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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Far Southwest Side vacation homes

Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"great stay"
United States
matt R.
The price is ￥10,354
￥31,380 total
includes taxes & fees
Feb 24 - Feb 25
A quiet stay while you are away
Interior

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 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is ￥34,886
￥105,083 total
includes taxes & fees
Feb 24 - Feb 25
Chic 3bed 2bath Home with free parking close to United Center
Smart TV

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (18 reviews)
"Really cute house! Very comfortable beds. Clean and well maintained. "
United States
Samantha D.
The price is ￥16,745
￥48,268 total
includes taxes & fees
Feb 23 - Feb 24
Spacious 3br home near Chicago, fenced yard for pets
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ￥20,234
￥70,204 total
includes taxes & fees
Feb 23 - Feb 24
Oak Park Victorian by FLW Studio
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ￥11,629
￥80,915 total
includes taxes & fees
Feb 23 - Feb 24
Near Lake and Museum • Modern • Game Area
Property grounds

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (20 reviews)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
The price is ￥24,653
￥34,384 total
includes taxes & fees
Mar 9 - Mar 10
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥22,304
￥61,515 total
includes taxes & fees
Feb 23 - Feb 24
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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
9.4 out of 10, Exceptional, (56 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is ￥24,808
￥52,855 total
includes taxes & fees
Feb 26 - Feb 27
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior

Nice cozy home to experience on your vacation

Nice cozy home to experience on your vacation
Dolton
The price is ￥111,636
￥231,228 total
includes taxes & fees
Feb 23 - Feb 24
Nice cozy home to experience on your vacation
Dining

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
The price is ￥14,885
￥128,634 total
includes taxes & fees
Feb 23 - Feb 24
Sleeps 18 • 8BR • Game Room • Gym • Theater
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (39 reviews)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is ￥19,536
￥45,450 total
includes taxes & fees
Feb 23 - Feb 24
LUXE 3 BR, 2 BA + Hot Tub
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"Great location in a quiet neighborhood! Beautiful Victorian house that was perfect for our company. Every amenities you could ask for and washer/dryer was excellent for our international co founders and they were very impressed with dry time. We will be staying here every time we are in Chicago. "
United States
Mike B.
The price is ￥18,839
￥65,765 total
includes taxes & fees
Feb 23 - Feb 24
Vintage Urban Retreat
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (23 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is ￥16,769
￥42,748 total
includes taxes & fees
Feb 25 - Feb 26
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Exterior

Spacious and Cozy home near O’hare airport

Spacious and Cozy home near O’hare airport
Bensenville
The price is ￥124,040
￥150,191 total
includes taxes & fees
Feb 24 - Feb 25
Spacious and Cozy home near O’hare airport
Interior

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
Lombard
9.6 out of 10, Exceptional, (17 reviews)
"This house was perfect for an intimate family and friends get together."
United States
Alyssa R.
The price is ￥20,188
￥47,357 total
includes taxes & fees
Feb 24 - Feb 25
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
4 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 4-bedroom house with WiFi, AC in welcoming Evanston

Charming 4-bedroom house with WiFi, AC in welcoming Evanston
South Evanston
The price is ￥139,545
￥221,294 total
includes taxes & fees
Feb 23 - Feb 24
Charming 4-bedroom house with WiFi, AC in welcoming Evanston
Fireplace

King Bed, Game Room & Fire Pit | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection
Westchester
8.0 out of 10, Very Good, (2 reviews)
"Great location, price and the place was well kept and accommodating."
United States
Carl M.
The price is ￥34,576
￥78,305 total
includes taxes & fees
Feb 23 - Feb 24
King Bed, Game Room & Fire Pit | LCP Collection
Fridge, microwave, oven, stovetop

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
The price is ￥23,102
￥65,198 total
includes taxes & fees
Mar 10 - Mar 11
Modern Stylish Comfort Near Casino and Hwy
Beach

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, (19 reviews)
"We love it "
United States
sergio o.
The price is ￥24,979
￥69,308 total
includes taxes & fees
Feb 23 - Feb 24
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Smart TV

Enamored in Elmhurst

Enamored in Elmhurst
Elmhurst
10.0 out of 10, Exceptional, (16 reviews)
"Clean rooms, very helpful and friendly host, the house had everything we needed"
United States
Kaitlyn M.
The price is ￥36,592
￥80,846 total
includes taxes & fees
Feb 23 - Feb 24
Enamored in Elmhurst
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"So clean, amazing breakfast - high quality rooms"
Elena 1-night trip
Posted 3 hours ago
Hotel Riu Plaza Chicago

Find out more about Far Southwest Side

Far Southwest Side Vacation Homes information

Number of reviews
319
Accommodation
326 Vacation Homes
Lowest Price
￥31,380
Highest Price
￥231,228

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