Photo by throwingsofas

Northwest Side Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Northwest Side

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

2.0 out of 10, (1)
"When I booked this property it was the intention to have a joyful time with my family for an extended family event. We were unable to access the property the day of causing me to spend an extra 600 for us to stay at another hotel after spending 2 hours on the phone with customer service. To top it off we were harassed by the next door neighbor who attempted to take pictures of our vehicle and report to us that this property was considered an illegal listing. Once we gained entry the property was...
The price is NZ$1,600
includes taxes & fees
19 Aug - 20 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Huge Projector and Designated Workspace - Near Wrigley!

The price is NZ$474
includes taxes & fees
18 Aug - 19 Aug
Huge Projector and Designated Workspace - Near Wrigley!

2BR w/ Workspace + Coffee Bar • Near Transit

The price is NZ$630
includes taxes & fees
19 Aug - 20 Aug
2BR w/ Workspace + Coffee Bar • Near Transit

Stylish 3BR + Free Parking 15-20mins from Downtown

2.0 star property
9.4 out of 10, Exceptional, (3)
"Choose to stay near lo"
Stylish 3BR + Free Parking 15-20mins from Downtown

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (875)
"Great stay!"
The price is NZ$381
includes taxes & fees
3 Sept - 4 Sept
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (340)
"The property canceled on us 4 hours prior to check in"
The price is NZ$249
includes taxes & fees
27 Aug - 28 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (338)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (468)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (188)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (611)
"I would stay again. "
The price is NZ$215
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is NZ$385
includes taxes & fees
1 Sept - 2 Sept
The Gem Museum Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (129)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is NZ$332
includes taxes & fees
26 Aug - 27 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (204)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is NZ$293
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (171)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is NZ$265
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (14)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (161)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (46)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is NZ$265
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North

Clean & Equipped 1BR Apt

7.6 out of 10, Good, (10)
The price is NZ$345
includes taxes & fees
3 Sept - 4 Sept
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

8.8 out of 10, Excellent, (14)
"Great place! 15 min walk to Wrigley "
The price is NZ$345
includes taxes & fees
3 Sept - 4 Sept
Cozy, Fully Set-Up 1BR Space
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Northwest Side Hotel Reviews