The Windy City, Chicago, is one of the most populated and most popular cities in the U.S. With a rich history, beautiful geographic location and a culturally diverse population, Chicago attracts thousands of visitors each year. Museums, award-winning restaurants, craft breweries, bars, nightclubs, parks, sports arenas, shopping outlets, aquariums, art galleries and a ton of other attractions are on offer here. Whether you are in the city to check out The Magnificent Mile, take the Architecture River Cruise or take in panoramic views of the city from SkyDeck Chicago, you need a comfortable place to rest your head at the end of the day. Stay at a unique accommodation in the form of a houseboat and experience life on the water. To know more, check out our suggestions to rent a boat in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on December 24, 2024.
1. Compact houseboat close to downtown (from USD 235)
Experience a unique lodging experience in downtown Chicago’s Montrose Harbor on board this compact houseboat on the water. The houseboat has a cosy living area, comfortable bedroom, kitchenette, and half bath. Private bathrooms with showers can be accessed just four docks away. Views of the city skyline can be enjoyed from the boat. A seating area and barbecue grill on the dock are available to guests too. Navy Pier is at a short driving distance from the boat.
Paradise On The Water Houseboat
Address: 601 West Montrose Avenue
8.84 km (5.5 mi) from Millennium Park
2. Classic sailboat with a lake view
Enjoy living the boat life on board this classic sailboat berthed in a well-protected marina in Chicago. The highlight of your stay will be the fantastic lake views that can be enjoyed from the deck. Additional salient features of the sailboat are a v-shaped berth that easily sleeps two guests and additional sleeping space in the living area. A bathroom is available on the boat, but guests will be provided with bathroom and shower codes that can be accessed off the dock, on land. The River Walk, Navy Pier, Millennium Park and several restaurants and shops are just a few minutes’ walk away.
Chicago, Illinois, United States
1.01 km (0.7 mi) from Millennium ParkTop guest reviews
Host:
charles was great host and very attentive to any issuesCleanliness:
private for the harbor it was very clean and spacious with good hot waterRead more reviewsAmenities & Room:
space heater took care of any chill at night
3. Beautiful sailboat offering sunset and skyline views
Hop aboard this beautiful boat that has everything you would expect in a classic sailboat. The interior of the boat has an elegant sailboat-style decor with a spacious living-cum-dining area, kitchen, two private cabins with plush bedding and two bathrooms. The outdoor cockpit area has plenty of deck space to experience breathtaking sunset and skyline views. Guests can also hire the boat for chartered cruises. Downtown Chicago, Navy Pier and other such attractions are at just a few minutes’ drive from the boat.
Chicago, Illinois, United States
5.39 km (3.4 mi) from Millennium Park
4. Cosy sailboat with gorgeous skyline views
Experience the boat life in this compact sailboat moored in a quiet harbour next to Chicago’s Museum Campus. The sailboat has all the amenities required for a comfortable vacation including a lounging and dining area, a functional kitchen, a half bath and cosy bedrooms. The best feature of the boat is the deck where you can relax and lounge about enjoying gorgeous skyline views. Bike paths, beaches, restaurants, bars, bike rentals, and showers are close by. The Field Museum is a mere 10-minute walk away.
Chicago, Illinois, United States
2.47 km (1.6 mi) from Millennium ParkTop guest reviews
Host:
great hoststhe boat and host were both greatbarbara is a great hostbarb was a great hostbarb and carlos were excellent hostsLocation:
it was a perfect location for the gameit's an easy fun walk to restaurants and breakfast joints museums millennium park etcsuper unique stay great location for mccormick place or soldier fieldunique experience perfect location fun fun funloved the boat and locationCleanliness:
nice boat very clean and great locationthe neighbors were friendly and the boat was clean and had a nice stereo systemRead more reviewsAmenities & Room:
we appreciated the breakfasts and the waterssleeping on a boat is a great alternative to a conventional apartment
5. Well-furnished cruiser near McCormick Place Convention Center
Aboard this 33-feet (10-metre) cruiser harboured on Lake Michigan, guests can live the marina life! The cruiser is tastefully furnished and comfortably sleeps four guests. There is a well-furnished salon, galley, full bath and sleeping berths with privacy curtains. Guests can take in the Chicago skyline views from the aft cockpit which converts to a sun pad. Access to grill, pool, picnic area, playground and members-only restrooms/showers is also provided to renters. The boat is a short walk to bike rentals and lakefront trails. McCormick Place Convention Center is just five minutes away.
Chicago, Illinois, United States
6.1 km (3.8 mi) from Millennium ParkTop guest reviews
Host:
joseph is so welcoming and kindjoseph is very friendly and helpfuljoseph was very accommodating and provided a great opportunity for a unique stay in chicagoLocation:
beautiful setting and convenient locationperfect place- secluded but close to downtownmy week in chicago was great you can not get a better location than this boatthank you very much best experience and locationgreat boat in a great locationRead more reviewsAmenities & Room:
there’s free washer/dryer on the facilities
Experience Chicago from the water!
Get a unique perspective and view of Chicago with a stay on a boat. With its convenient location right next to Lake Michigan and the availability of plenty of protected marinas, renting a boat for your stay in Chicago is very easy. On your next trip to the Windy City, be sure to check out our ‘Rent A Boat’ options in Chicago, Illinois.
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