Search Vacation Homes in 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 Southwest Side vacation homes
Vacation Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.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."
Karen D.
The price is ￥16,675
￥24,781 total
includes taxes & fees
Jan 27 - Jan 28
Vacation Home in Oak Park
A quiet stay while you are away9.8 out of 10, Exceptional, (33 reviews)
"great stay"
matt R.
The price is ￥9,060
￥29,980 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Richton Park
Spacious 3br home near Chicago, fenced yard for pets9.0 out of 10, Wonderful, (14 reviews)
"Really cute house! Very comfortable beds. Clean and well maintained. "
Samantha D.
The price is ￥16,816
￥48,971 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Oak Park
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
Willow M.
The price is ￥24,289
￥46,521 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Worth
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi9.6 out of 10, Exceptional, (55 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
David L.
The price is ￥22,577
￥49,628 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in La Grange Highlands
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking10.0 out of 10, Exceptional, (4 reviews)
"very professional hosts and warm accommodations thank you!"
Shawn T.
The price is ￥13,079
￥39,310 total
includes taxes & fees
Jan 26 - Jan 27
The price is ￥3,106
￥66,991 total
includes taxes & fees
Jan 26 - Jan 27
Vacation Home in Westchester
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!9.8 out of 10, Exceptional, (19 reviews)
"Great place Great location "
Josh W.
The price is ￥22,397
￥61,939 total
includes taxes & fees
Jan 26 - Jan 27
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 vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Southwest Side Hotel Reviews
Hilton Chicago/Magnificent Mile Suites
10/10 Excellent
Find out more about Southwest Side
Southwest Side Vacation Homes information
Number of reviews | 325 |
|---|---|
Accommodation | 344 Vacation Homes |
Lowest Price | ￥24,781 |
Highest Price | ￥131,957 |
Explore a world of travel with Expedia
- Cheap Hotels in Essex
- Hotels near Garfield Station
- Luxury Hotels in Grand Boulevard
- Shopping Hotels in South Loop
- Cheap Hotels in Chinatown
- Hostels in Summit
- Hotels near Midway Intl.
- All-Inclusive Hotel Hotels in Englewood
- Hotels near Illinois Institute of Technology
- Family Hotels in South Loop
- Guest Houses in Chicago
- Rv Parks in Chicago
- Resorts in Chicago McCormick Place Station
- B&B in Chicago McCormick Place Station
- Luxury Hotels in Pilsen
- Pet-Friendly Hotels in Chicago
- Condo Rentals in Chicago
- Hotels near Midway Plaisance
- Near West Side Hotels
- Hostels in Chicago
- Historic Hotels in Ashburn
- Aparthotels in South Side
- Cheap Hotels in Englewood
- Hotels near Oriental Institute Museum
- Luxury Hotels in New City
- B&B in Central Chicago
- Illinois Medical District Hotels
- Lower West Side Hotels
- Motels in Chicago McCormick Place Station
- Cheap Hotels in Stickney
- Business Hotels in Hyde Park
- Condo Rentals in Chicago 63rd Street Station
- Pilsen Hotels
- Aparthotels in Chicago Halsted Station
- Inns in Chicago McCormick Place Station
- Aparthotels in Chicago Station
- New City Hotels
- Chalets in Summit
- Town Houses in Chicago
- Boutique Hotels in Little Village
- Bronzeville Hotels
- Business Hotels in New City
- Hotels near Ida B Wells House
- Greektown Hotels
- Hotels near Lakefront Trail
- Hotels near Grant Park
- Palaces in Chicago
- Forest View Hotels
- Adults Only Resorts & in Lower West Side
- Hotels with smoking rooms in Chicago
- All-Inclusive Hotel Hotels in South Loop
- Burbank Hotels
- Apartments in Chicago
- Hotels near University of Illinois Chicago
- Hostels in Forest View
- Boutique Hotels in New City
- Motels in Central Station
- Hostels in Chicago McCormick Place Station
- Golf Hotels in Chicago Lawn
- Chicago Hotels
- Shopping Hotels in Chinatown
- Hotels near Cermak-Chinatown Station
- Oakland Hotels
- Luxury Hotels in Chicago Lawn
- Cheap Hotels in Hyde Park
- Hotels near University of Chicago
- Hotels near Chicago McCormick Place Station
- Washington Park Hotels
- Hotels with Free Parking in Chicago
- Condo Rentals in Evergreen Park
- Aparthotels in Chicago McCormick Place Station
- Hotels near McCormick Place
- Hotels near Chicago 55th-56th-57th Street Station
- Rv Parks in South Side
- Hotels with Early Check-in in South Side
- Hotels with Early Check-in in Chicago
- Family Hotels in Greater Grand Crossing
- Apartments in Chicago 75th Street Station
- Chatham Hotels
- Ashburn Hotels
- Ryokans in Chicago
- Hotels near Burnham Park
- Farmstay in Chicago 63rd Street Station
- Motels in Hometown
- Hotels near Jackson Park
- Hotels near Chicago 35th Street-Lou Jones-Bronzeville Station
- Chinatown Hotels
- Resorts in Forest View
- Aparthotels in Chicago
- Hotels near McCormick Tribune Center
- Hotels near Rush University Medical Center
- Hotel Wedding Venues Hotels in Oakland
- Hotels near Pulaski Station
- Bridgeport Hotels
- Hotels near Rate Field
- Pet-Friendly Hotels in Hyde Park
- Cheap Hotels in Beverly
- Cheap Hotels in Cook County
- Cheap Hotels in Bronzeville
- Hotels near Midway Station