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Our top choices for South Side vacation homes

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ¥12,228
¥81,526 total
includes taxes & fees
Feb 4 - Feb 5
Near Lake and Museum • Modern • Game Area

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
The price is ¥22,907
¥58,940 total
includes taxes & fees
Feb 1 - Feb 2
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Honeycomb Hideout w/ 2 bedrooms

Honeycomb Hideout w/ 2 bedrooms
Gary
The price is ¥20,199
¥65,443 total
includes taxes & fees
Feb 1 - Feb 2
Honeycomb Hideout w/ 2 bedrooms

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (33 reviews)
"great stay"
United States
matt R.
The price is ¥9,007
¥29,803 total
includes taxes & fees
Feb 3 - Feb 4
A quiet stay while you are away

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (56 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is ¥22,443
¥49,334 total
includes taxes & fees
Feb 4 - Feb 5
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

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, (20 reviews)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
The price is ¥11,701
¥19,172 total
includes taxes & fees
Feb 2 - Feb 3
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ¥23,898
¥45,433 total
includes taxes & fees
Mar 2 - Mar 3
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

20 min to O'Hare Airport, 20 min to Schamburg

20 min to O'Hare Airport, 20 min to Schamburg
Addison
10.0 out of 10, Exceptional, (2 reviews)
"Definitely recommend!"
United States
Jennifer H.
The price is ¥24,765
¥66,599 total
includes taxes & fees
Feb 2 - Feb 3
20 min to O'Hare Airport, 20 min to Schamburg

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.6 out of 10, Exceptional, (5 reviews)
"Me and my partner had so much fun! The host was very kind, we had our privacy and everything we could've needed during our stay. We truly had a great time! I'd love to come back someday!"
United States
Janina
The price is ¥16,693
¥35,334 total
includes taxes & fees
Feb 2 - Feb 3
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

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, (5 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is ¥22,973
¥53,649 total
includes taxes & fees
Feb 9 - Feb 10
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is ¥22,985
¥74,689 total
includes taxes & fees
Feb 2 - Feb 3
Vintage Urban Retreat

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (28 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ¥23,681
¥74,423 total
includes taxes & fees
Feb 1 - Feb 2
Oak Park Victorian by FLW Studio

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (14 reviews)
"Really cute house! Very comfortable beds. Clean and well maintained. "
United States
Samantha D.
The price is ¥16,716
¥48,184 total
includes taxes & fees
Feb 1 - Feb 2
Spacious 3br home near Chicago, fenced yard for pets

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
8.0 out of 10, Very Good, (21 reviews)
"Very nice place "
United States
Elliot H.
The price is ¥22,985
¥46,447 total
includes taxes & fees
Feb 9 - Feb 10
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
10.0 out of 10, Exceptional, (1 review)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is ¥21,217
¥54,965 total
includes taxes & fees
Feb 1 - Feb 2
Entire home in Lockport, Illinois

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (56 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is ¥26,313
¥47,735 total
includes taxes & fees
Feb 9 - Feb 10
✽ Charming Cottage ✽ close to College/Town/Station

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
The price is ¥20,675
¥60,958 total
includes taxes & fees
Feb 18 - Feb 19
Modern Stylish Comfort Near Casino and Hwy

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ¥16,577
¥43,486 total
includes taxes & fees
Feb 2 - Feb 3
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Gary
8.4 out of 10, Very Good, (19 reviews)
"We love it "
United States
sergio o.
The price is ¥24,935
¥69,533 total
includes taxes & fees
Feb 2 - Feb 3
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions

Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions
Merrillville
10.0 out of 10, Exceptional, (2 reviews)
"Great House, and everything is brand new! Loved the sheets and the towels, and the beds were all super comfy. The outdoor fire pit was a nice touch and made our night a great experience. "
United States
Jim A.
The price is ¥167,162
¥209,931 total
includes taxes & fees
Feb 2 - Feb 3
Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions
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.
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Top South Side Hotel Reviews

Find out more about South Side

South Side Vacation Homes information

Number of reviews
270
Accommodation
91 Vacation Homes
Lowest Price
¥19,172
Highest Price
¥209,931

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