Limited availability
Some departure times on this date are still available.
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Some departure times on this date are still available.
Turn your Chicago boating experience into a party on the water with the Four Winns 225 Sundowner, a sleek 23-foot speed boat perfect for cruising the Chicago River, Lake Michigan, or heading to popular spots like the Playpen along Lake Shore Drive. With space for up to 6 guests, this boat is ideal for small group outings, sunset cruises, or watching spectacular fireworks on Wednesday and Saturday nights. Equipped with a big sound system and Bluetooth connectivity, you can set the perfect soundtrack for your adventure while relaxing on comfortable seating or enjoying the open deck. The boat also comes with inflatables, floats, and plenty of water toys to keep the fun going. Onboard Features & Equipment - Capacity: 6 guests - Cabins: 1 / Toilet: 1 - Leisure & Entertainment: Bluetooth, premium sound system, inflatables, floats, water toys - Guest Amenities: Cooler, washroom onboard - Safety Equipment: Life jackets (8), lifebuoys, fire extinguishers, first aid kit, flares, kill switch lanyard, medical supplies - Navigation & Accessories: Anchor & rode, bilge pumps, navigation lights, sound signals, VHF radio, PFDs, tool kit Perfect for architecture tours along the Chicago River, sunset cruises, or high-energy outings on Lake Michigan, the Four Winns 225 Sundowner delivers style, comfort, and excitement for an unforgettable Chicago boating adventure. Sun, music, city skyline, and lake vibes, your Chicago river or lake party starts here.

KM
Great experience with Samuel, looking forward to booking him again!
AK
He made my Birthday celebration!! Very recommend!
TF
Sam is the best!!! Book with him!!!
TM
We had an amazing experience with our captain, Samuel! He was professional, friendly, and made sure we had a great time from start to finish. Everything went smoothly, and we felt comfortable and well taken care of throughout the entire trip. Samuel made our time on the water in Chicago so much fun and truly memorable. We would definitely book with him again. Highly recommend!

Captain Samuel made our Chicago boat day one of the highlights of our trip. He was incredibly hospitable and flexible in accommodating our schedule, making the entire experience seamless and enjoyable. We would absolutely book with him again and highly recommend him to anyone visiting Chicago.

I love the water. Experienced Luxury Yacht Capitán. 7yrs. Great Lakes & Ocean experience.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 5 days before your trip.
Cancel before 5 days get 100%refund. Book an other day if weather not permitting. Starting time is starting time whether your late. I have all safety requirements. No red wine.