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

This weekend
Next weekend

Holiday Rentals in Northwest Side

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

The price is AU$1,430
includes taxes & fees
6 Aug - 7 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

Huge Projector and Designated Workspace - Near Wrigley!

The price is AU$441
includes taxes & fees
13 Aug - 14 Aug
Huge Projector and Designated Workspace - Near Wrigley!

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, (860)
"Great stay!"
The price is AU$368
includes taxes & fees
25 Aug - 26 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (338)
"The property canceled on us 4 hours prior to check in"
The price is AU$230
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (335)
"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, (458)
"Kasa apartments are two blocks away from Magnificent mile street. It is a really nice area and there are a lot of attractions close by. We had a wonderful time!!"
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (182)
"Great suite"
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (603)
"I would stay again. "
The price is AU$259
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (325)
"Great stay"
Kasa South Loop Chicago

The Gem Museum Suites

3.5 star property
9.6 out of 10, Exceptional, (82)
"Super nice hotel and staff "
The price is AU$371
includes taxes & fees
14 Aug - 15 Aug
The Gem Museum Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (126)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$291
includes taxes & fees
21 Aug - 22 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, (201)
"Clean, new, spacious "
The price is AU$307
includes taxes & fees
24 Aug - 25 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 AU$276
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (11)
"Excellent location and very clean! Would stay again!"
The price is AU$220
includes taxes & fees
7 Aug - 8 Aug
Wrigleyville Suites

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (159)
"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
8.6 out of 10, Excellent, (43)
"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 AU$230
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Clean & Equipped 1BR Apt

7.6 out of 10, Good, (9)
The price is AU$321
includes taxes & fees
7 Aug - 8 Aug
Clean & Equipped 1BR Apt

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (9)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is AU$344
includes taxes & fees
11 Aug - 12 Aug
Lakeview 2BR Apartment

Cozy, Fully Set-Up 1BR Space

9.4 out of 10, Exceptional, (9)
"Great place! 15 min walk to Wrigley "
The price is AU$321
includes taxes & fees
11 Aug - 12 Aug
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