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Northwest Side Vacation Rentals

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Our top choices for Northwest Side vacation rentals

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
$814 nightly
The price is $990
Jul 15 - Jul 16
Total with taxes and fees
4BR Retreat w/ Theater, Arcade, Gym and Firepit

3BR Modern Apt • Gym • Workspace • Quiet Location

3BR Modern Apt • Gym • Workspace • Quiet Location
Dunning
3BR Modern Apt • Gym • Workspace • Quiet Location

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"My group and I traveled to town this weekend for a music festival and had the opportunity to stay at this place and had a great time. Communication with the host was very prompt when we had any questions which I appreciate a lot. Also, the place was clean and spacious for our group and easy to come in and out. Would recommend this place to others looking for a place to stay in town."
United States
Marcos B.
$330 nightly
The price is $408
Jul 6 - Jul 7
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$232 nightly
The price is $274
Jul 13 - Jul 14
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace

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.
$243 nightly
The price is $287
Jul 1 - Jul 2
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Property was the perfect size for our group. Neighborhood was quiet. Street parking was available directly in front of the house. Great experience!!!!"
United States
Justin C.
$459 nightly
The price is $543
Jul 9 - Jul 10
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard

2BR w/ Workspace - Coffee Bar - Near Transit

2BR w/ Workspace - Coffee Bar - Near Transit
Belmont Cragin
$322 nightly
The price is $398
Jul 1 - Jul 2
Total with taxes and fees
2BR w/ Workspace - Coffee Bar - Near Transit

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
$268 nightly
The price is $317
Jul 20 - Jul 21
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7

Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (1 review)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
$257 nightly
The price is $304
Jul 28 - Jul 29
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (2 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
$754 nightly
The price is $845
Jul 8 - Jul 9
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15

2BR Traveler's Favorite • Modern and Clean

2BR Traveler's Favorite • Modern and Clean
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"It’s a really nice and cozy place to stay at but the upstairs guest could’ve little disturbing at times."
United States
nishaa
$358 nightly
The price is $442
Jul 27 - Jul 28
Total with taxes and fees
2BR Traveler's Favorite • Modern and Clean

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
$173 nightly
The price is $203
Jul 5 - Jul 6
Total with taxes and fees
Sentral Michigan Avenue

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (148 reviews)
"Perfect place to stay!"
United States
Anton
$212 nightly
The price is $243
Jul 1 - Jul 2
Total with taxes and fees
The Gem Museum Suites

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay"
United States
Anonymous traveler
$115 nightly
The price is $127
Jul 1 - Jul 2
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$258 nightly
The price is $296
Jul 27 - Jul 28
Total with taxes and fees
The Oak Park Loft

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (84 reviews)
"nice little place! quiet area "
United States
Nayeli A.
$202 nightly
The price is $214
Jul 5 - Jul 6
Total with taxes and fees
Master qtr close to nature & easy urban facilities

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Great place! "
United States
Isabella T.
$237 nightly
The price is $254
Jul 4 - Jul 5
Total with taxes and fees
Just remodeled apartment close to airport and mall

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
9.8 out of 10, Exceptional, (39 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.2 out of 10, Wonderful, (7 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$299 nightly
The price is $351
Jul 6 - Jul 7
Total with taxes and fees
Level Chicago – Old Town
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 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 $189 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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