A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Northwest Side vacation rentals

TV

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

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Great host any concerns that I had were addressed and handled!"
United States
Keana
$477 nightly
The price is $580
Jul 14 - Jul 15
Total with taxes and fees
4BR Retreat w/ Theater, Arcade, Gym and Firepit
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.
$307 nightly
The price is $379
Jul 16 - Jul 17
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, (4 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$270 nightly
The price is $319
Aug 11 - Aug 12
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
Fridge, microwave, oven, stovetop

3BR Modern Apt • Gym • Workspace • Quiet Location

3BR Modern Apt • Gym • Workspace • Quiet Location
Dunning
3BR Modern Apt • Gym • Workspace • Quiet Location
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.
$237 nightly
The price is $280
Jul 22 - Jul 23
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
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.
$650 nightly
The price is $728
Jul 15 - Jul 16
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15
Dining

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (2 reviews)
"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.
$716 nightly
The price is $872
Jul 14 - Jul 15
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
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, (7 reviews)
"The place was clean, cozy and exactly as described. Very responsive host and would definitely stay again. "
United States
Carlos J B.
$345 nightly
The price is $356
Jul 16 - Jul 17
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
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.
$436 nightly
The price is $515
Aug 11 - Aug 12
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
Iron/ironing board, travel crib, WiFi, bed sheets

Stylish 3BR Apt | Gym and Workspace | Near O’Hare

Stylish 3BR Apt | Gym and Workspace | Near O’Hare
Dunning
$353 nightly
The price is $418
Jul 19 - Jul 20
Total with taxes and fees
Stylish 3BR Apt | Gym and Workspace | Near O’Hare
Interior

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
10.0 out of 10, Exceptional, (2 reviews)
"G"
United States
Aleah
$260 nightly
The price is $307
Jul 20 - Jul 21
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
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
$317 nightly
The price is $391
Jul 27 - Jul 28
Total with taxes and fees
2BR Traveler's Favorite • Modern and Clean
1 bedroom, iron/ironing board, travel crib, free WiFi

Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at this property! After our previous rental cancelled at the last minute, we found this gem and couldn’t have been happier. Communication was clear, check-in was easy, and the property was clean and comfortable. Thanks for a great stay!"
United States
Emily G.
$237 nightly
The price is $280
Jul 22 - Jul 23
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
TV

2BR w/ Workspace - Coffee Bar - Near Transit

2BR w/ Workspace - Coffee Bar - Near Transit
Belmont Cragin
$323 nightly
The price is $399
Aug 4 - Aug 5
Total with taxes and fees
2BR w/ Workspace - Coffee Bar - Near Transit
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.
$245 nightly
The price is $290
Aug 5 - Aug 6
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace
7 bedrooms, iron/ironing board, travel crib, WiFi

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
$1,105 nightly
The price is $1,306
Aug 10 - Aug 11
Total with taxes and fees
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,210 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
$208 nightly
The price is $244
Aug 9 - Aug 10
Total with taxes and fees
Sentral Michigan Avenue
Living area

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
$230 nightly
The price is $263
Jul 26 - Jul 27
Total with taxes and fees
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
$618 nightly
The price is $763
Jul 16 - Jul 17
Total with taxes and fees
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (84 reviews)
"Wonderful hosts…very kind and communicative. Awesome area… highly recommended!"
United States
Andrew C.
$154 nightly
The price is $189
Jul 27 - Jul 28
Total with taxes and fees
Cozy studio in Andersonville Chicago
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

Hyatt Regency Chicago

Hyatt Regency Chicago

8/10 Good
"Hotel and stay were great. Check in was a long line check out was even longer. Online it says you can check out at a kiosk but there weren’t any"
Kristina 1-night trip
Posted 1 hour ago
Hyatt Regency 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 $219 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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