Holiday Homes in Far Southwest Side
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Far Southwest Side holiday homes
1. 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, (31 reviews)
"I had a fun stay "
Jusu K.
The price is AU$283
includes taxes & fees
25 Aug - 26 Aug
2. *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-FiWorth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
Joe M.
The price is AU$587
includes taxes & fees
24 Aug - 25 Aug
3. ENVITAE Hotel, 4BR Luxury Modern Apartments
ENVITAE Hotel, 4BR Luxury Modern ApartmentsNear North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
Pedro C.
The price is AU$1,402
includes taxes & fees
16 Sept - 17 Sept
4. 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, (32 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing.
Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix)
All in all it was a good stay."
Amal
The price is AU$420
includes taxes & fees
24 Aug - 25 Aug
5. 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
9.4 out of 10, Exceptional, (22 reviews)
"Great location and the place was immaculate. Host was very nice."
Carl M.
The price is AU$609
includes taxes & fees
24 Aug - 25 Aug
6. Charming & Cozy Getaway - A Heroic Stay Awaits!
Charming & Cozy Getaway - A Heroic Stay Awaits!Homewood
10.0 out of 10, Exceptional, (20 reviews)
"We had such a lovely stay. It was cute, quaint, and the perfect place to spend Mother’s Day with my mother. The space was cozy, clean, and had such a peaceful charm to it. We truly enjoyed our time here and would absolutely stay again!"
Nikki B.
The price is AU$553
includes taxes & fees
8 Sept - 9 Sept
7. Sleeps 18 • 7BR • Gym • Game Room • Theater
Sleeps 18 • 7BR • Gym • Game Room • TheaterAustin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
Adrian Cesar C.
The price is AU$1,276
includes taxes & fees
24 Aug - 25 Aug
8. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private BackyardOak Park
10.0 out of 10, Exceptional, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
Willow M.
The price is AU$477
includes taxes & fees
7 Sept - 8 Sept
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.
Find holiday rentals that suit your style
Apartments
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Far Southwest Side Hotel Reviews
The Royal Sonesta Chicago Downtown
10/10 Excellent
Find out more about Far Southwest Side
Far Southwest Side Holiday Homes information
Number of reviews | 26,911 |
|---|---|
Accommodation | 355 Holiday Homes |
Lowest Price | AU$125 |
Highest Price | AU$350 |
Explore a world of travel with Expedia
- B&B in Bloomingdale
- Blue Island Hotels
- Motels in Braidwood
- Central Station Hotels
- Apartments in Chicago
- Accor Hotels in Chicago
- Cheap Hotels in Chicago
- Historic Hotels in Chicago
- Luxury Hotels in Chicago
- Chicago Hotels
- Motels in Chicago
- Hotels near Chicago Riverwalk
- Serviced Apartments in Chicago
- Hotels near Chicago Theatre
- Chinatown Hotels
- Countryside Hotels
- Crestwood Hotels
- Cheap Hotels in Downtown Chicago
- Downtown Chicago Hotels
- B&B in Glenview
- Fairmont Hotels in Gold Coast
- Four Seasons Hotels in Gold Coast
- Swissotel Hotels in Gold Coast
- Hotels near Grant Park
- Harvey Hotels
- Homewood Hotels
- B&B in Island Lake
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Hotels near Michigan Avenue
- Hotels near Millennium Park
- Hotels near Navy Pier
- Near South Side Hotels
- River North Hotels
- Apartments in Serena
- Hotels near Soldier Field
- South Loop Hotels
- The Loop Hotels
- Theatre District Hotels
- United Center Hotels
- Hotels near University of Chicago
- Motels in Waterman
- Flights to Blue Island
- Flights to Bridgeview
- Flights to Chicago
- Flights from Midway Intl.
- Flights from O'Hare Intl.
- Flights from Chicago
- Flights from Adelaide (ADL) to Chicago (ORD)
- Flights from Brisbane (BNE) to Chicago (ORD)
- Flights from Burbank (BUR) to Chicago (MDW)
- Flights from Charleston (CRW) to Chicago (MDW)
- Flights from Denver (DEN) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Melbourne (MEL) to Chicago (ORD)
- Flights from Perth (PER) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Sydney (SYD) to Chicago (ORD)
- Abbott Park
- Art Institute of Chicago
- Buckingham Fountain
- Visit Armour Square
- Visit Canaryville
- Visit Downtown Chicago
- Visit Gold Coast
- Visit Grand Boulevard
- Visit Jackson Park Highlands
- Visit Magnificent Mile
- Visit River North
- Chicago Riverwalk
- Visit South Loop
- Visit The Loop
- Visit West Loop
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Downtown Chicago Holidays
- Garfield Park Conservatory
- Gold Coast Holidays
- Grant Park
- Griffin Museum of Science and Industry
- Millennium Park
- Navy Pier
- Oak Street Beach
- Pullman Holidays
- University of Illinois Chicago
- Willis Tower