Compare West Side Houseboat Rentals

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Featured Houseboats in West Side

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in West Side

    Crowne Plaza Chicago West Loop by IHG

    Crowne Plaza Chicago West Loop by IHG

    25 South Halsted Street Chicago IL
    $88 nightly
    The price is $104 total per night from Jan 15 to Jan 16
    $104 total
    Jan 15 - Jan 16, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,761 reviews)
    Holiday Inn & Suites Chicago - Downtown by IHG

    Holiday Inn & Suites Chicago - Downtown by IHG

    506 West Harrison Street Chicago IL
    $107 nightly
    The price is $126 total per night from Dec 25 to Dec 26
    $126 total
    Dec 25 - Dec 26
    Total with taxes and fees
    8.2/10 Very Good! (1,013 reviews)
    Hyatt House Chicago Medical/University District

    Hyatt House Chicago Medical/University District

    1835 West Harrison Street Chicago IL
    $93 nightly
    The price is $109 total per night from Dec 22 to Dec 23
    $109 total
    Dec 22 - Dec 23
    Total with taxes and fees
    9/10 Wonderful! (1,252 reviews)

Houseboats

Book a houseboat in West Side
Take command of your next vacation…by taking the helm of a houseboat! Why debate over whether to stay home or go to the coast? A West Side houseboat rental lets you do both. It’s especially ideal if you’re traveling with a bunch of people, whether it’s family or friends, because it blends all the comfort of a “staycation” at home with adventure on the high seas. When you book through Orbitz, you’ll have everything you need to captain your new vacation home.

West Side houseboat vacations for everyone
Gather everyone you know, because most houseboats can sleep over 10 people while maintaining a cozy, small-house feel—without feeling cramped. There are showers and kitchens on almost every house boat, and some vessels come with hot tubs, wet bars and multiple TVs. Take your houseboat out to a particular spot in the water, or kick off a proper West Side adventure and travel from port to port. Your on-board crew will be so impressed with this unique vacation, they’ll probably start calling you “Skipper.” 

They’ll be even more impressed with the luxury house boats that are available. Think stunning décor, gorgeous artwork and even fireplaces for cool evenings on the water. Some even have glass bottoms so you can look right into the water beneath you.

When you want to give your sea legs a break, come ashore and do some sightseeing in West Side. Snap up a meal at one of the local restaurants, or do a little grocery shopping so you can cook once you’re back on the water. And don’t forget to look into fishing permits—there’s nothing like cooking up fresh-caught fish to really complete your houseboat experience. 

West Side Houseboats essential information

Accommodation
1 Houseboats
Lowest Price
$104
Highest Price
$278
Popular accommodation
Terrific 1-bedroom boat in Chicago

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