Northwest Side Vacation Rentals

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Our top choices for Northwest Side vacation rentals

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 CA $108
CA $257 total
includes taxes & fees
May 26 - May 27
Cozy 1-Bedroom Apartment

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 CA $102
CA $235 total
includes taxes & fees
May 26 - May 27
Comfy Studio in Portage Park- Great Value!

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 CA $102
CA $235 total
includes taxes & fees
May 26 - May 27
Trendy & Comfy Studio Unit

2BR Cozy & Functional Unit

2BR Cozy & Functional Unit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"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 CA $132
CA $311 total
includes taxes & fees
May 19 - May 20
2BR Cozy & Functional Unit

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 CA $132
CA $311 total
includes taxes & fees
May 19 - May 20
Cozy 2BR Apt for a Seamless Stay

Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.4 out of 10, Exceptional, (3 reviews)
"Quick communication, great value, clean & bright."
United States
Barb S.
The price is CA $192
CA $421 total
includes taxes & fees
May 18 - May 19
Relaxing 3BR Getaway Close to Dining & Shopping

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 CA $112
CA $263 total
includes taxes & fees
May 26 - May 27
Stylish 1BR Stay in Irving Vibes

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 CA $145
CA $329 total
includes taxes & fees
May 19 - May 20
2BR Chic & Comfortable Furnished Unit

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is CA $302
CA $512 total
includes taxes & fees
May 17 - May 18
Pine Beam Sloth Apartment next to Blue Line

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 CA $123
CA $446 total
includes taxes & fees
Jun 1 - Jun 2
Sleeps 7 • Huge Projector • Designated Workspace

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 CA $126
CA $281 total
includes taxes & fees
May 25 - May 26
1BR Apartment with a Warm & Welcoming Feel

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
The price is CA $123
CA $562 total
includes taxes & fees
May 18 - May 19
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
The price is CA $112
CA $263 total
includes taxes & fees
May 26 - May 27
1BR Retreat: Roomy & Well-Appointed

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location
Dunning
The price is CA $82
CA $480 total
includes taxes & fees
May 18 - May 19
New Modern 3BR • Gym • Workspace • Quiet Location

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
8.8 out of 10, Excellent, (5 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 CA $108
CA $258 total
includes taxes & fees
May 20 - May 21
Portage Park 1BR Retreat

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 CA $112
CA $265 total
includes taxes & fees
May 20 - May 21
Charming 1BR in Old Irving

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 CA $112
CA $263 total
includes taxes & fees
May 26 - May 27
Ideal & Spacious 1BR Apt

Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
The price is CA $89
CA $399 total
includes taxes & fees
May 27 - May 28
Studio Near Wrigley • Sleeps 4 • Games + Fireplace

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is CA $164
CA $1,184 total
includes taxes & fees
May 18 - May 19
Sleeps 18 • 8BR • Game Room • Gym • Theater

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 CA $102
CA $249 total
includes taxes & fees
May 19 - May 20
1BR Gem by Shops & Dining
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.