Cruise Chicago in Style

Premium Yachts

Experience Chicago from the water aboard our premium 40-foot yacht rentals, designed for comfort, style, and unforgettable moments. Perfect for upscale celebrations, relaxed cruising, or elevated entertaining, these professionally captained yachts offer exceptional value without compromising on space or luxury.

Choose a date to see pricing.

40′
FEET

13
PASSENGERS

CAPTAIN
INCLUDED

DUSABLE
HARBOR

40-Foot Yacht Rentals in Chicago

Our 40-foot yacht rentals in Chicago feature generous layouts with distinct spaces to relax and socialize. Stretch out on the bow sun pad at the front of the yacht or gather with your group on the expansive party deck at the rear, which comfortably accommodates over 11 guests. Whether you’re cruising the skyline, anchoring for a swim, or hosting an intimate celebration, these yacht-style powerboats offer more room, comfort, and flexibility than others in their class—making them a top choice for premium Chicago boat rentals.

What’s Included with Your Yacht Charter

40-foot spacious yachts

Accommodates up to 13 guests

Bow sun pad and large party deck

Spacious seating areas throughout

Swimming platform

Onboard bathroom

Upgraded audio system

Cooler provided

Why Chicago Sailboat & Yacht Charters?

Chicago Sailboat & Yacht Charters offers Chicago’s largest variety of captained charters for sailboats, yachts, and spacious big boats, accommodating groups of 1 to 36 people.

Enjoy daytime sailing, sunset cruises, swimming and sunbathing sails, or even witness the spectacular Navy Pier fireworks from our boats.

“The seven of us had a tremendous family outing with Captain Gregg on a beautiful, clean, well-appointed 40-ft powerboat rental from Chicago Sailboat Charters. It was a perfect day cruising up the lakefront, listening to our music, swimming off the back of the boat in “the playpen” traveling through the locks into the river and back again. Captain Gregg couldn’t have been a more courteous host for the day.”

Paul F.

How to Book Your Premium Yacht Charter

STEP 1: Use our online booking platform to view charter availability and pricing.

STEP 2: Once you select your charter, reserve and pay directly online in less than 60 seconds.

STEP 3: After booking, refer to your confirmation email for instructions on how to book a captain.

Premium Yachts

40-Foot Yacht Rentals in Chicago

What’s Included with Your Yacht Charter

Why Chicago Sailboat & Yacht Charters?

How to Book Your Premium Yacht Charter

Our Boat Rentals are perfect for:

Swimming and Playpen

Corporate Outings

Celebrations & Events

Chicago River Cruises

Firework Cruises

Daytime Sailing

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