Search Vacation Homes in South Side

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar
Fridge, microwave, oven, stovetop
Stylish 3BR Gem in Prime Location

Stylish 3BR Gem in Prime Location

Near South Side
The price is HK$2,449
HK$5,343 total
includes taxes & fees
28 Nov - 29 Nov
Stylish 3BR Gem in Prime Location
Exterior detail
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.

2.0 star property
Whiting
10.0 out of 10, Exceptional, (11)
"Beautifully done and lovely owners! Super accommodating. Will definitely return. "
United States
Tim and Becky A.
The price is HK$693
HK$1,080 total
includes taxes & fees
18 Nov - 19 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village

Pleasant 3-bedroom house in Sauk Village

2.0 star property
Sauk Village
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! "
United States
Aaron K.
The price is HK$622
HK$1,040 total
includes taxes & fees
23 Nov - 24 Nov
Pleasant 3-bedroom house in Sauk Village
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms

Honeycomb Hideout w/ 2 bedrooms

Gary
The price is HK$1,014
HK$3,269 total
includes taxes & fees
17 Nov - 18 Nov
Honeycomb Hideout w/ 2 bedrooms
Exterior
A quiet stay while you are away

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is HK$460
HK$1,505 total
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away
Fridge, microwave, oven, stovetop
Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
Richton Park
9.0 out of 10, Wonderful, (13)
"Nice property easy check in. Experience was amazing. Thank you again "
United States
Marshele W.
The price is HK$993
HK$2,609 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 3br home near Chicago, fenced yard for pets
Interior
Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home

2.0 star property
Belmont Cragin
The price is HK$505
HK$3,943 total
includes taxes & fees
19 Nov - 20 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park

Dunes Escape - Minutes from Indiana Dunes National Park

Miller Beach
9.8 out of 10, Exceptional, (36)
"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"
United States
Braden S.
The price is HK$684
HK$2,423 total
includes taxes & fees
1 Dec - 2 Dec
Dunes Escape - Minutes from Indiana Dunes National Park
Interior
Sleeps 18 • 8BR • Game Room • Gym • Theater

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

2.0 star property
Portage Park
The price is HK$1,026
HK$6,664 total
includes taxes & fees
18 Nov - 19 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
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
9.6 out of 10, Exceptional, (53)
"The owner was amazing house was nice and clean everything was perfect we had a really great time!"
United States
Krystal N.
The price is HK$1,205
HK$2,598 total
includes taxes & fees
17 Nov - 18 Nov
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Smart TV
Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."
United States
Dorde U.
The price is HK$542
HK$2,163 total
includes taxes & fees
19 Nov - 20 Nov
Getaway Near ORD With Great Local Amenities
Exterior
Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown

Willow Springs
8.8 out of 10, Excellent, (14)
"Short"
United States
Brian H.
The price is HK$1,399
HK$3,093 total
includes taxes & fees
18 Nov - 19 Nov
Coziest estate home 20 minutes to downtown
Interior
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)
"Great stay! Clean and comfortable and inviting interior. Very convenient fenced in backyard for our dog. James is a gracious, generous host. I highly recommend this property. "
United States
Brian C.
The price is HK$1,314
HK$2,921 total
includes taxes & fees
17 Nov - 18 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Hazel Crest
7.4 out of 10, Good, (10)
"Good quiet location "
United States
Augusto D.
The price is HK$793
HK$2,320 total
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Beach
Cozy Family Getaway- 4 Blocks From The Beach!

Cozy Family Getaway- 4 Blocks From The Beach!

Miller Beach
The price is HK$1,011
HK$2,507 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Getaway- 4 Blocks From The Beach!
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is HK$1,093
HK$3,645 total
includes taxes & fees
18 Nov - 19 Nov
Vintage Urban Retreat
Exterior
Woodscape Haven · Cozy 3BR Escape

Woodscape Haven · Cozy 3BR Escape

Miller Beach
10.0 out of 10, Exceptional, (1)
"Lovely, relaxing and clean. Host is very responsive. "
United States
Jennifer L.
The price is HK$894
HK$2,785 total
includes taxes & fees
1 Dec - 2 Dec
Woodscape Haven · Cozy 3BR Escape
Microwave, oven, stovetop, dishwasher
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 bed

Maywood
7.8 out of 10, Good, (13)
"This space was perfect for our short stay in the city; plenty of parking space for our vehicles in a nice neighborhood, a quaint living room for socializing before and after our event and comfortable beds overnight. Although we didn’t take advantage, the downstairs bar would have been a cool space for a night cap. The host was very amenable, responsive and supportive. "
United States
Michael M.
The price is HK$1,154
HK$1,875 total
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

La Grange Highlands
10.0 out of 10, Exceptional, (2)
"Very quiet and private and cl9se to alot of things "
United States
Kenneth W.
The price is HK$653
HK$1,979 total
includes taxes & fees
17 Nov - 18 Nov
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale
10.0 out of 10, Exceptional, (17)
"Our stay was great I will 100% recommend staying here!"
United States
Taylor W.
The price is HK$1,392
HK$3,057 total
includes taxes & fees
19 Nov - 20 Nov
Wonderful in Wood Dale, right by O’Hare airport!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"The staff is always courteous, helpful, professional, and genuinely nice. I am there on a weekly basis and always feel welcomed. I appreciate how they value my business. Most importantly I love that their eyes smile like their happy to help."
Chequrita 1-night trip
Posted 2 days ago
Hyatt Place Chicago-South/University Medical Center

Find out more about South Side

South Side Vacation Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia