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Southwest Side Holiday Rentals

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Holiday Rentals in Southwest Side

Aparthotel in Downtown Chicago

4.0 star property
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

Aparthotel in Downtown Chicago

4.0 star property
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

Aparthotel in Downtown Chicago

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

Aparthotel in Downtown Chicago

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

Aparthotel in Near West Side

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

Aparthotel in Downtown Chicago

2.0 star property
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$409
includes taxes & fees
30 Nov - 1 Dec
Chicago luxury home suites

Aparthotel in Lakeview

2.0 star property
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
30 Nov - 1 Dec
Wrigleyville Suites

Aparthotel in Downtown Chicago

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

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (97)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is AU$302
includes taxes & fees
30 Nov - 1 Dec
The Gem Museum Suites

Apartment in 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
30 Nov - 1 Dec
Clean & Equipped 1BR Apt

Aparthotel in Harvey

3.0 star property
3.8 out of 10, (67)
"Good "
United States
Abel
The price is AU$125
includes taxes & fees
30 Nov - 1 Dec
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Condo in West Town

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

Aparthotel in Bridgeport

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

Apartment in 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

Aparthotel in West Town

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

Apartment in 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$246
includes taxes & fees
30 Nov - 1 Dec
Stylish 1BR in West Loop

Apartment in 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

Apartment in 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$281
includes taxes & fees
30 Nov - 1 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Holiday Home in 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

Condo in 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
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 Southwest Side Hotel Reviews

Find out more about Southwest Side

Everything you need to know about Southwest 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 Southwest 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 Southwest Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest 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 Southwest 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 Southwest Side holiday rentals we have selected for you start as low as AU$125 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southwest Side rentals

At Expedia, we put the best Southwest 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 Southwest 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 Southwest 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 Southwest 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.