Photo by throwingsofas

Northwest Side Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Northwest Side

1 bedroom, iron/ironing board, travel cot, WiFi
Prime City Stay in a 1BR Apt
Prime City Stay in a 1BR Apt
9.2 out of 10, Wonderful, (11)
"It was even better than we thought it would be!"
United States
Kelly W.
The price is HK$559
HK$1,391 total
includes taxes & fees
5 Nov - 6 Nov
Prime City Stay in a 1BR Apt
Pool
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
10.0 out of 10, Exceptional, (109)
"Complete apartment with everything you need for the stay. Really quiet well taken care of neighborhood with a short walk to restaurants and grocery. We will plan to stay here for another trip "
United States
Warren & Marta H.
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Smart TV
Central Haven Escape: Stylish 3BR With Free Parking
Central Haven Escape: Stylish 3BR With Free Parking
6.8 out of 10, (6)
"Very nice place and nice host "
United States
Maryo K.
Central Haven Escape: Stylish 3BR With Free Parking
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (578)
"Very great place to stay!"
United States
Edwin
Kasa Magnificent Mile Chicago
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (961)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$1,042
HK$1,452 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (369)
"Friendly staff and great amenities "
United States
Bryan
The price is HK$1,593
HK$2,043 total
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (389)
"Great stay!"
United States
Joe
The price is HK$852
HK$1,000 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (243)
"Great stay. "
United States
Teresa
The price is HK$1,050
HK$1,232 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (693)
"Location was nice."
United States
Juliet
The price is HK$1,050
HK$1,232 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (364)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (211)
"Perfect location and area was wonderful."
United States
Thomas
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
United States
Charles
The price is HK$918
HK$1,078 total
includes taxes & fees
4 Nov - 5 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (173)
"This place has everything for a multi-night stay."
United States
Dane
Kasa River North Chicago
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (185)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is HK$918
HK$1,077 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Private kitchen
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (92)
"Super nice hotel and staff "
United States
EMILY
The price is HK$1,453
HK$1,664 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is HK$483
HK$955 total
includes taxes & fees
23 Oct - 24 Oct
Wrigleyville Suites
Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is HK$1,508
HK$2,638 total
includes taxes & fees
23 Oct - 24 Oct
Stylish Apartment near Chicago Downtown
Living room
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
The price is HK$1,236
HK$1,451 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Property amenity
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
United States
Matthew
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
9.2 out of 10, Wonderful, (28)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
United States
Camron K.
The price is HK$606
HK$1,445 total
includes taxes & fees
11 Nov - 12 Nov
Clean & Equipped 1BR Apt
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Northwest Side Hotel Reviews

Pendry Chicago

Pendry Chicago

10/10 Excellent
"Great staff, excellent guest service, super comfortable. Only one functioning elevator is a concern. "
Larry 3-night trip
Posted 1 day ago
Pendry Chicago

Find out more about Northwest Side

Search for holiday rentals in Northwest Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Northwest Side using one of the methods below:

  • View our selection of featured holiday rentals in Northwest Side
  • Use the map to find apartments and other holiday homes in the Northwest Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Northwest Side while they last

Look no further and take a look at our great range of rental properties in Northwest Side!