Search Vacation Homes in South Side

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Nov 28 - Nov 30
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Dec 19 - Dec 21
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Jan 16 - Jan 18

Vacation Homes in South Side

Fridge, microwave, oven, stovetop
Stylish 3BR Gem in Prime Location

Vacation Home in Near South Side

$550 nightly
The price is $679
Nov 28 - Nov 29
Total with taxes and fees
Stylish 3BR Gem in Prime Location
Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village

Vacation Home in Sauk Village

2.0 star property
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.
$125 nightly
The price is $134
Nov 23 - Nov 24
Total with taxes and fees
Pleasant 3-bedroom house in Sauk Village
Fridge, microwave, oven, stovetop
Spacious 3br home near Chicago, fenced yard for pets

Vacation Home in Richton Park

2.0 star property
9.0 out of 10, Wonderful, (13)
"Awesome stay!"
United States
Patrick J.
$293 nightly
The price is $313
Nov 20 - Nov 21
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Vacation Home in Whiting

2.0 star property
10.0 out of 10, Exceptional, (12)
"Very clean in a safe neighborhood. I would stay here again"
United States
Charles W.
$128 nightly
The price is $143
Nov 24 - Nov 25
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms

Vacation Home in Gary

$376 nightly
The price is $421
Nov 20 - Nov 21
Total with taxes and fees
Honeycomb Hideout w/ 2 bedrooms
Exterior
A quiet stay while you are away

Vacation Home in Oak Park

9.8 out of 10, Exceptional, (32)
"great stay"
United States
matt R.
$169 nightly
The price is $194
Nov 24 - Nov 25
Total with taxes and fees
A quiet stay while you are away
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park

Vacation Home in 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.
$303 nightly
The price is $308
Dec 1 - Dec 2
Total with taxes and fees
Dunes Escape - Minutes from Indiana Dunes National Park
Outdoor dining
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Vacation Home in Miller Beach

8.6 out of 10, Excellent, (45)
"Great place and great location "
United States
Travis B.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vacation Home in Worth

9.6 out of 10, Exceptional, (53)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$310 nightly
The price is $331
Dec 7 - Dec 8
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Vacation Home in Lockport

10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
United States
Rachel
$367 nightly
The price is $380
Nov 20 - Nov 21
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior
Coziest estate home 20 minutes to downtown

Vacation Home in Willow Springs

8.8 out of 10, Excellent, (14)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
$372 nightly
The price is $398
Nov 20 - Nov 21
Total with taxes and fees
Coziest estate home 20 minutes to downtown
Smart TV
Getaway Near ORD With Great Local Amenities

Vacation Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
$265 nightly
The price is $280
Nov 25 - Nov 26
Total with taxes and fees
Getaway Near ORD With Great Local Amenities
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

7.8 out of 10, Good, (13)
"Very nice place "
United States
Elliot H.
$227 nightly
The price is $242
Nov 20 - Nov 21
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (11)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$423 nightly
The price is $485
Nov 20 - Nov 21
Total with taxes and fees
Vintage Urban Retreat
Exterior
Woodscape Haven · Cozy 3BR Escape

Vacation Home in Miller Beach

10.0 out of 10, Exceptional, (1)
"Lovely, relaxing and clean. Host is very responsive. "
United States
Jennifer L.
$353 nightly
The price is $358
Dec 2 - Dec 3
Total with taxes and fees
Woodscape Haven · Cozy 3BR Escape
Interior
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

2.0 star property
$425 nightly
The price is $517
Nov 20 - Nov 21
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in La Grange Highlands

10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
$253 nightly
The price is $270
Nov 20 - Nov 21
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Beach
Cozy Family Getaway- 4 Blocks From The Beach!

Vacation Home in Miller Beach

$318 nightly
The price is $323
Nov 30 - Dec 1
Total with taxes and fees
Cozy Family Getaway- 4 Blocks From The Beach!
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Vacation Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$294 nightly
The price is $312
Nov 20 - Nov 21
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Game room
Game Room • Fire-pit • Playground • Gym • Billiard

Vacation Home in Belmont Cragin

2.0 star property
$430 nightly
The price is $509
Nov 23 - Nov 24
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
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

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

10/10 Excellent
"Antonio is so great and handsome "
Rashka Sade 1-night trip
Posted 3 days ago
Motel 6 - Chicago, IL

Find out more about South Side

South Side Vacation Homes information

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