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

Northwest Side Holiday Rentals

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Our top choices for Northwest Side holiday rentals

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.8 out of 10, Good, (58 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NZ$308
includes taxes & fees
29 Sept - 30 Sept
Wrigleyville Suites

2. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (271 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is NZ$368
includes taxes & fees
28 Sept - 29 Sept
The Gem Museum Suites

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,343 reviews)
"Great venue"
United States
Arthur Noel
The price is NZ$415
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue

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 NZ$646
includes taxes & fees
6 Oct - 7 Oct
At Home in Oak Park

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (41 reviews)
"Great location and room"
United States
Miriam
The price is NZ$509
includes taxes & fees
1 Oct - 2 Oct
Kasa Lake Shore Chicago

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 NZ$638
includes taxes & fees
14 Oct - 15 Oct
Historic Oak Park Home

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (530 reviews)
"Location and facility was very nice"
United States
Brian
The price is NZ$670
includes taxes & fees
26 Oct - 27 Oct
Level Chicago – Old Town

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 NZ$838
includes taxes & fees
28 Sept - 29 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line

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 NZ$555
includes taxes & fees
13 Oct - 14 Oct
The Oak Park Loft

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 NZ$682
includes taxes & fees
21 Oct - 22 Oct
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

Find out more about Northwest Side

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Northwest Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Northwest Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Northwest Side. Seeing all the best attractions is bound to make you fall in love with Northwest Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Northwest Side short-term rentals, that won’t be hard to do.

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