Book Holiday Homes in Chicago
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We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Chicago
Cozy Midway Home
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
New Humble Home! - Near Six Flags & Naval Base!!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Chicago Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chicago vacation homes are the perfect way for you to wing it.
Holiday houses in Chicago let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chicago in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chicago adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chicago with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chicago vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chicago Holiday Homes essential information
Accommodation | 678 Holiday Homes |
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Lowest Price | AU$154 |
Highest Price | AU$297 |
Popular accommodation | Cozy Midway Home , Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!, Lincoln Park Living - Suite 2!, Great 3 bedroom rental unit near Logan Square, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!, New Humble Home! - Near Six Flags & Naval Base!!, Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design, Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills |
Holiday Homes in Chicago
Top Locations for Holiday Homes in Chicago
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Congress Plaza Hotel
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The Westin Michigan Avenue Chicago
Club Quarters Hotel, Central Loop, Chicago
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**Terms and Conditions apply.
^Subject to availability and chosen travel dates.