Northwest Side Vacation Rentals

Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Northwest Side vacation rentals

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.
$155 nightly
The price is $173
May 26 - May 27
Total with taxes and fees
Comfy Studio in Portage Park- Great Value!
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.
$172 nightly
The price is $191
May 26 - May 27
Total with taxes and fees
Cozy 1-Bedroom Apartment
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.
$145 nightly
The price is $161
May 26 - May 27
Total with taxes and fees
Trendy & Comfy Studio Unit
2 bedrooms, iron/ironing board, travel crib, WiFi

Cozy Cragin 2BR Apartment Near Logan Square

Cozy Cragin 2BR Apartment Near Logan Square
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.
$220 nightly
The price is $245
May 26 - May 27
Total with taxes and fees
Cozy Cragin 2BR Apartment Near Logan Square
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
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
$178 nightly
The price is $198
May 26 - May 27
Total with taxes and fees
Stylish 1BR Stay in Irving Vibes
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.
$279 nightly
The price is $312
May 26 - May 27
Total with taxes and fees
Relaxing 3BR Getaway Close to Dining & Shopping
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.
$186 nightly
The price is $207
May 25 - May 26
Total with taxes and fees
1BR Apartment with a Warm & Welcoming Feel
TV

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.
$170 nightly
The price is $188
May 20 - May 21
Total with taxes and fees
Portage Park 1BR Retreat
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
$205 nightly
The price is $227
May 20 - May 21
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
Dining

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
$324 nightly
The price is $400
May 20 - May 21
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
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.
$240 nightly
The price is $284
May 25 - May 26
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
TV, offices

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
$179 nightly
The price is $199
May 26 - May 27
Total with taxes and fees
1BR Retreat: Roomy & Well-Appointed
Fridge, microwave, oven, stovetop

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
$475 nightly
The price is $562
Jun 9 - Jun 10
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
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.
$178 nightly
The price is $198
May 26 - May 27
Total with taxes and fees
Ideal & Spacious 1BR Apt
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
1 bedroom, iron/ironing board, WiFi, bed sheets

Sleeps 4 • New Modern 1BR • Private Workspace

Sleeps 4 • New Modern 1BR • Private Workspace
Irving Park
10.0 out of 10, Exceptional, (1 review)
"Really nice apartment with ample street parking. Depending on what time you get there it might be harder to find a spot but we got there around 8pm and found a spot very close to the apartment. Host was very responsive, only thing is i wish they would have sent the check in codes to my phone as a text rather than as a message through the app since it didn’t load all the way and it took some time to receive it. Spacious, Great amenities, perfect for multiple guests. Walls are a bit thin as I...
United States
Mia S.
$244 nightly
The price is $289
May 20 - May 21
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace
Interior

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
$697 nightly
The price is $781
May 20 - May 21
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15
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.
$171 nightly
The price is $190
May 25 - May 26
Total with taxes and fees
1BR Gem by Shops & Dining
TV

Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
10.0 out of 10, Exceptional, (1 review)
"Very clean and pet-friendly property—everything was neat, and the host was super responsive.The only drawback is that some furniture feels worn, so you need to be careful (the curtain in my mom’s room had loose pieces).Overall, we had a great stay!Thanks.Taisa."
United States
Taisa C.
$222 nightly
The price is $247
May 26 - May 27
Total with taxes and fees
Cozy 2BR Apartment w/ Washer & Dryer
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

6/10 Okay
"Ambassador Gold Coast Hotel was alright at best. Charging a $150 deposit for the room was excessive and disappointing. The staff was okay, but most of them seemed to have an attitude, which made the experience less enjoyable. "
Jaylen 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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.

Explore a world of travel with Expedia