Northwest Side Holiday Rentals

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Holiday Rentals in Northwest Side

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is AU$225
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (389)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (639)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (377)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is AU$456
includes taxes & fees
2 Dec - 3 Dec
Chicago luxury home suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is AU$160
includes taxes & fees
1 Dec - 2 Dec
Wrigleyville Suites

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (97)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is AU$289
includes taxes & fees
9 Dec - 10 Dec
The Gem Museum Suites

Clean & Equipped 1BR Apt

Lakeview
9.2 out of 10, Wonderful, (36)
"Perfect for our needs, clean, convenient and great value. "
United States
Lisa B.
The price is AU$246
includes taxes & fees
1 Dec - 2 Dec
Clean & Equipped 1BR Apt

NEW LUXURY PENTHOUSE CONDO

West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is AU$593
includes taxes & fees
2 Dec - 3 Dec
Stylish Apartment near Chicago Downtown

Lakeview 2BR Apartment

Lakeview
9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is AU$278
includes taxes & fees
8 Dec - 9 Dec
Lakeview 2BR Apartment

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$278
includes taxes & fees
8 Dec - 9 Dec
Stylish 1BR in West Loop

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is AU$283
includes taxes & fees
2 Dec - 3 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
United States
Isaiah P.
LakeHouse

Chicago Luxury Penthouse Gold Coast Best Location

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location

Modern West Loop Gem-City Views & Prime Location 6

2.0 star property
Downtown Chicago
Modern West Loop Gem-City Views & Prime Location 6
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

Everything you need to know about Northwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Northwest Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Northwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Northwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Northwest Side holiday rentals we have selected for you start as low as AU$160 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Northwest Side rentals

At Expedia, we put the best Northwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Northwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Northwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Northwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.