Book Holiday Homes in Northwest Chicago

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

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 Northwest Chicago

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 Michigan Avenue and Wrigley Field.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stunning / Spacious 6BD Home + garage - Bucktown!

Stunning / Spacious 6BD Home + garage - Bucktown!

Chicago
With a stay at this vacation home in Chicago (Bucktown), you'll be a 5-minute drive from Wrigley Field and 7 minutes from Michigan Avenue.
Stunning / Spacious 6BD Home + garage - Bucktown!
Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests

Aurora
Located in Aurora, this vacation home is within a 5-minute drive of Copley Memorial Hospital and Rush-Copley Medical Center.
Furnished Private home in Aurora sleeps 9 guests
Save an average of 15% on thousands of hotels when you're signed in
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 Chicago Riverwalk.
Great 3 bedroom rental unit near Logan Square
New Your Home Away From Home! - Near Great Lakes Naval Base!!

New Your Home Away From Home! - Near Great Lakes 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 Your Home Away From Home! - Near Great Lakes Naval Base!!
Belmont House, Classy & Chic/walk to Wrigley Field

Belmont House, Classy & Chic/walk to Wrigley Field

Chicago
With a stay at this vacation home in Chicago (Lakeview), you'll be a 2-minute drive from Wrigley Field and 6 minutes from Michigan Avenue.
Belmont House, Classy & Chic/walk to Wrigley Field
Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis

Chicago
Located in Chicago (North Park), this vacation home is within a 10-minute drive of Wrigley Field and Lake Michigan.
Chicago Riverhouse with private fenced in oasis
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Chicago
With a stay at this vacation home in Chicago (Humboldt Park), you'll be a 5-minute drive from United Center and 8 minutes from Chicago Riverwalk.
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Spacious 5-bedroom house with movie room, game room and more!

Spacious 5-bedroom house with movie room, game room and more!

Berwyn
Located in Berwyn, this vacation home is within a 15-minute drive of Millennium Park and United Center.
Spacious 5-bedroom house with movie room, game room and more!
Don't see what you're looking for?
See all available properties in Northwest Chicago
View all properties
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.

Northwest 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 Northwest Chicago vacation homes are the perfect way for you to wing it.

Holiday houses in Northwest 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 Northwest 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 Northwest Chicago adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Northwest 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 Northwest 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.

Northwest Chicago Holiday Homes essential information

Accommodation
407 Holiday Homes
Lowest Price
AU$85
Highest Price
AU$266
Popular accommodation
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Stunning / Spacious 6BD Home + garage - Bucktown!, Furnished Private home in Aurora sleeps 9 guests, Great 3 bedroom rental unit near Logan Square, New Your Home Away From Home! - Near Great Lakes Naval Base!!, Belmont House, Classy & Chic/walk to Wrigley Field, Chicago Riverhouse with private fenced in oasis, Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow, Spacious 5-bedroom house with movie room, game room and more!

Top trending hotels in Northwest Chicago

Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is AU$266 per night from 24 Dec to 25 Dec
AU$266
includes taxes & fees
24 Dec - 25 Dec
When you stay at Eaglewood Resort and Spa in Itasca, you'll be near the airport, within a 5-minute drive of Bloomingdale Park District Museum and The Oasis Water ...
Eaglewood Resort and Spa
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 24 Dec to 25 Dec
AU$181
includes taxes & fees
24 Dec - 25 Dec
Located in Schiller Park (O'Hare), Hampton Inn Chicago-O'Hare International Airport is within a 5-minute drive of Rosemont Theatre and Donald E. Stephens Convention ...
Hampton Inn Chicago-O'Hare International Airport
Chicago Getaway Hostel

Chicago Getaway Hostel

2 out of 5
616 W Arlington Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$85 per night from 2 Jan to 3 Jan
AU$85
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Chicago Getaway Hostel in Chicago (Lincoln Park), you'll be within a 5-minute drive of Wrigley Field and Michigan Avenue.
Chicago Getaway Hostel
Save an average of 15% on thousands of hotels when you're signed in
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 28 Dec to 29 Dec
AU$254
includes taxes & fees
28 Dec - 29 Dec
With a stay at Marriott Chicago O'Hare in Chicago (O'Hare), you'll be within a 5-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
Marriott Chicago O'Hare
Don't see what you're looking for?
See all available properties in Northwest Chicago
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.