A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Northwest Side holiday rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is HK$1,560
HK$1,786 total
includes taxes & fees
31 Oct - 1 Nov
The Gem Museum Suites
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (58 reviews)
"Location is perfect"
United States
Mary
The price is HK$1,405
HK$2,137 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (537 reviews)
"Beautiful property, great amenities."
United States
Erik
The price is HK$1,781
HK$2,285 total
includes taxes & fees
4 Nov - 5 Nov
Level Chicago – Old Town
A modern building with the name 'SENIORAL' prominently displayed on the facade.

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,362 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,438
HK$1,688 total
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue
Terrace/patio

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,504
HK$2,593 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,165
HK$1,368 total
includes taxes & fees
3 Nov - 4 Nov
Wrigleyville Suites
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is HK$1,265
HK$2,320 total
includes taxes & fees
27 Oct - 28 Oct
Historic Oak Park Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is HK$1,899
HK$3,726 total
includes taxes & fees
14 Oct - 15 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A building with a white exterior and a tree with white blossoms in front.

9. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

10. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$854
HK$1,849 total
includes taxes & fees
28 Oct - 29 Oct
The Oak Park Loft
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Our stay at the Hilton Chicago was excellent.The rooms were clean,staff very professional,and food was excellent."
Gertrude S 4-night trip
Posted 2 hours ago
Hilton Chicago

Find out more about Northwest Side

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