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Northwest Side Holiday Rentals

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Holiday Rentals in Northwest Side

2BR Traveler`s Favorite • Modern and Clean

10.0 out of 10, Exceptional, (2)
"Clean, comfortable, and secure"
The price is NZ$616
includes taxes & fees
7 Oct - 8 Oct
2BR Traveler`s Favorite • Modern and Clean

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (10)
"Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit."
The price is NZ$312
includes taxes & fees
1 Oct - 2 Oct
Prime City Stay in a 1BR Apt

Sleeps 4 • Stylish Stay with Workspace

9.8 out of 10, Exceptional, (7)
The price is NZ$650
includes taxes & fees
10 Oct - 11 Oct
Sleeps 4 • Stylish Stay with Workspace

Sleeps 18 • 8BR • Game Room • Gym • Theater

5.4 out of 10, (3)
"Great space for large groups. Park across the street is a great "feature"."
The price is NZ$1,505
includes taxes & fees
29 Sept - 30 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater

2BR Fitness Pad • Private Gym • Sleeps 7

9.6 out of 10, Exceptional, (5)
"I really liked how quiet and nice it was around the area "
The price is NZ$511
includes taxes & fees
6 Oct - 7 Oct
2BR Fitness Pad • Private Gym • Sleeps 7

Sleeps 7 • Huge Projector • Designated Workspace

6.0 out of 10, (4)
"Overall the property was fine. The remote for the garage door was missing and the dryer was not working properly. The dryer created the bigger issue needing to wash towels so everyone could shower daily. "
The price is NZ$530
includes taxes & fees
13 Oct - 14 Oct
Sleeps 7 • Huge Projector • Designated Workspace

New Modern 3BR • Gym • Workspace • Quiet Location

2.0 star property
8.0 out of 10, Very good, (2)
"Great time, clean and lovely place in a quiet area!"
New Modern 3BR • Gym • Workspace • Quiet Location

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (936)
"The staff was extremely helpful and the rooms are clean with a beautiful view of downtown and the lake. I will definitely stay here again. "
The price is NZ$447
includes taxes & fees
5 Oct - 6 Oct
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (535)
"Very great place to stay!"
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (358)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (371)
"Great stay!"
The price is NZ$275
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (231)
"Great location and lovely amenities. "
The price is NZ$379
includes taxes & fees
18 Oct - 19 Oct
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (354)
"It was a really nice and secure property. "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (665)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is NZ$405
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (205)
"This place was perfect "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (51)
"Place was in a great location close to good restaurants "
The price is NZ$344
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
Kasa River North Chicago

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is NZ$436
includes taxes & fees
29 Sept - 30 Sept
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is NZ$250
includes taxes & fees
1 Oct - 2 Oct
Wrigleyville Suites

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (180)
"Great location!!!"
The price is NZ$364
includes taxes & fees
1 Oct - 2 Oct
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
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

Find out more about Northwest Side

Everything you need to know about Northwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Northwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Northwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Northwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Northwest Side holiday rentals we have selected for you start as low as NZ$250 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Northwest Side rentals

At Expedia, we put the best Northwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Northwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Northwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Northwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.