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
    $136 nightly
    The price is $162 total per night from Jun 29 to Jun 30
    $162 total
    Jun 29 - Jun 30
    Total with taxes and fees
    8/10 Very Good! (10,265 reviews)
    Hyatt Regency O'Hare Chicago

    Hyatt Regency O'Hare Chicago

    9300 Bryn Mawr Ave Rosemont IL
    $135 nightly
    The price is $154 total per night from Jun 28 to Jun 29
    $154 total
    Jun 28 - Jun 29
    Total with taxes and fees
    8.8/10 Excellent! (2,666 reviews)
    The Chicago Hotel Collection - Magnificent Mile

    The Chicago Hotel Collection - Magnificent Mile

    166 E Superior Street Chicago IL
    $146 nightly
    The price is $174 total per night from Jun 30 to Jul 1
    $174 total
    Jun 30 - Jul 1
    Total with taxes and fees
    7.8/10 Good! (1,580 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
829 Vacation Homes
Lowest Price
$154
Highest Price
$462
Popular accommodation
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line, Historic Coach House in Evanston One Block to Beach and Close to Town and NU!, Charming Home in Portage Park, Chic Chicago Retreat (2-Bedroom Home) by RedAwning, Pleasant 3-bedroom house with occupied basement separate entrance., Spacious 2BR Group Stay near McCormick Place & Wintrust Arena, Cozy Home by O'Hare + EV Plug, King Comfort apartment, Quiet, Clean, AC & WiFi, Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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