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Northwest Side Vacation Rentals

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Our top choices for Northwest Side vacation rentals

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is CA $88
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

2. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is CA $135
CA $469 total
includes taxes & fees
Nov 16 - Nov 17
Sleeps 7 • Huge Projector • Designated Workspace

3. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (10 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is CA $123
CA $311 total
includes taxes & fees
Nov 17 - Nov 18
Relaxing 3BR Getaway Close to Dining & Shopping

4. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is CA $165
CA $825 total
includes taxes & fees
Nov 16 - Nov 17
Theater • Game Room • Gym • Firepit • 4BR Home

5. 1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Perfect but be ready for parking"
United States
Sylvia B.
The price is CA $101
CA $318 total
includes taxes & fees
Dec 1 - Dec 2
1BR Retreat: Roomy & Well-Appointed

6. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 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.
The price is CA $72
CA $387 total
includes taxes & fees
Nov 17 - Nov 18
Studio Near Wrigley • Sleeps 4 • Games • Fireplace

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is CA $217
CA $1,269 total
includes taxes & fees
Nov 17 - Nov 18
Sleeps 18 • 8BR • Game Room • Gym • Theater

8. 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)
"Very clean and comfortable, and great location right next to the blue line."
United States
Jen H.
Pine Beam Sloth Apartment next to Blue Line

9. Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
10.0 out of 10, Exceptional, (1 review)
"Overall experience was wonderful. I would stay again and definitely recommend to anyone traveling to the area 5 stars all around! "
United States
Cristy D.
The price is CA $131
CA $298 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2BR Apartment w/ Washer & Dryer

10. Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
10.0 out of 10, Exceptional, (1 review)
"Nice and spacious thanks again for good commuincation"
United States
Sasha H.
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is CA $157
CA $701 total
includes taxes & fees
Nov 17 - Nov 18
Game Room • Fire-pit • Playground • Gym • Billiard

12. Chic, Quiet 1BR Near Dining Options– Perfect for 2

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Belmont Cragin
2.0 out of 10, (1 review)
"This whole experience of this was the worst possible way to get embarrassed humiliated disrespectful and unprofessional things to happen on your birthday I mean I hope that no one has to endure this"
United States
Durente
The price is CA $121
CA $343 total
includes taxes & fees
Dec 1 - Dec 2
Chic, Quiet 1BR Near Dining Options– Perfect for 2

13. 2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
4.0 out of 10, (1 review)
"Unlisted expenses and check in process, stopped responding after I checked in. Asks unnecessary information about my personal life"
United States
Edward
The price is CA $134
CA $301 total
includes taxes & fees
Nov 16 - Nov 17
2BR Chic & Comfortable Furnished Unit

14. 1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
The price is CA $100
CA $238 total
includes taxes & fees
Nov 17 - Nov 18
1BR 1BA Windy City Hideout

15. Cozy Studio in Portage Park

Cozy Studio in Portage Park
Portage Park
The price is CA $103
CA $227 total
includes taxes & fees
Nov 19 - Nov 20
Cozy Studio in Portage Park

16. Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
The price is CA $147
CA $318 total
includes taxes & fees
Dec 8 - Dec 9
Homey 2BR Apt w/ Parking

17. Lovely 2BR w/ Parking Near United Center & Wrigley

Lovely 2BR w/ Parking Near United Center & Wrigley
Portage Park
The price is CA $113
CA $283 total
includes taxes & fees
Nov 18 - Nov 19
Lovely 2BR w/ Parking Near United Center & Wrigley

18. Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport

Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport
Belmont Cragin
Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport

19. Smart & Stylish 2-Bedroom Unit

Smart & Stylish 2-Bedroom Unit
Irving Park
The price is CA $172
CA $355 total
includes taxes & fees
Nov 16 - Nov 17
Smart & Stylish 2-Bedroom Unit

20. Well-Laid-Out 1BR Apt Near Transit

Well-Laid-Out 1BR Apt Near Transit
Portage Park
The price is CA $108
CA $323 total
includes taxes & fees
Nov 16 - Nov 17
Well-Laid-Out 1BR Apt Near Transit
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Northwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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