Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Northwest Side

Pool
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Apartment in Portage Park

10.0 out of 10, Exceptional, (112)
"Very nice place to stay. Host was very friendly and helpful."
United States
JoEllen P.
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Smart TV
Central Haven Escape: Stylish 3BR With Free Parking

Apartment in Irving Park

6.0 out of 10, (7)
"Very nice place and nice host "
United States
Maryo K.
Central Haven Escape: Stylish 3BR With Free Parking
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥15,825
￥23,185 total
includes taxes & fees
Dec 10 - Dec 11
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (625)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (384)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

Aparthotel in Near West Side

4.0 star property
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Aparthotel in Lakeview

2.0 star property
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ￥18,842
￥22,120 total
includes taxes & fees
Nov 24 - Nov 25
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is ￥26,266
￥30,069 total
includes taxes & fees
Nov 30 - Dec 1
The Gem Museum Suites
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is ￥45,935
￥53,924 total
includes taxes & fees
Nov 23 - Nov 24
Chicago luxury home suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Apartment in Lakeview

9.2 out of 10, Wonderful, (35)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
United States
Camron K.
The price is ￥8,637
￥24,986 total
includes taxes & fees
Nov 30 - Dec 1
Clean & Equipped 1BR Apt
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is ￥38,125
￥60,979 total
includes taxes & fees
Dec 2 - Dec 3
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Apartment in Lakeview

9.4 out of 10, Exceptional, (26)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is ￥9,422
￥28,457 total
includes taxes & fees
Dec 9 - Dec 10
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥8,637
￥24,986 total
includes taxes & fees
Nov 30 - Dec 1
Stylish 1BR in West Loop
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Apartment in Near West Side

10.0 out of 10, Exceptional, (268)
"Lovely place! Very clean and has all of the amenities necessary for a good stay. Lots of fresh towels, a fully stocked kitchen and the location is excellent. "
United States
Angela C.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
Remodeled West Loop Apartment Near United Center

Apartment in Near West Side

9.0 out of 10, Wonderful, (56)
"This apartment is very close to downtown with easy parking right outside! The unit is very well maintained with spacious rooms and amenities! The host has thought of everything to make it feel like your own home! Would love to come back and stay here again!"
United States
kiran
Remodeled West Loop Apartment Near United Center
Interior
Art Villa

Aparthotel in West Town

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is ￥59,252
￥126,024 total
includes taxes & fees
Nov 30 - Dec 1
Art Villa
2 bedrooms, iron/ironing board, travel crib, WiFi
Charming 2BR in Vibrant Lakeview

Apartment in Lakeview

9.0 out of 10, Wonderful, (30)
"Great stay. Place was spic and span on arrival and host very easy to communicate with. "
United States
Lukas H O.
The price is ￥9,736
￥28,826 total
includes taxes & fees
Nov 30 - Dec 1
Charming 2BR in Vibrant Lakeview
Fridge, microwave, oven, stovetop
LakeHouse

Vacation Home in South Shore

9.4 out of 10, Exceptional, (24)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
United States
Isaiah P.
LakeHouse
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Very Nice Hotel. Convenient location to Magnificent Mile shops. Clean rooms, breakfast buffet was great! "
Vanessa 1-night trip
Posted 8 hours ago
Hotel Riu Plaza Chicago

Find out more about Northwest Side

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