Northwest Side Holiday Rentals

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Our top choices for Northwest Side holiday rentals

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
The price is AU$276
includes taxes & fees
9 June - 10 June
Trendy & Comfy Studio Unit

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (1 review)
"Great location and easy on street parking. "
United States
Lori A.
The price is AU$449
includes taxes & fees
17 June - 18 June
Sleeps 7 • Huge Projector • Designated Workspace

Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "
United States
Sarah M.
The price is AU$330
includes taxes & fees
24 June - 25 June
Cozy 1-Bedroom Apartment

Cozy 2BR with King Beds + Full Kitchen

Cozy 2BR with King Beds + Full Kitchen
Portage Park
2.0 out of 10, (1 review)
The price is AU$293
includes taxes & fees
3 June - 4 June
Cozy 2BR with King Beds + Full Kitchen

Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly, helpful, and communicative. The apartment was clean and quiet. "
United States
Clifton C.
The price is AU$243
includes taxes & fees
3 June - 4 June
Comfy Studio in Portage Park- Great Value!

Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
The price is AU$439
includes taxes & fees
30 June - 1 July
Private Workspace • Sleeps4 • Modern Stylish Stay

1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
The price is AU$298
includes taxes & fees
16 June - 17 June
1BR 1BA Windy City Hideout

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Great property in a great neighborhood. Very comfortable during our stay. The apartment covered all of our needs during our stay."
United States
BETELHEM M.
The price is AU$569
includes taxes & fees
4 June - 5 June
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
9.0 out of 10, Wonderful, (6 reviews)
"Great stay. Very good instructions along with video for entry. Clean and comfortable! Enjoyed our stay. Great Colombian coffee shop right downstairs to the right of the entrance."
United States
Ann F.
The price is AU$275
includes taxes & fees
8 June - 9 June
Portage Park 1BR Retreat

1BR Gem by Shops & Dining

1BR Gem by Shops & Dining
Portage Park
6.0 out of 10, (2 reviews)
"The location was great for us as we were visiting family in the area. Everything worked well for us although more loghting in the bathroom would be a helpful."
United States
Matt E.
The price is AU$313
includes taxes & fees
11 June - 12 June
1BR Gem by Shops & Dining

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
The price is AU$244
includes taxes & fees
8 June - 9 June
1BR Retreat: Roomy & Well-Appointed

Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.4 out of 10, Exceptional, (3 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is AU$375
includes taxes & fees
9 June - 10 June
Relaxing 3BR Getaway Close to Dining & Shopping

Cozy Studio in Jefferson Park

Cozy Studio in Jefferson Park
Portage Park
2.0 out of 10, (1 review)
"There was no heat so I left after an hour. The host said I should wait for the radiators to cycle in to heat up. There were 3 radiators and two of them were ice cold. The one that did get a little warm was hissing steam and leaking ion the floor. I’m 71 years old and wasn’t planning on a camping trip. So I left and found another place. I will insist on nothing but a full refund and in fact should be compensated for the inconvenience and hardship. "
United States
Victoria A.
The price is AU$273
includes taxes & fees
9 June - 10 June
Cozy Studio in Jefferson Park

1BR Apartment with a Warm & Welcoming Feel

1BR Apartment with a Warm & Welcoming Feel
Irving Park
9.0 out of 10, Wonderful, (4 reviews)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is AU$288
includes taxes & fees
4 June - 5 June
1BR Apartment with a Warm & Welcoming Feel

Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay
Portage Park
8.0 out of 10, Very good, (1 review)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
United States
Michael P.
The price is AU$288
includes taxes & fees
3 June - 4 June
Cozy 2BR Apt for a Seamless Stay

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
9.0 out of 10, Wonderful, (7 reviews)
"Comfortable beds, great location"
United States
Jason
The price is AU$362
includes taxes & fees
9 June - 10 June
2BR Chic & Comfortable Furnished Unit

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
8.4 out of 10, Very good, (5 reviews)
"Great place to stay Comfy bed and setting"
United States
Steven
The price is AU$283
includes taxes & fees
8 June - 9 June
Stylish 1BR Stay in Irving Vibes

Ideal & Spacious 1BR Apt

Ideal & Spacious 1BR Apt
Irving Park
8.0 out of 10, Very good, (2 reviews)
"Excellent location. Clean. Quiet building. Host was incredibly responsive. There was a blizzard during our stay and the host graciously accomodated our request to extend our visit!"
United States
Jackie F.
The price is AU$260
includes taxes & fees
7 June - 8 June
Ideal & Spacious 1BR Apt

Charming 1BR in Old Irving

Charming 1BR in Old Irving
Irving Park
7.0 out of 10, Good, (2 reviews)
"Despite how cute the apartment was, the radiators are not on a thermostat in the unit and the house was very hot. Whatever timer they used kicked on around 4 am and the radiators all released steam for 2-3 hours straight. It was so loud they left earplugs by the bed. The couch in the living room is so bad it should be replaced ASAP. They need one table or dresser in the bedroom for clothes. There are a good amount of hangers in the closet, but no drawers or shelves anymore so you can't unpack a...
United States
David C.
The price is AU$330
includes taxes & fees
12 June - 13 June
Charming 1BR in Old Irving

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
The price is AU$704
includes taxes & fees
4 June - 5 June
Game Room • Fire-pit • Playground • Gym • Billiard
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

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$219 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.