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Holiday Homes in Far Southwest Side

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Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Holiday Homes in Far Southwest Side and around

Exterior
A quiet stay while you are away
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is €180
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
2.0 star property
10.0 out of 10, Exceptional, (11)
"We had a wonderful time staying here! Everything looks just like the pictures. The hosts were very accommodating and very good with communication. We would definitely stay here again!"
United States
Amina P.
The price is €181
includes taxes & fees
11 Nov - 12 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms
Honeycomb Hideout w/ 2 bedrooms
The price is €374
includes taxes & fees
6 Nov - 7 Nov
Honeycomb Hideout w/ 2 bedrooms
Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village
Pleasant 3-bedroom house in Sauk Village
2.0 star property
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
United States
Aaron K.
The price is €120
includes taxes & fees
5 Dec - 6 Dec
Pleasant 3-bedroom house in Sauk Village
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.6 out of 10, Exceptional, (53)
"The owner was amazing house was nice and clean everything was perfect we had a really great time!"
United States
Krystal N.
The price is €298
includes taxes & fees
17 Nov - 18 Nov
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
10.0 out of 10, Exceptional, (4)
"Great stay! Clean and comfortable and inviting interior. Very convenient fenced in backyard for our dog. James is a gracious, generous host. I highly recommend this property. "
United States
Brian C.
The price is €338
includes taxes & fees
10 Nov - 11 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior
Coziest estate home 20 minutes to downtown
Coziest estate home 20 minutes to downtown
8.8 out of 10, Excellent, (14)
"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!"
United States
Gabriela N.
The price is €354
includes taxes & fees
6 Nov - 7 Nov
Coziest estate home 20 minutes to downtown
Exterior detail
Vintage Urban Retreat
Vintage Urban Retreat
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is €424
includes taxes & fees
11 Nov - 12 Nov
Vintage Urban Retreat
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (2)
"Very quiet and private and cl9se to alot of things "
United States
Kenneth W.
The price is €261
includes taxes & fees
11 Nov - 12 Nov
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fridge, microwave, oven, stovetop
Superb 3-bedroom house with fitness room in Chicago Heights
Superb 3-bedroom house with fitness room in Chicago Heights
10.0 out of 10, Exceptional, (1)
"Nice house, very responsive owner"
United States
Michael L.
The price is €464
includes taxes & fees
5 Dec - 6 Dec
Superb 3-bedroom house with fitness room in Chicago Heights
Fridge, microwave, oven, stovetop
Spacious 3br home near Chicago, fenced yard for pets
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 "
United States
Marshele W.
The price is €408
includes taxes & fees
9 Nov - 10 Nov
Spacious 3br home near Chicago, fenced yard for pets
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
7.6 out of 10, Good, (12)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
United States
Johanna
The price is €215
includes taxes & fees
6 Nov - 7 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, coffee/tea maker
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
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! "
United States
Amari
The price is €496
includes taxes & fees
6 Nov - 7 Nov
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm
Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (26)
"This was my first time booking here and it was amazing. The host was quick to communicate, and everything was smooth and easy to do. Definitely will book here again the next time my family is in town. "
United States
William K.
The price is €471
includes taxes & fees
17 Nov - 18 Nov
Modern Victorian Vibes ❤️ | Character & Charm
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
The price is €269
includes taxes & fees
10 Nov - 11 Nov
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
The price is €431
includes taxes & fees
10 Nov - 11 Nov
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
Fridge, microwave, oven, stovetop
Spacious Urban Getaway near Downtown
Spacious Urban Getaway near Downtown
2.0 star property
The price is €410
includes taxes & fees
11 Nov - 12 Nov
Spacious Urban Getaway near Downtown
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
The price is €373
includes taxes & fees
9 Nov - 10 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
Smart TV
Enamored in Elmhurst
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"The house is lovely and located in a quiet, nice neighborhood. Our host Mark was very accommodating and responsive. When we informed him thatthe pack-and-play and high chair advertised in the listing were not there, he personally went out and bought new ones, and delivered them. We would certainly stay at this property again.he went out"
United States
Elena L.
The price is €439
includes taxes & fees
6 Nov - 7 Nov
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
The price is €359
includes taxes & fees
1 Dec - 2 Dec
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
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 Far Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Everything was great will definitely stay here again. "
Stephen 1-night trip
Posted 1 day ago
The Royal Sonesta Chicago Downtown

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Far Southwest Side Holiday Homes information

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