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Holiday Homes in Far Southwest Side

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Featured Holiday Homes in Far Southwest Side

Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village

Pleasant 3-bedroom house 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.
The price is NZ$236
includes taxes & fees
23 Nov - 24 Nov
Pleasant 3-bedroom house in Sauk Village
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms

Honeycomb Hideout w/ 2 bedrooms

Gary
The price is NZ$743
includes taxes & fees
15 Nov - 16 Nov
Honeycomb Hideout w/ 2 bedrooms
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
Whiting
10.0 out of 10, Exceptional, (11)
"Beautifully done and lovely owners! Super accommodating. Will definitely return. "
United States
Tim and Becky A.
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior
A quiet stay while you are away

A quiet stay while you are away

Oak Park
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 NZ$343
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away
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
Richton Park
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 NZ$593
includes taxes & fees
17 Nov - 18 Nov
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop
*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, (53)
"We stayed for 9 nights in July 2025 with 4 people and 3 dogs. The home was perfect for us: clean, well-appointed, well-located close to the city, all-one-floor (one of us is handicapped), plenty of parking (even for additional visitors), and a large fenced-in yard. The beds were big and comfortable, plenty of room throughout, plenty of towels, washcloths, etc. The neighborhood is nice, we walked our dogs every day and felt very safe. Just be aware that 111th is a busy street and there is no...
United States
Anonymous traveller
The price is NZ$590
includes taxes & fees
17 Nov - 18 Nov
*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

Willow Springs
8.8 out of 10, Excellent, (14)
"Short"
United States
Brian H.
The price is NZ$703
includes taxes & fees
15 Nov - 16 Nov
Coziest estate home 20 minutes to downtown
Interior
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)
"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 NZ$671
includes taxes & fees
18 Nov - 19 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Hazel Crest
7.4 out of 10, Good, (10)
"Good quiet location "
United States
Augusto D.
The price is NZ$527
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is NZ$834
includes taxes & fees
17 Nov - 18 Nov
Vintage Urban Retreat
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

Maywood
7.8 out of 10, Good, (13)
"Nice house, spacious! Only cons are there aren’t convenient outlets in the rooms to charge your phone while laying down, the front door lock is annoying to lock each time you leave the house, and the lint trap for the dryer tears your clothes. I’d stay again though! P.S. it’s just a little far from downtown (30 minutes) if you’re mostly going out in that area the Ubers/lyfts are costly if you don’t have a rental!"
United States
Nijay C.
The price is NZ$426
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Private kitchen
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.
The price is NZ$474
includes taxes & fees
18 Nov - 19 Nov
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Smart TV
Enamored in Elmhurst

Enamored in Elmhurst

2.0 star property
Elmhurst
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 NZ$871
includes taxes & fees
16 Nov - 17 Nov
Enamored in Elmhurst
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Oak Park
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 NZ$930
includes taxes & fees
2 Dec - 3 Dec
Modern Victorian Vibes ❤️ | Character & Charm
Fridge, microwave, oven, stovetop
Two Kings Chicago A unique royal environment, kingly comfort!

Two Kings Chicago A unique royal environment, kingly comfort!

Villa Park
10.0 out of 10, Exceptional, (1)
"Art & Milda were fantastic hosts! Very responsive to all inquiries and requests. The home was beautiful. Very comfy beds and recliners! So many perks you never knew you wanted. Will definitely stay again. Thank you Art & Milda!"
United States
Lisa V.
The price is NZ$681
includes taxes & fees
17 Nov - 18 Nov
Two Kings Chicago A unique royal environment, kingly comfort!
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

Gary
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
The price is NZ$865
includes taxes & fees
17 Nov - 18 Nov
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
Fridge, microwave, oven, stovetop
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
8.4 out of 10, Very good, (16)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
United States
Alyssa M.
The price is NZ$789
includes taxes & fees
24 Nov - 25 Nov
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Smart TV, video games, table football, ping pong
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK

Your Chicago Hub~ 4 minute Walk to Train~ Pets OK

Brookfield
10.0 out of 10, Exceptional, (2)
"I highly recommend this property! It was the perfect fit for our 6 adults, 4 kids multi-family stay. The house was spacious and beautifully decorated. We commented multiple times throughout our stay at how well stocked the house was. The host was attentive and helpful throughout! We attended events in both downtown Chicago and neighboring suburbs during our stay, and this location was convenient for both. We would definitely stay here again!"
United States
Jill A.
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
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
Gary
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 NZ$1,166
includes taxes & fees
17 Nov - 18 Nov
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, stovetop, dishwasher
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Villa Park
10.0 out of 10, Exceptional, (1)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is NZ$801
includes taxes & fees
17 Nov - 18 Nov
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Room, location, staff all were excellent "
Ellen 1-night trip
Posted 2 days ago
The Whitehall Hotel, BW Premier Collection

Find out more about Far Southwest Side

Far Southwest Side Holiday Homes information

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