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
    $101 nightly
    The price is $118 total per night from Apr 1 to Apr 2
    $118 total
    Apr 1 - Apr 2
    Total with taxes and fees
    8/10 Very Good! (9,942 reviews)
    Embassy Suites by Hilton Chicago Downtown River North

    Embassy Suites by Hilton Chicago Downtown River North

    600 N State St Chicago IL
    $122 nightly
    The price is $143 total per night from Mar 19 to Mar 20
    $143 total
    Mar 19 - Mar 20
    Total with taxes and fees
    8.6/10 Excellent! (5,725 reviews)
    Hotel Riu Plaza Chicago

    Hotel Riu Plaza Chicago

    150 East Ontario Street Chicago IL
    $162 nightly
    The price is $190 total per night from Mar 24 to Mar 25
    $190 total
    Mar 24 - Mar 25
    Total with taxes and fees
    9.4/10 Exceptional! (3,511 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.

Chicago Vacation Homes essential information

Accommodation
822 Vacation Homes
Lowest Price
$118
Highest Price
$190
Popular accommodation
Great 3 bedroom rental unit near Logan Square, Spacious 3BR Duplex for Groups-Near Airport & Downtown-Cozy & Quiet, Wrigley Field/Lakeview -Entire Home- Large Groups!, Heart of the City Group Hub • Patio • Fireplace • Parking, Clarendon Hills Top Floor, Belmont House, Classy & Chic/walk to Wrigley Field, A Home Away From Home!, WINTER DISCOUNTED! Relax with family in a super Lux Custom SFH. West town., Historic luxury townhouse on Chicago's Gold Coast

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