Holiday rentals with weekly discounts – Far Southwest Side
Showing deals for:12 Feb - 19 Feb
Image gallery for 5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
5 bedrooms/ 3 bathrooms/2 living rooms Elegant Escape at Burr Ridge/ La Grange
Burr Ridge
8% off
Price is AU$5,030
AU$5,030
for 7 nights, 1 home
AU$719 per night
includes taxes & fees
Image gallery for Spacious 4BR Bronzeville Home - Sleeps 10 - Near McCormick Place
9.49.4 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Spacious 4BR Bronzeville Home - Sleeps 10 - Near McCormick Place
Chicago
8% off
Price is AU$5,156
AU$5,156
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Image gallery for Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Bronzeville-Lakefront property, near Sox, McCormick, Museums & Downtown Chicago.
Chicago
11% off
Price is AU$6,414
AU$6,414
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.89.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago
8% off
Price is AU$6,149
AU$6,149
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
Image gallery for Spacious home 28 miles from Downtown Chicago
9.69.6 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)
Spacious home 28 miles from Downtown Chicago
Hammond
8% off
Price is AU$3,785
AU$3,785
for 7 nights, 1 home
AU$541 per night
includes taxes & fees
Image gallery for Beautiful Berwyn Bungalow Close to Downtown Chicago
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Beautiful Berwyn Bungalow Close to Downtown Chicago
Berwyn
8% off
Price is AU$3,408
AU$3,408
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Image gallery for 5 bedroom with 5 beds and 2 bathrooms
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
5 bedroom with 5 beds and 2 bathrooms
Oak Park
8% off
Price is AU$5,597
AU$5,597
for 7 nights, 1 apartment
AU$800 per night
includes taxes & fees
Image gallery for Steps to Shops, Restaurants, Trains; 5BR, 14 Guests, Parking
9.69.6 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Steps to Shops, Restaurants, Trains; 5BR, 14 Guests, Parking
Forest Park
29% off
Price is AU$4,538
AU$4,538
for 7 nights, 1 home
AU$648 per night
includes taxes & fees
Image gallery for The En Bronze ~ 7mins To Dining & Downtown Chicago
9.29.2 out of 10, Wonderful, (9 reviews)
Wonderful
(9 reviews)
The En Bronze ~ 7mins To Dining & Downtown Chicago
Chicago
7% off
Price is AU$5,909
AU$5,909
for 7 nights, 1 apartment
AU$844 per night
includes taxes & fees
Image gallery for Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
8% off
Price is AU$1,665
AU$1,665
for 7 nights, 1 apartment
AU$238 per night
includes taxes & fees
Image gallery for 3bed/1 bath Retreat - 10 min from Downtown
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
3bed/1 bath Retreat - 10 min from Downtown
Chicago
8% off
Price is AU$3,091
AU$3,091
for 7 nights, 1 apartment
AU$442 per night
includes taxes & fees
Image gallery for Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
Chicago
10% off
Price is AU$3,032
AU$3,032
for 7 nights, 1 apartment
AU$433 per night
includes taxes & fees
Image gallery for Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
9.69.6 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Chicago
8% off
Price is AU$2,155
AU$2,155
for 7 nights, 1 home
AU$308 per night
includes taxes & fees
Image gallery for 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
9.49.4 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Chicago
7% off
Price is AU$3,382
AU$3,382
for 7 nights, 1 apartment
AU$483 per night
includes taxes & fees
Image gallery for Modern Apt Near U of Chicago!
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Modern Apt Near U of Chicago!
Chicago
7% off
Price is AU$2,150
AU$2,150
for 7 nights, 1 apartment
AU$307 per night
includes taxes & fees
Image gallery for Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
9.09.0 out of 10, Wonderful, (45 reviews)
Wonderful
(45 reviews)
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
8% off
Price is AU$1,958
AU$1,958
for 7 nights, 1 apartment
AU$280 per night
includes taxes & fees
Image gallery for Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
9.89.8 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Chicago
7% off
Price is AU$1,988
AU$1,988
for 7 nights, 1 apartment
AU$284 per night
includes taxes & fees
Image gallery for High-end 2Bdrm Garden Apt. Where Comfort Meets Style
9.29.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Chicago
7% off
Price is AU$2,073
AU$2,073
for 7 nights, 1 apartment
AU$296 per night
includes taxes & fees
Image gallery for Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
9.69.6 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
8% off
Price is AU$1,712
AU$1,712
for 7 nights, 1 apartment
AU$245 per night
includes taxes & fees
Image gallery for Stylish 2BR Near Hyde Park, UChicago & Lake
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Stylish 2BR Near Hyde Park, UChicago & Lake
Chicago
7% off
Price is AU$1,503
AU$1,503
for 7 nights, 1 apartment
AU$215 per night
includes taxes & fees
Image gallery for Ridgeland Retreat/ Street level Apt easy access
9.29.2 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)
Ridgeland Retreat/ Street level Apt easy access
Berwyn
8% off
Price is AU$2,466
AU$2,466
for 7 nights, 1 apartment
AU$352 per night
includes taxes & fees
Image gallery for 1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
1010 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Chicago
7% off
Price is AU$5,081
AU$5,081
for 7 nights, 1 apartment
AU$726 per night
includes taxes & fees
Image gallery for Vibrant 3BR Pilsen Stay•Free Parking•Near Downtown
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Vibrant 3BR Pilsen Stay•Free Parking•Near Downtown
Chicago
7% off
Price is AU$3,001
AU$3,001
for 7 nights, 1 apartment
AU$429 per night
includes taxes & fees
Image gallery for Chicago style apt/Near Hosp/ORD/MDW/DT
8.48.4 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
Chicago style apt/Near Hosp/ORD/MDW/DT
Berwyn
8% off
Price is AU$1,786
AU$1,786
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Loading
Find the best place to stay - Far Southwest Side
1. Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
Sleeps 2 · 2 bedrooms · 2+ bathrooms
8.88.8 out of 10
Excellentexcellent
15 reviews(15 reviews)
2. Hidden Gem OASIS 40 minutes away from Chicago
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
3. Mokena Manor: Luxury Living - Your Elite Escape!
Sleeps 15 · 7 bedrooms · 5+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
4. Full Luxurious Modern Home+Free Parking/Fast Wi-Fi+Centrally located+Free Washer
Sleeps 12 · 4 bedrooms · 2 bathrooms
4.04.0 out of 10
2 reviews(2 reviews)
5. Gorgeous Log Home in Chicagoland!
Sleeps 6 · 4 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
33 reviews(33 reviews)
6. Dream Stay - Modern Bungalow Near Downtown
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently Asked Questions
How much does it cost to rent a holiday home in Far Southwest Side?
The average price for a holiday home in Far Southwest Side depends on several factors, such as property type, season and length of stay. Whether you're in search of a sprawling villa with lots of space or a comfy cabin for you and your other half, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Far Southwest Side?
Prices for beach houses in Far Southwest Side may vary depending on the size and type of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and how many guests to view holiday home options and prices. From there you can use the filters to refine your search by ratings, nearby activities, amenities and more.
How old do you have to be to rent a holiday home in Far Southwest Side?
We recommend checking with the Far Southwest Side holiday property you're looking at on Stayz as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Far Southwest Side for?
It's really down to the Far Southwest Side property. To view all available options offering extended stays, simply enter your travel dates and number of guests into Stayz's search page. Enjoy having the whole place to yourself, along with comforts such as a full kitchen, air conditioning and a yard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.