Holiday Homes in Northwest Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Northwest Chicago

Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Lincoln Park Living - Suite 2!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (39)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

8.0 out of 10, Very good, (2)
"Very nice place "
The price is AU$366
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (50)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (5)
The price is AU$843
includes taxes & fees
6 Aug - 7 Aug
4BR Retreat w/ Theater, Game Room & Backyard
Charming 4 Bedroom home in the heart of Elgin
Fridge, microwave, oven, stovetop

Charming 4 Bedroom home in the heart of Elgin

9.6 out of 10, Exceptional, (34)
"Perfect for traveling as a family. Would definitely visit again "
Charming 4 Bedroom home in the heart of Elgin
Cozy 3-bedroom house in family-oriented Melrose Park.
Property grounds

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (20)
"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "
Cozy 3-bedroom house in family-oriented Melrose Park.
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Vintage Urban Retreat
Exterior detail

Vintage Urban Retreat

10.0 out of 10, Exceptional, (8)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is AU$780
includes taxes & fees
6 Aug - 7 Aug
Vintage Urban Retreat
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Terrace/patio

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (13)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (125)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, music library, video library, stereo

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (59)
"Great spot."
The price is AU$325
includes taxes & fees
18 Aug - 19 Aug
Master qtr close to nature & easy urban facilities
Lincoln Park Living - Suite 1
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (29)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1
Urban Farmhouse near O’Hare Airport
Exterior

Urban Farmhouse near O’Hare Airport

9.4 out of 10, Exceptional, (44)
"We enjoyed this old house! It was clean & furnished well. Owner very accessible & easy to work with. Would definitely stay here again!"
Urban Farmhouse near O’Hare Airport
Charming Feathers Theme Home, King Bed, 2-bedroom house in Aurora with WiFi
TV, books

Charming Feathers Theme Home, King Bed, 2-bedroom house in Aurora with WiFi

10.0 out of 10, Exceptional, (3)
"Visiting Chicago and this was a nice stay. Very quiet neighborhood. Very charming and very enjoyable."
Charming Feathers Theme Home, King Bed, 2-bedroom house in Aurora with WiFi
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Fridge, microwave, oven, stovetop

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Quaint Bungalow, near Great Lakes Naval Base
Dining

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is AU$502
includes taxes & fees
11 Aug - 12 Aug
Quaint Bungalow, near Great Lakes Naval Base
Newly Remodeled in Pistakee Bay on the Chain O' Lakes
Interior

Newly Remodeled in Pistakee Bay on the Chain O' Lakes

8.6 out of 10, Excellent, (23)
"We had a group of friends stay at this property and overall really enjoyed the relaxation of the large pool, the availability of the boat dock, and the spaciousness of the house. Great time!"
Newly Remodeled in Pistakee Bay on the Chain O' Lakes
Cheerful 3 bedroom. Feels like home.
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom. Feels like home.

3.5 star property
10.0 out of 10, Exceptional, (9)
"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"
Cheerful 3 bedroom. Feels like home.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free