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Waukegan, Illinois Boat Rentals

Page 1 of 124 listings

27' Motor Yacht Charter in Waukegan, Illinois
Powerboats in Waukegan · 4 guests

27' Motor Yacht Charter in Waukegan, Illinois

New
$241/hour
Explore the Coast on the 27’ Bayliner Ciera Sunbridge
Powerboats in Waukegan · 4 guests

Explore the Coast on the 27’ Bayliner Ciera Sunbridge

New
$350/hour
SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
Sailing in Kenosha · 6 guests

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

New
$175/hour
Kenosha Fishing Charter on 32ft Luhrs Tournament Sportfish
Fishing in Kenosha · 6 guests

Kenosha Fishing Charter on 32ft Luhrs Tournament Sportfish

5.0
$90+/hour
Instant Book
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
Powerboats in Antioch · 8 guests

Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available

5.0
$100+/hour
Beautiful Deck Boat with captain on Lake Zurich
Powerboats in Lake Zurich · 6 guests

Beautiful Deck Boat with captain on Lake Zurich

New
$185/hour
2022 South Bay 24 foot Tritoon - rent by the day or week
Powerboats in Fox Lake · 14 guests

2022 South Bay 24 foot Tritoon - rent by the day or week

5.0
$145/hour
Twin engine 2023 Scarab Bowrider for Rent in Johnsburg, Illinois
Powerboats in Fox Lake · 7 guests

Twin engine 2023 Scarab Bowrider for Rent in Johnsburg, Illinois

5.0
$125/hour
Instant Book
40ft Chris Craft for Fishing or Cruising on Lake Michigan
Fishing in Racine · 6 guests

40ft Chris Craft for Fishing or Cruising on Lake Michigan

5.0
$145/hour
Instant Book
23ft tidewater  Boat Rental in Racine, Wisconsin
Powerboats in Racine · 4 guests

23ft tidewater Boat Rental in Racine, Wisconsin

New
$125/hour
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable
Events in Chicago · 8 guests

Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable

New
Snoozed - Active 02 Oct 2025
Oceanis 393 Beneteau Sailing Yacht Rental in Chicago
Sailing in Chicago · 10 guests

Oceanis 393 Beneteau Sailing Yacht Rental in Chicago

New
$275/hour
LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
Events in Chicago · 13 guests

LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

5.0
Superowner
Best of 2025
$250/hour
Flawless 2024 68' Sunseeker Manhattan
Events in Chicago · 12 guests

Flawless 2024 68' Sunseeker Manhattan

New
Snoozed - Active 02 Jan 2026
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
$349/hour
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Events in Chicago · 13 guests

44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available

5.0
Superowner
$575+/hour
46' Luxury Yacht! Price all inclusive!
Events in Chicago · 6 guests

46' Luxury Yacht! Price all inclusive!

5.0
$400/hour
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
$240/hour
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
$250/hour
35' Sea Ray SLX Motor Yacht Charter in Chicago
Events in Chicago · 13 guests

35' Sea Ray SLX Motor Yacht Charter in Chicago

5.0
$250/hour
31ft Cabin Cruiser Belmont Harbor location
Events in Chicago · 6 guests

31ft Cabin Cruiser Belmont Harbor location

New
$300/hour
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Events in Chicago · 20 guests

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

4.8
$1,500/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

4.8
$245/hour

Waukegan Reviews

  1. AX

    Andrew

    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    Shay and team were one of the best folks to charter in Chicago from. Along with the rapid responsiveness, the general helpfulness, and especially providing a captain priced for the charter, just made everything so much easier and funner!!

  2. Fenwa

    Fenwa

    Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

    Good experience and great service on the boat! Our captain and the staff were awesome! They really took care of us. Took photos, poured our drinks, just made sure we were having a good time.

  3. JR

    Jasmine

    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    This was a perfect boat for a day in the sun. I highly recommend using captain Joe as well. He made us feel very safe, was super knowledgeable and very down to earth. Great experience!

  4. JM

    Julie

    No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

    Great vessel. Everything we needed! Amazing deck hand and Captain (Georgia and Matt). They made our air and water show experience incredible!

  5. JB

    Joe

    2022 South Bay 24 foot Tritoon - rent by the day or week

    Took Joe’s boat out on the chain for the day and it was fantastic! There were 8 of us and still had plenty of room to move around and spread out. Communication was excellent and he met us in the morning to give an overview.

  6. Emily

    Emily

    44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available

    Captain Tim was amazing! He was super communicative, fun, patient, and just a great captain overall. Everybody had a great experience on the boat and absolutely loved it! The boat itself was also gorgeous. We would definitely book with Captain Tim again.