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Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Northwest Side vacation rentals

TV

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
Interior

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
Fridge, microwave, oven, stovetop

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.
$460 nightly
The price is $544
Jul 9 - Jul 10
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
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.
$243 nightly
The price is $287
Jul 1 - Jul 2
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace
Dining

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.
$332 nightly
The price is $410
Jul 6 - Jul 7
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
7 bedrooms, desk, iron/ironing board, travel crib

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.
$665 nightly
The price is $745
Jul 8 - Jul 9
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15
Game room

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

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
$813 nightly
The price is $989
Jul 13 - Jul 14
Total with taxes and fees
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Interior

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
TV

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
Fridge, microwave, oven, stovetop

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
Indoor pool

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
$186 nightly
The price is $218
Jul 1 - Jul 2
Total with taxes and fees
Sentral Michigan Avenue
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"The property was clean and the location was great."
United States
Steven C.
$521 nightly
The price is $643
Jul 8 - Jul 9
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (84 reviews)
"Great location for a short trip "
United States
Eric W.
$296 nightly
The price is $365
Jul 1 - Jul 2
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior

2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
$278 nightly
The price is $337
Jul 3 - Jul 4
Total with taxes and fees
2MI to Obama Center - Pet-Friendly near UOC!
Full-size fridge, microwave, oven, stovetop

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 8 - Jul 9
Total with taxes and fees
Level Chicago – Old Town
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
$158 nightly
The price is $187
Jul 1 - Jul 2
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$170 nightly
The price is $201
Jul 1 - Jul 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
Fridge, microwave, oven, stovetop

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
$451 nightly
The price is $521
Jul 9 - Jul 10
Total with taxes and fees
River North Rooftop With In and Out Parking 5
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
$255 nightly
The price is $300
Jul 5 - Jul 6
Total with taxes and fees
Kasa River North Chicago
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

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
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"This hotel was perfect for 4 days in Chicago to explore. Walking distance to many shops, restaurants and attractions. The included breakfast was an added bonus and the rooftop bar was great! Staff here were always so pleasant and helpful being quick to take your bags, press the button for the elevator and helping with checking in quickly and using the express checkout; never did we have to wait or ask for assistance. The room was perfect (clean, spacious) and had everything we needed. Would definitely stay again and recommend it to others."
Cheryl 4-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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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