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

Northwest Side Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Northwest Side holiday rentals

A bedroom with a large mirror, a potted plant, a neatly made bed, and a white wall with a power outlet.

1. Sleeps 4 • New Modern 1BR • Private Workspace

Sleeps 4 • New Modern 1BR • Private Workspace
Irving Park
9.4 out of 10, Exceptional, (3 reviews)
"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.
The price is HK$421
HK$2,250 total
includes taxes & fees
14 Oct - 15 Oct
Sleeps 4 • New Modern 1BR • Private Workspace
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

2. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is HK$552
HK$2,366 total
includes taxes & fees
28 Oct - 29 Oct
Sleeps 7 • Huge Projector • Designated Workspace
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.

3. 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 HK$490
HK$3,016 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A kitchen with a wooden countertop, a sink, and a knife block.

4. 1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
The price is HK$698
HK$1,590 total
includes taxes & fees
5 Oct - 6 Oct
1BR 1BA Windy City Hideout
A kitchen with wooden cabinets, a microwave, stove, oven, and a refrigerator.

5. 1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
The price is HK$581
HK$1,864 total
includes taxes & fees
21 Oct - 22 Oct
1BR Retreat: Roomy & Well-Appointed
A modern living room with a grey sofa, a small side table, a coffee table, and a large window with blinds.

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

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Belmont Cragin
The price is HK$698
HK$2,050 total
includes taxes & fees
26 Oct - 27 Oct
Chic, Quiet 1BR Near Dining Options– Perfect for 2
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

7. 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 HK$661
HK$4,369 total
includes taxes & fees
5 Oct - 6 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
Exterior

8. Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
The price is HK$636
HK$1,507 total
includes taxes & fees
22 Oct - 23 Oct
Stylish 1BR Stay in Irving Vibes
A modern living room with a sectional sofa, a glass coffee table, and a dining area in the background.

9. Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
The price is HK$745
HK$1,792 total
includes taxes & fees
4 Oct - 5 Oct
Cozy 2BR Apartment w/ Washer & Dryer
A modern living room with a blue sofa, a white armchair, a round coffee table with a plant, a flat-screen TV, and abstract wall art.

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

Lovely 2BR w/ Parking Near United Center & Wrigley
Portage Park
The price is HK$792
HK$1,905 total
includes taxes & fees
7 Oct - 8 Oct
Lovely 2BR w/ Parking Near United Center & Wrigley
Room

11. Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!
Portage Park
The price is HK$832
HK$1,677 total
includes taxes & fees
8 Oct - 9 Oct
Comfy Studio in Portage Park- Great Value!
A neatly made bed with white linens and pillows, a headboard with decorative bead trim, a wall-mounted abstract painting, and a bedside table with a lamp and tissues.

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

Well-Laid-Out 1BR Apt Near Transit
Portage Park
The price is HK$855
HK$2,253 total
includes taxes & fees
15 Oct - 16 Oct
Well-Laid-Out 1BR Apt Near Transit
A living room with a dark sofa, a small table with a plant, a radiator, and a window with blinds.

13. 1BR Gem by Shops & Dining

1BR Gem by Shops & Dining
Portage Park
The price is HK$683
HK$2,031 total
includes taxes & fees
5 Oct - 6 Oct
1BR Gem by Shops & Dining
A neatly made bed with a folded white towel, a potted plant, a wall-mounted abstract painting, and a nightstand with a lamp.

14. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (7 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 HK$902
HK$2,113 total
includes taxes & fees
5 Oct - 6 Oct
Relaxing 3BR Getaway Close to Dining & Shopping
A living room with a grey sofa, a wooden coffee table, a ceiling fan, and a radiator.

15. 1BR Apartment with a Warm & Welcoming Feel

1BR Apartment with a Warm & Welcoming Feel
Irving Park
The price is HK$636
HK$1,957 total
includes taxes & fees
6 Oct - 7 Oct
1BR Apartment with a Warm & Welcoming Feel
A compact kitchen with wooden cabinets, a microwave, a stove, and a dining table with chairs.

16. 2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
The price is HK$816
HK$1,875 total
includes taxes & fees
6 Oct - 7 Oct
2BR Chic & Comfortable Furnished Unit
A kitchen with a stove, oven, and microwave. There is a dining table with chairs and a rug. A door leads to another room.

17. Ideal & Spacious 1BR Apt

Ideal & Spacious 1BR Apt
Irving Park
The price is HK$604
HK$1,460 total
includes taxes & fees
6 Oct - 7 Oct
Ideal & Spacious 1BR Apt
A modern living room with a sofa, a coffee table with a plant, a flat-screen TV, and a radiator.

18. Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
The price is HK$816
HK$1,884 total
includes taxes & fees
13 Oct - 14 Oct
Chic 2BR Haven Near Irving Park
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

19. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"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.
The price is HK$421
HK$2,250 total
includes taxes & fees
14 Oct - 15 Oct
Private Workspace • Sleeps4 • Modern Stylish Stay
A neatly made bed with white bedding, two patterned pillows, and a folded white towel. There are two bedside tables with lamps, a decorative wall piece, and a patterned rug on the floor.

20. Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
The price is HK$989
HK$2,115 total
includes taxes & fees
20 Oct - 21 Oct
Homey 2BR Apt w/ Parking
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 Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Older hotel. Everything seemed tight (room, hallways, elevator. Sometimes it takes a while for valet since the drivers had to manage two hotels, averaging around 10-15min. The staff were very friendly though. Would I stay here again? Probably not."
Choua 2-night trip
Posted 7 hours ago
Hotel Saint Clair- Magnificent Mile

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