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Northwest Side Holiday Rentals

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Holiday Rentals in Northwest Side

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is AU$1,382
includes taxes & fees
30 Sept - 1 Oct
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is AU$300
includes taxes & fees
10 Sept - 11 Sept
Prime City Stay in a 1BR Apt

Central Haven Escape: Stylish 3BR With Free Parking

6.8 out of 10, (6)
"The overall experience was surprisingly great. We were a little worried after reading some bad reviews because of the house smelling like smoke. It didn’t. In fact, it smelled super clean and fresh. It is a cute little, older, clean 3 bedroom apartment above a building in a downtown neighborhood. So cute!"
Central Haven Escape: Stylish 3BR With Free Parking

Huge Projector and Designated Workspace - Near Wrigley!

10.0 out of 10, Exceptional, (1)
"Nice and clean, location is perfect. Easy street parking and walkable to public transportation. Check in was easy. "
The price is AU$463
includes taxes & fees
8 Sept - 9 Sept
Huge Projector and Designated Workspace - Near Wrigley!

2BR w/ Workspace + Coffee Bar • Near Transit

6.0 out of 10, (2)
"Newly refurbished apartment space was lovely! Management company was easily accessible and was very helpful. The heat of the summer kept the space a little warm (has two AC window units). "
The price is AU$650
includes taxes & fees
31 Aug - 1 Sept
2BR w/ Workspace + Coffee Bar • Near Transit

2BR Traveler's Favorite, Modern and Clean

10.0 out of 10, Exceptional, (1)
"The place was really nice and clean, an excellent stay that ill consider again my next trip to chicago"
The price is AU$553
includes taxes & fees
2 Sept - 3 Sept
2BR Traveler's Favorite, Modern and Clean

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

3BR Oasis, Gym, Workspace, Quiet Location

2.0 star property
10.0 out of 10, Exceptional, (1)
"Convenient, beautiful, and clean stay! We would stay again"
3BR Oasis, Gym, Workspace, Quiet Location

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (898)
"great food spots all around and beautiful sites to see "
The price is AU$287
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (487)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (345)
"A lot of good food options walkable distance. "
The price is AU$435
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (350)
"Great stay!"
The price is AU$267
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (635)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is AU$267
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (193)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (208)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is AU$304
includes taxes & fees
14 Sept - 15 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (86)
"Super nice hotel and staff "
The price is AU$350
includes taxes & fees
2 Sept - 3 Sept
The Gem Museum Suites

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (334)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is AU$267
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is AU$276
includes taxes & fees
1 Sept - 2 Sept
Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is AU$304
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
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 favourite 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 depend 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 AU$267 per night. Entering your travel dates in the search wizard might find you 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.