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
    $179 nightly
    The price is $210 total per night from Jul 27 to Jul 28
    $210 total
    Jul 27 - Jul 28
    Total includes taxes and fees
    7.8/10 Good! (8,936 reviews)
    InterContinental Chicago Magnificent Mile by IHG

    InterContinental Chicago Magnificent Mile by IHG

    505 N Michigan Ave, Chicago, IL
    $231 nightly
    The price is $266 total per night from Aug 10 to Aug 11
    $266 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    9/10 Wonderful! (2,026 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl, Chicago, IL
    $151 nightly
    The price is $178 total per night from Aug 10 to Aug 11
    $178 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    8.8/10 Excellent! (2,428 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
931 Vacation Homes
Lowest Price
$178
Highest Price
$591
Popular accommodation
Clarendon Hills Top Floor, Lincoln Park Living - Suite 2!, Great 3 bedroom rental unit near Logan Square, Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, 4BR Retreat w/ Theater, Game Room & Backyard, Cheerful 4 bedroom smart home w/ indoor fireplace, Cozy 3-bedroom house in family-oriented Melrose Park., SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE, Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square