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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Northwest Side Vacation Homes

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

7.8 out of 10, Good, (6)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is CA $206
CA $332 total
includes taxes & fees
Aug 25 - Aug 26
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, (52)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Fridge, microwave, oven, stovetop

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is CA $304
CA $620 total
includes taxes & fees
Sep 9 - Sep 10
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Vintage Urban Retreat
Exterior detail

Vintage Urban Retreat

10.0 out of 10, Exceptional, (9)
"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 CA $256
CA $729 total
includes taxes & fees
Aug 25 - Aug 26
Vintage Urban Retreat
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel crib

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is CA $221
CA $1,264 total
includes taxes & fees
Aug 24 - Aug 25
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (14)
"This duplex in Old Town was very tastefully refurbished and decorated. The kitchen is outfitted with the best appliances, including an electric kettle. (Note to hosts: ALWAYS provide a tea kettle of some kind and you'll get an automatic five-star rating from me!) The house is quite roomy and comfortable and the four of us settled in nicely. It's a bit of a walk to the train, but the neighborhood is nice, so you don't mind. I highly recommend."
Walk to the Beach! Theater-Coffee Bar-Games-Gym
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
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, (21)
"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.
Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

6.8 out of 10, (10)
"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
Cheerful 3 bedroom. Feels like home.
Fridge, microwave, oven, stovetop

Cheerful 3 bedroom. Feels like home.

3.5 star property
9.8 out of 10, Exceptional, (10)
"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.
Urban Farmhouse near O’Hare Airport
Exterior

Urban Farmhouse near O’Hare Airport

9.4 out of 10, Exceptional, (46)
"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
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very good, (4)
"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
New home w/view & party deck - 2nd Floor
Fridge, microwave, oven, stovetop

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (23)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

8.8 out of 10, Excellent, (6)
The price is CA $96
CA $712 total
includes taxes & fees
Aug 25 - Aug 26
4BR Retreat w/ Theater, Game Room & Backyard
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
The price is CA $148
CA $285 total
includes taxes & fees
Sep 2 - Sep 3
Master qtr close to nature & easy urban facilities
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Lobby

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is CA $151
CA $198 total
includes taxes & fees
Aug 31 - Sep 1
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Lincoln Park Living - Suite 1
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (31)
"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
Lincoln Park Living - Suite 2!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (43)
"Great Place. Super area!"
Lincoln Park Living - Suite 2!
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (90)
"Well-equipped kitchen, comfortable beds, easy parking and very clean. A perfect place to stay for our short trip to Chicago. "
SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Fridge, microwave, oven, stovetop

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

9.2 out of 10, Wonderful, (15)
"The house was very nice. Great neighborhood."
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
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 Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great experience. Close to everything. "
Peter 3-night trip
Posted 8 hours ago
Crowne Plaza Chicago West Loop by IHG