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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Northwest Side vacation rentals

A hallway with wooden flooring, a mirror, a potted plant, and a wooden cabinet with drawers.

1. Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (8 reviews)
"The place was clean, cozy and exactly as described. Very responsive host and would definitely stay again. "
United States
Carlos J B.
$311 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.4 out of 10, Exceptional, (6 reviews)
"Room was nice and in a safe location."
United States
Jacob
$329 nightly
The price is $406
Sep 8 - Sep 9
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

3. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (4 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
$450 nightly
The price is $547
Aug 30 - Aug 31
Total with taxes and fees
4BR Retreat w/ Theater, Arcade, Gym and Firepit
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (6 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.
$725 nightly
The price is $884
Sep 8 - Sep 9
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
$380 nightly
The price is $449
Aug 31 - Sep 1
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

6. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$273 nightly
The price is $323
Sep 15 - Sep 16
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace

7. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
$630 nightly
The price is $706
Sep 1 - Sep 2
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15

8. Private Gym and Workspace • 3BR in Quiet Location

Private Gym and Workspace • 3BR in Quiet Location
Dunning
10.0 out of 10, Exceptional, (1 review)
"Great quiet place. Parking can be trickery. Nice family home. The host is very responsive."
United States
Dr. Kimberly P.
$289 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Private Gym and Workspace • 3BR in Quiet Location

9. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
$220 nightly
The price is $260
Sep 1 - Sep 2
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
A modern living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

10. 2BR Traveler's Favorite • Modern and Clean

2BR Traveler's Favorite • Modern and Clean
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"GET THE GARAGE PARKING! On street parking is non-existant if you plan on driving, The basement 2BR unit we were in was extremely clean and comfortable. It suited our stay perfectly."
United States
Thomas F.
$297 nightly
The price is $367
Aug 31 - Sep 1
Total with taxes and fees
2BR Traveler's Favorite • Modern and Clean
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

11. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
8.8 out of 10, Excellent, (6 reviews)
"G"
United States
Aleah
$258 nightly
The price is $305
Aug 31 - Sep 1
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
A modern living room with a sofa, a round coffee table, a TV mounted on the wall, and a bed with a headboard.

12. Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
$218 nightly
The price is $258
Aug 31 - Sep 1
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
A bedroom with a bed, bedside tables, a nightstand, a potted plant, and a window with curtains.

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

Stylish 3BR Apt | Gym and Workspace | Near O’Hare
Dunning
8.0 out of 10, Very Good, (1 review)
"Overall communication and assistance was great. The couch was advertised as being a pullout but it wasn't. Parking was only available on the street so we always had to park two streets over which was a huge inconvenience. Otherwise everything was great."
United States
Barbara C.
$296 nightly
The price is $350
Aug 31 - Sep 1
Total with taxes and fees
Stylish 3BR Apt | Gym and Workspace | Near O’Hare
A bedroom with a large mirror, a potted plant, a neatly made bed, and a white wall with a power outlet.

14. 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.
$230 nightly
The price is $272
Sep 2 - Sep 3
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace
A modern kitchen with a large island, bar stools, and a city view.

15. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
$289 nightly
The price is $339
Aug 31 - Sep 1
Total with taxes and fees
Level Chicago – Old Town
A modern building with the name 'SENIORAL' prominently displayed on the facade.

16. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,285 reviews)
"Nice stay"
United States
Heather
$177 nightly
The price is $208
Aug 30 - Aug 31
Total with taxes and fees
Sentral Michigan Avenue
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

17. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (226 reviews)
"Great location and newly remodeled, clean rooms."
United States
Brian
$180 nightly
The price is $206
Aug 30 - Aug 31
Total with taxes and fees
The Gem Museum Suites

18. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (20 reviews)
"Great location and super clean!"
United States
Erica
$225 nightly
The price is $268
Sep 7 - Sep 8
Total with taxes and fees
Kasa Lake Shore Chicago
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

19. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
$841 nightly
The price is $1,038
Sep 16 - Sep 17
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments

20. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, and stylish!"
United States
Maurya K.
$416 nightly
The price is $513
Sep 2 - Sep 3
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Clean and accessible"
Duke 3-night trip
Posted 1 hour ago
Club Quarters Hotel, Central Loop, 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 $139 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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