Holiday Homes in Far Southwest Side
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Our top choices for Far Southwest Side holiday homes
Holiday Home in Sauk Village
Your Home Away From Home in Sauk Village10.0 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! "
Aaron K.
The price is AU$221
includes taxes & fees
30 Dec - 31 Dec
Holiday Home in Richton Park
Spacious 3br home near Chicago, fenced yard for pets9.0 out of 10, Wonderful, (14)
"Really cute house! Very comfortable beds. Clean and well maintained. "
Samantha D.
The price is AU$468
includes taxes & fees
5 Jan - 6 Jan 2026
The price is AU$635
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.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."
Karen D.
The price is AU$270
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Worth
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi9.6 out of 10, Exceptional, (55)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is AU$508
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Lockport
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!10.0 out of 10, Exceptional, (5)
"Amazing property had everything we need! "
Rachel
The price is AU$562
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Willow Springs
Coziest estate home 20 minutes to downtown8.8 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!"
Gabriela N.
The price is AU$599
includes taxes & fees
30 Dec - 31 Dec
Holiday Home in La Grange Highlands
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
Arnie B.
The price is AU$398
includes taxes & fees
30 Dec - 31 Dec
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
Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
Find out more about Far Southwest Side
Far Southwest Side Holiday Homes information
Number of reviews | 247 |
|---|---|
Accommodation | 339 Holiday Homes |
Lowest Price | AU$221 |
Highest Price | AU$761 |
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