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Vacation Homes in Southwest Side

A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is ¥8,798
¥29,112 total
includes taxes & fees
Oct 14 - Oct 15
A quiet stay while you are away
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 ¥21,635
¥30,159 total
includes taxes & fees
Oct 16 - Oct 17
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
The price is ¥18,899
¥60,396 total
includes taxes & fees
Oct 26 - Oct 27
Classic Forest Park Foursquare < 1 Mi to Blue Line
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 ¥10,535
¥41,127 total
includes taxes & fees
Oct 15 - Oct 16
Getaway Near ORD With Great Local Amenities
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
10.0 out of 10, Exceptional, (3)
"Amazing property had everything we need! "
The price is ¥24,946
¥56,006 total
includes taxes & fees
Oct 15 - Oct 16
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Coziest estate home 20 minutes to downtown
8.8 out of 10, Excellent, (13)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
The price is ¥27,214
¥60,653 total
includes taxes & fees
Oct 14 - Oct 15
Coziest estate home 20 minutes to downtown
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (1)
"Very quiet and private and cl9se to alot of things "
The price is ¥15,557
¥41,875 total
includes taxes & fees
Oct 15 - Oct 16
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.6 out of 10, Exceptional, (51)
"Perfect place for an 8 person golf trip! "
The price is ¥23,283
¥50,361 total
includes taxes & fees
Oct 21 - Oct 22
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
7.8 out of 10, Good, (11)
"Very nice place "
The price is ¥22,452
¥35,666 total
includes taxes & fees
Oct 14 - Oct 15
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Spacious 3br home near Chicago, fenced yard for pets
2.0 star property
9.0 out of 10, Wonderful, (13)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is ¥34,290
¥68,708 total
includes taxes & fees
Oct 14 - Oct 15
Spacious 3br home near Chicago, fenced yard for pets
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.4 out of 10, Exceptional, (16)
"Convenient location to family that lives in the area"
The price is ¥15,716
¥41,331 total
includes taxes & fees
Oct 15 - Oct 16
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Updated Spacious Home -Near NWU- Hospitals+More
10.0 out of 10, Exceptional, (2)
"We had a great stay, nice neighborhood, nice home & clean home, fantastic communication with the host. Would stay here again!"
The price is ¥29,633
¥68,767 total
includes taxes & fees
Oct 14 - Oct 15
Updated Spacious Home -Near NWU- Hospitals+More
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (51)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is ¥25,702
¥46,146 total
includes taxes & fees
Oct 21 - Oct 22
✽ Charming Cottage ✽ close to College/Town/Station
Vintage Urban Retreat
10.0 out of 10, Exceptional, (10)
"Loved everything about the place, as advertised in the listing. "
The price is ¥27,990
¥79,643 total
includes taxes & fees
Oct 20 - Oct 21
Vintage Urban Retreat
LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (33)
"The house had a lot of gnats and we were bit up"
The price is ¥23,132
¥51,110 total
includes taxes & fees
Oct 15 - Oct 16
LUXE 3 BR, 2 BA + Hot Tub
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
8.6 out of 10, Excellent, (14)
"i had a good time here. the house was great. thank you"
The price is ¥24,357
¥67,582 total
includes taxes & fees
Oct 14 - Oct 15
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Cicer3bdrm w Pool Table & Shufflle Board
10.0 out of 10, Exceptional, (2)
"Was perfect location to get to and from downtown Chicago, just 30 min with Lyft/Uber. Our 2 dogs did great and had a fenced backyard for them to run. Garage was nice to put our vehicle in. "
The price is ¥32,052
¥80,400 total
includes taxes & fees
Oct 14 - Oct 15
Cicer3bdrm w Pool Table & Shufflle Board
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is ¥32,113
¥75,052 total
includes taxes & fees
Oct 14 - Oct 15
Enamored in Elmhurst
Modern 4BR Retreat Near MDW | LCP Collection
9.4 out of 10, Exceptional, (6)
"Very nice and clean"
The price is ¥27,819
¥74,576 total
includes taxes & fees
Oct 20 - Oct 21
Modern 4BR Retreat Near MDW | LCP Collection
Superb 3-bedroom house with fitness room in Chicago Heights
The price is ¥27,078
¥60,508 total
includes taxes & fees
Oct 14 - Oct 15
Superb 3-bedroom house with fitness room in Chicago Heights
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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