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Holiday Homes in Southwest Side
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Our top choices for Southwest Side holiday homes
Spacious 3br home near Chicago, fenced yard for pets
Spacious 3br home near Chicago, fenced yard for petsRichton Park
9.0 out of 10, Wonderful, (14)
"Awesome stay!"
Patrick J.
The price is €272
includes taxes & fees
21 Dec - 22 Dec
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! "
Aaron K.
The price is €129
includes taxes & fees
30 Dec - 31 Dec
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.Robertsdale
9.8 out of 10, Exceptional, (15)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
Karen D.
The price is €174
includes taxes & fees
21 Dec - 22 Dec
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-FiWorth
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is €279
includes taxes & fees
12 Jan - 13 Jan 2026
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! "
Rachel
The price is €332
includes taxes & fees
13 Jan - 14 Jan 2026
Getaway Near ORD With Great Local Amenities
Getaway Near ORD With Great Local AmenitiesDes Plaines
9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
Stephanie G.
The price is €241
includes taxes & fees
11 Jan - 12 Jan 2026
Coziest estate home 20 minutes to downtown
Coziest estate home 20 minutes to downtownWillow 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!"
Gabriela N.
The price is €348
includes taxes & fees
29 Dec - 30 Dec
LUXE 3 BR, 2 BA + Hot Tub
LUXE 3 BR, 2 BA + Hot TubElmhurst
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. "
Scott C.
The price is €246
includes taxes & fees
21 Dec - 22 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 Southwest Side Hotel Reviews
Club Quarters Hotel Wacker at Michigan, Chicago
10/10 Excellent
Find out more about Southwest Side
Southwest Side Holiday Homes information
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