Holiday Homes in Northwest Chicago

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Northwest Chicago

Clarendon Hills Top Floor
Enjoy cooking in this well-equipped kitchen with a stainless steel range hood and a central sink.

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!
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and dishwasher.

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (38)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (48)
"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
Enjoy meals in this dining area with a wooden table, white chairs, and a large mirror.

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (4)
"Great place"
The price is NZ$1,042
includes taxes & fees
20 Aug - 21 Aug
4BR Retreat w/ Theater, Game Room & Backyard
Charming 4 Bedroom home in the heart of Elgin
Enjoy meals in this kitchen with a window and dining area nearby.

Charming 4 Bedroom home in the heart of Elgin

9.6 out of 10, Exceptional, (30)
"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.
Stunning single-family home with a backyard surrounded by mature trees and a well-manicured lawn.

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

10.0 out of 10, Exceptional, (16)
"Clean and in a nice neighborhood "
Cozy 3-bedroom house in family-oriented Melrose Park.
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Enjoy cooking in this well-equipped kitchen with a large island, dishwasher, oven, microwave, and coffee maker.

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

10.0 out of 10, Exceptional, (86)
"Easy to get to and very clean. Also check in and out was easy as well. "
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square
Relax by the fire pit in this serene outdoor space, surrounded by comfortable seating and lush greenery.

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

10.0 out of 10, Exceptional, (12)
"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, (124)
"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
Relax in this spacious living room with a large L-shaped sofa, smaller sofa, and chaise lounge.

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

9.0 out of 10, Wonderful, (30)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Master qtr close to nature & easy urban facilities
Stunning home with a covered porch, large windows, and beautifully landscaped yard.

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (58)
"Great spot."
The price is NZ$333
includes taxes & fees
28 July - 29 July
Master qtr close to nature & easy urban facilities
Lincoln Park Living - Suite 1
Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, sink, and coffee maker.

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (29)
"Great location in a beautiful part of town. Walk to Wrigley. Place was great for 2 families to hang out. "
Lincoln Park Living - Suite 1
Urban Farmhouse near O’Hare Airport
Stroll up to this charming two-story home with a welcoming front porch and central chimney.

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
Relax in this stylish living room with a grey sofa, dark blue armchair, and large flat-screen TV.

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

10.0 out of 10, Exceptional, (2)
"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!!
Enjoy cooking in this well-equipped kitchen with a large window and stainless steel appliances.

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
Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is NZ$508
includes taxes & fees
27 July - 28 July
Quaint Bungalow, near Great Lakes Naval Base
Cheerful 3 bedroom. Feels like home.
Enjoy cooking in this well-equipped kitchen with oven, microwave, and 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.
Newly Remodeled in Pistakee Bay on the Chain O' Lakes
Relax in this stylish living area with a round dining table, comfortable sofa, and flat-screen TV.

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
Stylish 3bd w/ backyard patio mins from Downtown!
Enjoy cooking in this well-equipped kitchen with an island and stainless steel appliances.

Stylish 3bd w/ backyard patio mins from Downtown!

2.0 star property
8.8 out of 10, Excellent, (3)
"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "
Stylish 3bd w/ backyard patio mins from Downtown!
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
Enjoy cooking in this well-equipped kitchen with a stainless steel stove, microwave, and sink with a dish rack.

Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie

7.4 out of 10, Good, (3)
"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
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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Top Northwest Chicago Hotel Reviews

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Overall a great hotel for my needs. Had my flight come in late at night and next segment early in am."
Evelyne 1-night trip
Posted 1 day ago
Hilton Chicago O'Hare Airport