Book Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

Cozy Midway Home

Cozy Midway Home

2 out of 5
Chicago
Located in Chicago, this vacation home is within a 15-minute drive of McCormick Place and Soldier Field.
Cozy Midway Home
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Chicago
With a stay at this vacation home in Chicago (Uptown), you'll be within a 5-minute drive of Wrigley Field and Lake Michigan.
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!

Lincoln Park Living - Suite 2!

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Wrigley Field and Lake Michigan.
Lincoln Park Living - Suite 2!
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Great 3 bedroom rental unit near Logan Square

Great 3 bedroom rental unit near Logan Square

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 15-minute drive of Wrigley Field and United Center.
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chicago
Located in Chicago (Humboldt Park), this vacation home is within a 10-minute drive of United Center and Michigan Avenue.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!

Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!

Chicago
With a stay at this vacation home in Chicago (Bridgeport), you'll be within a 5-minute drive of McCormick Place and State Street.
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
New Humble Home! - Near Six Flags & Naval Base!!

New Humble Home! - Near Six Flags & Naval Base!!

North Chicago
When you stay at this vacation home in North Chicago, you'll be on a lake, within a 5-minute drive of Naval Base Great Lakes and Lake Michigan.
New Humble Home! - Near Six Flags & Naval Base!!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, a 2-minute drive from United Center and 6 minutes from Chicago Riverwalk.
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills

Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills

Waukegan
With a stay at this vacation home in Waukegan, you'll be a 4-minute drive from Lake Michigan and 8 minutes from Naval Base Great Lakes.
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
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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.

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
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

Top trending hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 28 Nov to 29 Nov
AU$154
includes taxes & fees
28 Nov - 29 Nov
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 22 Dec to 23 Dec
AU$189
includes taxes & fees
22 Dec - 23 Dec
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River Hotel
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 16 Dec to 17 Dec
AU$297
includes taxes & fees
16 Dec - 17 Dec
With a stay at The Westin Michigan Avenue Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 6 minutes by foot from Lake ...
The Westin Michigan Avenue Chicago
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Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 22 Dec to 23 Dec
AU$172
includes taxes & fees
22 Dec - 23 Dec
With a stay at Club Quarters Hotel, Central Loop, Chicago, you'll be centrally located in Chicago, within a 5-minute walk of State Street and Willis Tower.
Club Quarters Hotel, Central Loop, 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.

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^Subject to availability and chosen travel dates.