Chicago Vacation Homes

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Featured Vacation Homes in Chicago

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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 Chicago

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL, 60605
    The price is $116 per night from Jan 2 to Jan 3
    $116
    per night
    Jan 2 - Jan 3
    3.7/5 Good! (3,829 reviews)
    The Whitehall Hotel

    The Whitehall Hotel

    105 E Delaware Pl, Chicago, IL, 60611
    The price is $84 per night from Dec 18 to Dec 19
    $84
    per night
    Dec 18 - Dec 19
    3.9/5 Good! (3,145 reviews)
    Eurostars Magnificent Mile

    Eurostars Magnificent Mile

    660 North State Street, Chicago, IL, 60654
    The price is $90 per night from Dec 4 to Dec 5
    $90
    per night
    Dec 4 - Dec 5
    4.1/5 Very Good! (1,836 reviews)

Chicago Vacation Homes

Book vacation homes in Chicago
Next time you take a group getaway top Chicago, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chicago vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chicago vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chicago; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chicago rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chicago is sure to be a winner.