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

Holiday Homes in Northwest Side

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Our top choices for Northwest Side holiday homes

1. 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 €500
includes taxes & fees
10 Nov - 11 Nov
Theater • Game Room • Gym • Firepit • 4BR Home

2. 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 €777
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater

3. 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 €401
includes taxes & fees
9 Nov - 10 Nov
Game Room • Fire-pit • Playground • Gym • Billiard

4. 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.
The price is €1,653
includes taxes & fees
4 Dec - 5 Dec
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

5. Quiet Stay - Perfect for Family

Quiet Stay - Perfect for Family
Belmont Cragin
Quiet Stay - Perfect for Family

6. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
The price is €613
includes taxes & fees
9 Nov - 10 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!

7. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is €519
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis

8. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is €181
includes taxes & fees
10 Nov - 11 Nov
Master qtr close to nature & easy urban facilities

9. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is €331
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

10. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is €267
includes taxes & fees
7 Dec - 8 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

11. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is €264
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

12. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Cozy Home | King Bed | 10P | Metra |Chicago Suburb
Highland Hills
9.4 out of 10, Exceptional, (3 reviews)
"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...
United States
Denise G.
The price is €353
includes taxes & fees
18 Nov - 19 Nov
Cozy Home | King Bed | 10P | Metra |Chicago Suburb

13. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €375
includes taxes & fees
10 Nov - 11 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

14. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is €379
includes taxes & fees
9 Nov - 10 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

15. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €223
includes taxes & fees
9 Nov - 10 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

16. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
The price is €519
includes taxes & fees
16 Nov - 17 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

17. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (28 reviews)
"We enjoyed our 2 night stay. The home was exactly what we were expecting. It is on a quiet street and is within walking distance to several restaurants. The beds were comfortable and and the lower level bathroom was especially nice to get ready in."
United States
KIM K.
The price is €276
includes taxes & fees
19 Nov - 20 Nov
Cozy Home by O'Hare + EV Plug

18. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is €306
includes taxes & fees
9 Nov - 10 Nov
LUXE 3 BR, 2 BA + Hot Tub

19. 3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is €336
includes taxes & fees
9 Nov - 10 Nov
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

20. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is €803
includes taxes & fees
9 Nov - 10 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
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

Northwest Side Holiday Homes information

Number of reviews
303
Accommodation
340 Holiday Homes
Lowest Price
€181
Highest Price
€803

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