Photo by throwingsofas

Northwest Side Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Northwest Side

Smart TV, stereo
Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line

2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4)
"The place was incredible. Looks exactly as advertised. Nice neighborhood with food and coffee within walking distance. Great atmosphere! Loved my time here"
United States
Tyler S.
The price is HK$707
HK$1,716 total
includes taxes & fees
20 Nov - 21 Nov
Pine Beam Sloth Apartment next to Blue Line
2 bedrooms, iron/ironing board, WiFi, bed sheets
Warm & Inviting 2BR Apt

Warm & Inviting 2BR Apt

Hermosa
10.0 out of 10, Exceptional, (4)
"Everything was great. "
United States
John C.
The price is HK$560
HK$1,527 total
includes taxes & fees
1 Dec - 2 Dec
Warm & Inviting 2BR Apt
Fridge, microwave, oven, stovetop
1BR Homey Apt in Irving Park

1BR Homey Apt in Irving Park

Irving Park
10.0 out of 10, Exceptional, (2)
"It was wonderful and wil stay agian"
United States
Crystal P.
The price is HK$497
HK$1,319 total
includes taxes & fees
8 Dec - 9 Dec
1BR Homey Apt in Irving Park
TV
Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

2.0 star property
Irving Park
The price is HK$653
HK$2,427 total
includes taxes & fees
21 Nov - 22 Nov
Sleeps 7 • Huge Projector • Designated Workspace
Games room
Game Room • Fire-pit • Playground • Gym • Billiard

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

2.0 star property
Belmont Cragin
The price is HK$979
HK$3,955 total
includes taxes & fees
23 Nov - 24 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
Fridge, oven, stovetop, toaster
Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking

Portage Park
9.6 out of 10, Exceptional, (5)
"It was clean and well maintained unit. It’s next to grocery store and pharmacy which was very convenient. It’s not too far from downtown. I would stay again here in future if available."
United States
Jatin
The price is HK$560
HK$1,527 total
includes taxes & fees
2 Dec - 3 Dec
Homey 2BR Apt w/ Parking
Fridge, microwave, oven, stovetop
Cozy Studio in Jefferson Park

Cozy Studio in Jefferson Park

Portage Park
The price is HK$466
HK$1,205 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Studio in Jefferson Park
Interior
Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home

2.0 star property
Belmont Cragin
The price is HK$505
HK$3,943 total
includes taxes & fees
19 Nov - 20 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
Interior
Sleeps 18 • 8BR • Game Room • Gym • Theater

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

2.0 star property
Portage Park
The price is HK$1,026
HK$6,664 total
includes taxes & fees
18 Nov - 19 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
TV
2BR w/ Workspace - Coffee Bar - Near Transit

2BR w/ Workspace - Coffee Bar - Near Transit

2.0 star property
Belmont Cragin
The price is HK$754
HK$3,254 total
includes taxes & fees
23 Nov - 24 Nov
2BR w/ Workspace - Coffee Bar - Near Transit
Fridge, microwave, oven, stovetop
Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit

Portage Park
9.4 out of 10, Exceptional, (3)
"Bathroom wasn’t as clean as it should be for guests. This is a 2nd floor unit, with an extremely steep staircase, which makes getting luggage up difficult. "
United States
Adriana J.
The price is HK$497
HK$1,241 total
includes taxes & fees
3 Dec - 4 Dec
Trendy & Comfy Studio Unit
2 bedrooms, iron/ironing board, travel cot, WiFi
Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park

Irving Park
9.8 out of 10, Exceptional, (6)
"Beautiful place. The host was awesome with communication and recommendations. Will definitely stay again when we come to the city"
United States
Katie L.
The price is HK$560
HK$1,527 total
includes taxes & fees
1 Dec - 2 Dec
Chic 2BR Haven Near Irving Park
TV
New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

2.0 star property
Dunning
New Modern 3BR • Gym • Workspace • Quiet Location
Fridge, microwave, oven, stovetop
2BR Airy Apt w/ Free Parking

2BR Airy Apt w/ Free Parking

Portage Park
8.8 out of 10, Excellent, (3)
"It was a beautiful place. Lots of shared space for our two couples. Two full bedroom suites with separate bathrooms. There was garbage by the inside door when we arrived, but all else was clean and comfortable. It was a VERY humid & hot weekend, and the window a/cs just couldn't keep up, but nighttime was mostly pleasant. The owner was easy to communicate with and very fast to respond."
United States
Dona B.
The price is HK$560
HK$1,576 total
includes taxes & fees
2 Dec - 3 Dec
2BR Airy Apt w/ Free Parking
Microwave, oven, stovetop, coffee/tea maker
Bright Spaced 3BR Furnished Stay

Bright Spaced 3BR Furnished Stay

Portage Park
9.0 out of 10, Wonderful, (2)
"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 HK$606
HK$1,727 total
includes taxes & fees
1 Dec - 2 Dec
Bright Spaced 3BR Furnished Stay
Fridge, oven, stovetop, coffee/tea maker
2BR Cozy & Functional Unit

2BR Cozy & Functional Unit

Belmont Cragin
10.0 out of 10, Exceptional, (1)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
The price is HK$560
HK$1,527 total
includes taxes & fees
1 Dec - 2 Dec
2BR Cozy & Functional Unit
1 bedroom, iron/ironing board, travel cot, WiFi
Prime City Stay in a 1BR Apt

Prime City Stay in a 1BR Apt

Irving Park
9.2 out of 10, Wonderful, (11)
"Very good place over all, the area is safe from my experience. Subway is a 10 min walk from there, and a few places to go pickup a coffee or just needs. Communication with the host was good, unfortunately they are firm on their check in times. Got to airport at around 10:30 AM or earlier, so i texted the host to see if i can check in early but i had to wait because “the cleaning lady” was not done. So from 10:30 to check in time which i believe was 3pm i had to go eat and buy necessities with...
United States
Hector R.
The price is HK$497
HK$1,319 total
includes taxes & fees
1 Dec - 2 Dec
Prime City Stay in a 1BR Apt
2 bedrooms, WiFi, bed sheets
Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay

Portage Park
8.0 out of 10, Very good, (1)
"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 HK$560
HK$1,527 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 2BR Apt for a Seamless Stay
Fridge, microwave, oven, stovetop
Cozy 1-Bedroom Apartment - Sunnyside 2N

Cozy 1-Bedroom Apartment - Sunnyside 2N

Portage Park
10.0 out of 10, Exceptional, (1)
"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 HK$560
HK$1,392 total
includes taxes & fees
23 Nov - 24 Nov
Cozy 1-Bedroom Apartment - Sunnyside 2N
Iron/ironing board, travel cot, WiFi
Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!

Portage Park
The price is HK$466
HK$1,205 total
includes taxes & fees
1 Dec - 2 Dec
Comfy Studio in Portage Park- Great Value!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Northwest Side Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Clean room, spacious, free breakfast was a huge perk! "
Ashley 3-night trip
Posted 2 days ago
The Whitehall Hotel, BW Premier Collection

Find out more about Northwest Side

Search for holiday rentals in Northwest Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Northwest Side using one of the methods below:

  • View our selection of featured holiday rentals in Northwest Side
  • Use the map to find apartments and other holiday homes in the Northwest Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Northwest Side while they last

Look no further and take a look at our great range of rental properties in Northwest Side!