Search Vacation Homes in Far Southwest Side

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Our top choices for Far Southwest Side vacation homes

Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village
2.0 star property
Sauk Village
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.
$137 nightly
The price is $147
Dec 30 - Dec 31
Total with taxes and fees
Your Home Away From Home in Sauk Village

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
2.0 star property
Richton Park
9.0 out of 10, Wonderful, (14)
"Awesome stay!"
United States
Patrick J.
$296 nightly
The price is $316
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets

Honeycomb Hideout w/ 2 bedrooms

Honeycomb Hideout w/ 2 bedrooms
Gary
$377 nightly
The price is $422
Dec 28 - Dec 29
Total with taxes and fees
Honeycomb Hideout w/ 2 bedrooms

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
Robertsdale
9.8 out of 10, Exceptional, (16)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
$160 nightly
The price is $179
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

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

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$315 nightly
The price is $337
Jan 4 - Jan 5, 2026
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown
Willow Springs
8.8 out of 10, Excellent, (16)
"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
Dec 28 - Dec 29
Total with taxes and fees
Coziest estate home 20 minutes to downtown

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
United States
Rachel
$364 nightly
The price is $377
Dec 28 - Dec 29
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

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
Maywood
8.0 out of 10, Very Good, (20)
"Very nice place "
United States
Elliot H.
$221 nightly
The price is $236
Dec 29 - Dec 30
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$489 nightly
The price is $560
Jan 12 - Jan 13, 2026
Total with taxes and fees
Vintage Urban Retreat

Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
2.0 star property
Lockport
$313 nightly
The price is $332
Jan 12 - Jan 13, 2026
Total with taxes and fees
Entire home in Lockport, Illinois

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
2.0 star property
Belmont Cragin
$416 nightly
The price is $492
Jan 14 - Jan 15, 2026
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard

Gated Family Home w/ Chef’s Kitchen

Gated Family Home w/ Chef’s Kitchen
2.0 star property
Humboldt Park
$500 nightly
The price is $515
Jan 11 - Jan 12, 2026
Total with taxes and fees
Gated Family Home w/ Chef’s Kitchen

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
9.4 out of 10, Exceptional, (6)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
$428 nightly
The price is $458
Jan 11 - Jan 12, 2026
Total with taxes and fees
Modern 4BR Retreat Near MDW | LCP Collection

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
La Grange Highlands
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.
$270 nightly
The price is $289
Dec 28 - Dec 29
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Gary
8.6 out of 10, Excellent, (17)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
$400 nightly
The price is $448
Dec 25 - Dec 26
Total with taxes and fees
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (18)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
$592 nightly
The price is $678
Dec 27 - Dec 28
Total with taxes and fees
Chic 3bed 2bath Home with free parking close to United Center

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
Gary
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
$405 nightly
The price is $454
Jan 6 - Jan 7, 2026
Total with taxes and fees
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
$344 nightly
The price is $368
Jan 1 - Jan 2, 2026
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub

Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm
Oak Park
10.0 out of 10, Exceptional, (28)
"Great location and walkable to restaurants. "
United States
Laura B.
$508 nightly
The price is $582
Jan 13 - Jan 14, 2026
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
Portage Park
$757 nightly
The price is $922
Jan 13 - Jan 14, 2026
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
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

Find out more about Far Southwest Side

Far Southwest Side Vacation Homes information

Number of reviews
240
Accommodation
326 Vacation Homes
Lowest Price
$147
Highest Price
$922

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