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Search Vacation Homes in Far Southwest Side

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Nov 7 - Nov 9
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Nov 28 - Nov 30
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Dec 26 - Dec 28

Vacation Homes in Far Southwest Side

Exterior
A quiet stay while you are away
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!"
United States
Karigan H.
$168 nightly
The price is $193
Oct 29 - Oct 30
Total with taxes and fees
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)
"Very clean in a safe neighborhood. I would stay here again"
United States
Charles W.
$179 nightly
The price is $201
Oct 30 - Oct 31
Total with taxes and fees
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
$376 nightly
The price is $421
Oct 31 - Nov 1
Total with taxes and fees
Honeycomb Hideout w/ 2 bedrooms
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)
"Amazing property had everything we need! "
United States
Rachel
$406 nightly
The price is $421
Oct 29 - Oct 30
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
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, (52)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$317 nightly
The price is $339
Oct 30 - Oct 31
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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.
$372 nightly
The price is $398
Oct 29 - Oct 30
Total with taxes and fees
Coziest estate home 20 minutes to downtown
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)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
$287 nightly
The price is $307
Nov 11 - Nov 12
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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.
$125 nightly
The price is $134
Oct 29 - Oct 30
Total with taxes and fees
Pleasant 3-bedroom house in Sauk Village
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.
$428 nightly
The price is $458
Nov 2 - Nov 3
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
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.
$244 nightly
The price is $259
Oct 29 - Oct 30
Total with taxes and fees
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.
$408 nightly
The price is $457
Oct 29 - Oct 30
Total with taxes and fees
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
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
7.8 out of 10, Good, (11)
"Very nice place "
United States
Elliot H.
$225 nightly
The price is $240
Oct 29 - Oct 30
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior detail
Vintage Urban Retreat
Vintage Urban Retreat
10.0 out of 10, Exceptional, (11)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$457 nightly
The price is $523
Oct 29 - Oct 30
Total with taxes and fees
Vintage Urban Retreat
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
$376 nightly
The price is $399
Oct 29 - Oct 30
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line
Smart TV
Luxury Suite in Glen Ellyn, IL USA
Luxury Suite in Glen Ellyn, IL USA
9.6 out of 10, Exceptional, (10)
"We have a family of six adults, they have a huge couch where we could all sit comfortably together and watch a movie. We were in for a family wedding and it was nice to all stay together, rather than individual hotel rooms. We highly recommend this location if you need somewhere to stay in the Chicago land area."
United States
Julie T.
Luxury Suite in Glen Ellyn, IL USA
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm
Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (25)
"Great location and walkable to restaurants. "
United States
Laura B.
$467 nightly
The price is $535
Oct 29 - Oct 30
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm
Dining
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
9.6 out of 10, Exceptional, (15)
"Everything was great, most of our activities were a short drive or Uber. The beds and couch was comfortable. It was a nice stay everyone had a good time!"
United States
Israel M.
$275 nightly
The price is $291
Oct 29 - Oct 30
Total with taxes and fees
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
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
$509 nightly
The price is $570
Oct 29 - Oct 30
Total with taxes and fees
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Smart TV
Enamored in Elmhurst
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
$465 nightly
The price is $493
Oct 29 - Oct 30
Total with taxes and fees
Enamored in Elmhurst
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.
$371 nightly
The price is $397
Oct 29 - Oct 30
Total with taxes and fees
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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