Holiday Homes in Southwest Side

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Featured Holiday Homes in Southwest Side

Our top choices for Southwest Side holiday homes

Sun-Drenched 1BR Apartment

The price is AU$382
includes taxes & fees
22 Sept - 23 Sept
Sun-Drenched 1BR Apartment

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is AU$335
includes taxes & fees
16 Sept - 17 Sept
The One: A 1BR Stay That Feels Like Home

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is AU$370
includes taxes & fees
16 Sept - 17 Sept
Stylish 1BR in West Loop

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (10)
"Very clean in a safe neighborhood. I would stay here again"
The price is AU$308
includes taxes & fees
7 Sept - 8 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is AU$610
includes taxes & fees
11 Sept - 12 Sept
Cozy house in the city

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (26)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is AU$268
includes taxes & fees
9 Sept - 10 Sept
Cozy studio in Andersonville Chicago

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (11)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is AU$702
includes taxes & fees
8 Sept - 9 Sept
Spacious 3br home near Chicago, fenced yard for pets

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is AU$424
includes taxes & fees
6 Oct - 7 Oct
Getaway Near ORD With Great Local Amenities

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is AU$1,021
includes taxes & fees
8 Sept - 9 Sept
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is AU$765
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (15)
"Nice place, interesting neighborhood. Very convenient location!"
Cabin 308 by 747 Lofts

4BR Home with Game Room: Chicago Leisure Escape

7.0 out of 10, Good, (2)
"Smooth and efficient check in and check out process. The property was both super spacious and had several amenities for my guests and I. There are several spots for groceries in the area if your thing is cooking or grilling."
The price is AU$788
includes taxes & fees
7 Sept - 8 Sept
4BR Home with Game Room: Chicago Leisure Escape

Chic apartment with fitness room and AC in beautiful Chicago

7.0 out of 10, Good, (2)
"This was a nice apartment and stay forThe price. Close to train station. However would be nice to add a microwave. I had to reach out by calling the host after no response about check in information on VRBO app. Received the check in information very late the night prior to my stay. Was charged 50 for early check in but when we arrived they were stillCleaning and we had to wait about 15-20minutes outside. Overall with all the inconveniences. It ended up being good stay for the price. "
The price is AU$476
includes taxes & fees
14 Sept - 15 Sept
Chic apartment with fitness room and AC in beautiful Chicago

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (9)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is AU$484
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Homey 1BR Space Apartment

9.2 out of 10, Wonderful, (5)
"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."
The price is AU$299
includes taxes & fees
1 Oct - 2 Oct
Homey 1BR Space Apartment

Elegant 2BR Apartment w/ In-Unit Laundry

10.0 out of 10, Exceptional, (2)
"Super clean. Easy check in. Great location and space. "
The price is AU$344
includes taxes & fees
22 Sept - 23 Sept
Elegant 2BR Apartment w/ In-Unit Laundry

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is AU$318
includes taxes & fees
30 Sept - 1 Oct
Peaceful 1BR Escape in Evanston

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (49)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is AU$499
includes taxes & fees
14 Sept - 15 Sept
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Roscoe Retreat · Cozy 2BR in Chicago

The price is AU$328
includes taxes & fees
7 Sept - 8 Sept
Roscoe Retreat · Cozy 2BR in Chicago

Cozy 2BR Apt w/ Washer & Dryer

The price is AU$332
includes taxes & fees
22 Sept - 23 Sept
Cozy 2BR Apt w/ Washer & Dryer
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

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
Accommodation
412 Holiday Homes
Lowest Price
AU$394
Highest Price
AU$1,349

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