Southwest Side Vacation Rentals
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Our top choices for Southwest Side vacation rentals
1. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
Yiu S.
The price is ￥13,911
￥39,035 total
includes taxes & fees
Nov 1 - Nov 2
9.0 out of 10, Wonderful, (1,374 reviews)
"Perfect location to stay at if attending the bears games !"
Jacob
The price is ￥22,637
￥26,572 total
includes taxes & fees
Nov 11 - Nov 12
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
Iliana
The price is ￥28,296
￥41,545 total
includes taxes & fees
Nov 1 - Nov 2
4. Chic Suite/Mins to L Train /Laundry/Free Parking
Chic Suite/Mins to L Train /Laundry/Free ParkingOak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
Michael
The price is ￥15,934
￥38,149 total
includes taxes & fees
Oct 21 - Oct 22
5. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/ParkingLakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
Bridget
The price is ￥16,047
￥33,376 total
includes taxes & fees
Nov 3 - Nov 4
6. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal SpotWest Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
Francis
The price is ￥15,810
￥39,792 total
includes taxes & fees
Oct 20 - Oct 21
7. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6West Town
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
Jessica C.
The price is ￥17,391
￥37,634 total
includes taxes & fees
Nov 4 - Nov 5
8. 2BR Apt with 2 Baths & Laundry
2BR Apt with 2 Baths & LaundryNear West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
michele
The price is ￥16,598
￥38,939 total
includes taxes & fees
Nov 2 - Nov 3
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
The Chicago Hotel Collection Ambassador Gold Coast
8/10 Good
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