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

Northwest Side Vacation Rentals

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Check prices for these dates

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

Our top choices for Northwest Side vacation 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 ￥40,738
￥46,636 total
includes taxes & fees
Nov 9 - Nov 10
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, (59 reviews)
"Location is perfect"
United States
Mary
The price is ￥28,264
￥42,988 total
includes taxes & fees
Nov 1 - Nov 2
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, (538 reviews)
"Beautiful property, great amenities."
United States
Erik
The price is ￥43,699
￥55,194 total
includes taxes & fees
Nov 1 - Nov 2
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, (1,363 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥26,401
￥30,992 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥30,265
￥52,183 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥24,316
￥28,543 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥25,452
￥46,671 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥38,212
￥74,976 total
includes taxes & fees
Oct 14 - Oct 15
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)
The price is ￥17,180
￥37,202 total
includes taxes & fees
Oct 28 - Oct 29
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

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

8/10 Good
"The staff was lovely as was the room. The lobby area is in need of a serious renovation, but otherwise, it’s a great property."
Marjorie 2-night trip
Posted 4 hours ago
Sports Illustrated Resorts Chicago

Find out more about Northwest Side

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