325/hour

Instant Book

High Demand

Events in Chicago · 20 guests

Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam

4.8

$1,500/hour

Overnight in New Buffalo · 4 guests

Boatel! Live aboard a 44ft Motor Yacht - New Buffalo, MI

5.0

Superowner

$22/hour

Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0

$210+/hour

Limited Availability

Events in Chicago · 12 guests

Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests

5.0

Superowner

Best of 2026

$160+/hour

Instant Book

Sailing in Chicago · 13 guests

Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

5.0

$440/hour

Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0

$140/hour

Top Destinations Nearby

Lake Michigan Reviews

Barb

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
The boat is exactly as listed. Had a great night out watching the navy pier fireworks. Communication was excellent. The weather wasn’t cooperating and the captain was quick to reach out with details. We ended up rescheduling twice. Chicago weather what are you going to do. But once we got in the boat everything was so lovely. And there is a boat dog named, Piper. Piper kept us all entertained! Highly recommend!
KG
Katie

No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
Our whole group had a great time with Captain Tim & Sunny. Martin’s communication leading up to the event was very helpful, informative, and timely. Weather wasn’t on our side but the team ensured we all had a blast on the river. We’d love to go again!
Carrie

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
What a Wonderful evening we had on the water with Nijole, her 1st mat (hubby) and precious little Piper "the pup". This sail boat is a MUST BOOK! Nijole's sailing abilities, great stories and knowledge of the water on and surrounding Lake Michigan are exemplar! We had such an incredible majestic peaceful evening on the water! Will be back on the HARMONY next Chicago Visit for Sure. Carrie, Kelly, Mike & Zac ( Naples, FL) :0)
CV
Camilla

No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
Our group had a wonderful day on the lake! The captain and the rest of the crew were welcoming, professional and communicative. I would highly recommend booking with them! We are already excited to book again next summer!
Elisabeth

Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests
Had a great time! Did get upgraded, so was not on this boat specifically for the actual charter but seemed like it would have been great! Would recommend to keep below 10 guests for space/moving around
Cheri Ann

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests
Chris and his lovely wife hosted my family of 6 on their vessel for the 4th of July. He stayed in constant communication before the trip and also discussed the weather. He offered ideas for the perfect 5 hours on the Lake, and was not wrong. The couple was the perfect host. Their boat was beautiful. They gave us the best day!