Search Vacation Homes in Far Southwest Side
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Far Southwest Side vacation homes
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.
$137 nightly
The price is $147
Dec 30 - Dec 31
Total with taxes and fees
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.
$296 nightly
The price is $316
Jan 5 - Jan 6, 2026
Total with taxes and fees
$377 nightly
The price is $422
Dec 28 - Dec 29
Total with taxes and fees
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, (16)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
Karen D.
$160 nightly
The price is $179
Jan 5 - Jan 6, 2026
Total with taxes and fees
*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.
$315 nightly
The price is $337
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$372 nightly
The price is $398
Dec 28 - Dec 29
Total with taxes and fees
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
$364 nightly
The price is $377
Dec 28 - Dec 29
Total with taxes and fees
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 bedMaywood
8.0 out of 10, Very Good, (20)
"Very nice place "
Elliot H.
$221 nightly
The price is $236
Dec 29 - Dec 30
Total with taxes and fees
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.
Top Far Southwest Side Hotel Reviews
Palmer House a Hilton Hotel
10/10 Excellent
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 |
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Motels in Chicago 91st Street Station
- Motels in Chicago 95th Street Station
- Hotels near Chicago Brainerd Station
- Motels in Chicago Gresham Station
- Hotels near Chicago 91st Street Station
- Hotels near Chicago 95th Street Station
- Motels in Chicago 99th Street Station
- Hotels near Washington Heights
- Hotels near Beverly
- 5 Star Hotels in Beverly
- 4 Star Hotels in Beverly
- Hotels near Chicago 99th Street Station
- Hotels near Auburn Gresham
- Motels in 95th-Dan Ryan Station
- Motels in 87th Station
- Hotels near Princeton Park
- Hotels near Chicago 103rd Street Station
- Hotels near 95th-Dan Ryan Station
- Hotels near 87th Station
- Motels in Evergreen Park
- Vacation Homes in Evergreen Park
- Resorts in Evergreen Park
- Apartments in Evergreen Park
- B&B in Evergreen Park
- Hotels near Abbott Park
- Motels in Chicago 111th Street Station
- Hotels near Auburn Park
- Hotels near Chicago 107th Street Station
- Hotels near Roseland
- 5 Star Hotels in Roseland
- 3 Star Hotels in Roseland
- Evergreen Park Hotels
- Omni Hotels in Evergreen Park
- Romantic Hotels in Evergreen Park
- 5 Star Hotels in Evergreen Park
- Extended Stay Hotels in Evergreen Park
- Hotels near 79th Station
- Hotels near Chatham
- 5 Star Hotels in Chatham
- 4 Star Hotels in Chatham
- Hotels near Dauphin Park
- Hotels near Chicago 111th Street Station
- Motels in Chicago 103rd Street Station
- Motels in Chicago 107th Street Station
- B&B in North Pullman
- Hotels near Chicago Wrightwood Station
- Hotels near Chicago 95th Street Station
- Hotels near Morgan Park
- Hotels near Chicago 91st Street Station
- Gay friendly Hotels in Morgan Park
- 4 Star Hotels in Morgan Park
- Hotels near West Englewood
- 3 Star Hotels in West Englewood
- Hotels near Greater Salem Baptist Church
- Hotels near Chicago 103rd Street Station
- Hotels near Chicago 87th Street Station
- Hotels near Chicago 115th Street Station
- Hotels near Greater Grand Crossing
- Motels in Ashland-63rd Station
- Visit Washington Heights
- Visit Beverly
- Visit Princeton Park
- Cook County Vacations
- Visit Cook County
- Visit Roseland
- Visit Evergreen Park
- Visit Chatham
- Visit Dauphin Park
- Visit South Englewood
- South Englewood Vacations
- Visit Chatham Fields
- Visit Morgan Park
- Visit West Englewood
- Greater Salem Baptist Church
- Visit Greater Grand Crossing
- Car rentals near Chicago
- Car rentals near Washington Heights
- Car rentals near Beverly
- Car rentals near Auburn Gresham
- Car rentals near Gresham
- Car rentals near Garden Homes
- Car rentals near Roseland
- Luxury Car Rentals in Roseland
- Car rentals near Evergreen Park
- Enterprise Rental Cars in Evergreen Park
- Sixt Rental Cars in Evergreen Park
- National Car Rental Rental Cars in Evergreen Park
- Avis Rental Cars in Evergreen Park
- Car rentals near Chatham
- Car rentals near Dauphin Park
- Car rentals near Chatham Fields
- Car rentals near Morgan Park
- Pickup Car Rentals near Roseland Community Hospital
- Car rental Chicago Airport (MDW)