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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
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In four months
Mar 27 - Mar 29

Vacation Homes in South Side

Microwave, oven, stovetop
Your Home Away From Home 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.
The price is ￥14,369
￥22,892 total
includes taxes & fees
Dec 30 - Dec 31
Your Home Away From Home 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.
The price is ￥16,867
￥48,620 total
includes taxes & fees
Dec 15 - Dec 16
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms

Vacation Home in Gary

The price is ￥20,381
￥65,684 total
includes taxes & fees
Dec 2 - Dec 3
Honeycomb Hideout w/ 2 bedrooms
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Vacation Home in Robertsdale

2.0 star property
9.8 out of 10, Exceptional, (15)
"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 ￥22,349
￥31,154 total
includes taxes & fees
Dec 2 - Dec 3
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
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.
The price is ￥13,431
￥48,015 total
includes taxes & fees
Dec 8 - Dec 9
Dunes Escape - Minutes from Indiana Dunes National Park
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.
The price is ￥24,208
￥51,697 total
includes taxes & fees
Dec 2 - Dec 3
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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.
The price is ￥14,837
￥52,483 total
includes taxes & fees
Dec 4 - Dec 5
Woodscape Haven · Cozy 3BR Escape
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
The price is ￥27,332
￥59,180 total
includes taxes & fees
Dec 8 - Dec 9
Lockport Haven/3 King Beds/Wi-fi/Near 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.
The price is ￥10,883
￥43,468 total
includes taxes & fees
Dec 2 - Dec 3
Getaway Near ORD With Great Local Amenities
Exterior
Coziest estate home 20 minutes to downtown

Vacation Home in Willow Springs

8.8 out of 10, Excellent, (15)
"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.
The price is ￥28,112
￥62,153 total
includes taxes & fees
Dec 2 - Dec 3
Coziest estate home 20 minutes to downtown
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (12)
"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 ￥19,946
￥70,751 total
includes taxes & fees
Dec 2 - Dec 3
Vintage Urban Retreat
Fitness facility
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

2.0 star property
The price is ￥14,837
￥85,880 total
includes taxes & fees
Dec 2 - Dec 3
Theater • Game Room • Gym • Firepit • 4BR Home
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

8.0 out of 10, Very Good, (14)
"Very nice place "
United States
Elliot H.
The price is ￥23,193
￥38,011 total
includes taxes & fees
Dec 3 - Dec 4
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Beach
Cozy Family Getaway- 4 Blocks From The Beach!

Vacation Home in Miller Beach

The price is ￥41,075
￥74,473 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy Family Getaway- 4 Blocks From The Beach!
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

Vacation Home in Elmhurst

8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
The price is ￥24,598
￥53,215 total
includes taxes & fees
Dec 4 - Dec 5
LUXE 3 BR, 2 BA + Hot Tub
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
The price is ￥26,551
￥48,166 total
includes taxes & fees
Dec 2 - Dec 3
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Vacation Home in Lisle

9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
The price is ￥16,399
￥41,711 total
includes taxes & fees
Dec 4 - Dec 5
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Vacation Home in Gary

8.6 out of 10, Excellent, (17)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
The price is ￥25,161
￥69,813 total
includes taxes & fees
Dec 2 - Dec 3
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Vacation Home in Wood Dale

10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
The price is ￥27,972
￥61,424 total
includes taxes & fees
Dec 9 - Dec 10
Wonderful in Wood Dale, right by O’Hare airport!
Fridge, microwave, oven, stovetop
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

Vacation Home in Gary

10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
The price is ￥31,767
￥70,564 total
includes taxes & fees
Dec 2 - Dec 3
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
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

Chicago Marriott Midway

Chicago Marriott Midway

10/10 Excellent
"Very convenient and clean and friendly! "
Jennifer 2-night trip
Posted 4 days ago
Chicago Marriott Midway

Find out more about South Side

South Side Vacation Homes information

Number of reviews
268
Accommodation
89 Vacation Homes
Lowest Price
￥22,892
Highest Price
￥85,880

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