Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Northwest Side vacation rentals

TV, offices

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.
$176 nightly
The price is $195
May 26 - May 27
Total with taxes and fees
Cozy 1-Bedroom Apartment
Iron/ironing board, travel crib, WiFi, bed sheets

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.
$157 nightly
The price is $175
May 26 - May 27
Total with taxes and fees
Comfy Studio in Portage Park- Great Value!
Iron/ironing board, travel crib, WiFi, bed sheets

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.
$159 nightly
The price is $177
May 26 - May 27
Total with taxes and fees
Trendy & Comfy Studio Unit
2 bedrooms, iron/ironing board, travel crib, WiFi

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.
$201 nightly
The price is $222
May 19 - May 20
Total with taxes and fees
2BR Cozy & Functional Unit
TV

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.
$222 nightly
The price is $247
May 25 - May 26
Total with taxes and fees
Cozy 2BR Apt for a Seamless Stay
3 bedrooms, iron/ironing board, travel crib, WiFi

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.
$271 nightly
The price is $302
May 18 - May 19
Total with taxes and fees
Relaxing 3BR Getaway Close to Dining & Shopping
TV, offices

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
$177 nightly
The price is $197
May 26 - May 27
Total with taxes and fees
Stylish 1BR Stay in Irving Vibes
Interior

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
$223 nightly
The price is $248
May 19 - May 20
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
Interior

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.
$397 nightly
The price is $407
May 28 - May 29
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
Interior

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.
$274 nightly
The price is $324
May 25 - May 26
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
TV, offices

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.
$185 nightly
The price is $206
May 21 - May 22
Total with taxes and fees
1BR Apartment with a Warm & Welcoming Feel
Dining

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
$327 nightly
The price is $404
May 18 - May 19
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
TV, offices

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
$177 nightly
The price is $197
May 26 - May 27
Total with taxes and fees
1BR Retreat: Roomy & Well-Appointed
TV

New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location
Dunning
$310 nightly
The price is $367
May 18 - May 19
Total with taxes and fees
New Modern 3BR • Gym • Workspace • Quiet Location
TV

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.
$172 nightly
The price is $191
May 20 - May 21
Total with taxes and fees
Portage Park 1BR Retreat
TV, offices

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.
$176 nightly
The price is $195
May 20 - May 21
Total with taxes and fees
Charming 1BR in Old Irving
TV, offices

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.
$177 nightly
The price is $197
May 26 - May 27
Total with taxes and fees
Ideal & Spacious 1BR Apt
Smart TV, fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
$246 nightly
The price is $291
May 25 - May 26
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Dining

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.
$741 nightly
The price is $903
May 27 - May 28
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
TV

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.
$166 nightly
The price is $184
May 19 - May 20
Total with taxes and fees
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Room was immaculate with an incredible view and the staff was amazing!"
Casey 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Northwest Side

Everything you need to know about Northwest Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northwest Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Northwest Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $161 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Northwest Side rentals

At Expedia, we put the best Northwest Side vacation 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 vacation.

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.

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