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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Northwest Side vacation rentals

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.8 out of 10, Good, (61 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NT$4,719
NT$5,540 total
includes taxes & fees
Sep 30 - Oct 1
Wrigleyville Suites
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

2. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (272 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is NT$5,673
NT$6,494 total
includes taxes & fees
Oct 29 - Oct 30
The Gem Museum Suites
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,345 reviews)
"Great venue"
United States
Arthur Noel
The price is NT$5,568
NT$7,469 total
includes taxes & fees
Oct 26 - Oct 27
Sentral Michigan Avenue
Terrace/patio

4. 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 NT$7,080
NT$11,634 total
includes taxes & fees
Oct 6 - Oct 7
At Home in Oak Park
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (47 reviews)
"Location is perfect"
United States
Mary
The price is NT$6,578
NT$9,710 total
includes taxes & fees
Sep 30 - Oct 1
Kasa Lake Shore Chicago
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

6. 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 NT$5,123
NT$9,393 total
includes taxes & fees
Oct 27 - Oct 28
Historic Oak Park Home
A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (532 reviews)
"Location and facility was very nice"
United States
Brian
The price is NT$9,546
NT$11,990 total
includes taxes & fees
Oct 29 - Oct 30
Level Chicago – Old Town
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 NT$7,685
NT$15,078 total
includes taxes & fees
Sep 30 - Oct 1
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,644
NT$9,990 total
includes taxes & fees
Oct 13 - Oct 14
The Oak Park Loft
A building with a white exterior and a tree with white blossoms in front.

10. 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
The price is NT$7,642
NT$12,277 total
includes taxes & fees
Oct 21 - Oct 22
Historic Oak Park Residence
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

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Excelente relación precio calidad"
Andres 1-night trip
Posted less than an hour ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Find out more about Northwest Side

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