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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for South Side holiday homes

Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is £427
includes taxes & fees
13 Apr - 14 Apr
Near Lake and Museum • Modern • Game Area
Property grounds

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
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
The price is £137
includes taxes & fees
15 Apr - 16 Apr
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is £182
includes taxes & fees
21 Apr - 22 Apr
A quiet stay while you are away
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
9.4 out of 10, Exceptional, (58 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is £236
includes taxes & fees
12 Apr - 13 Apr
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (40 reviews)
"Nice place, alot of space. Great host"
United States
Devonta J.
The price is £233
includes taxes & fees
14 Apr - 15 Apr
LUXE 3 BR, 2 BA + Hot Tub
Smart TV

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, (23 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is £224
includes taxes & fees
14 Apr - 15 Apr
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (61 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is £229
includes taxes & fees
14 Apr - 15 Apr
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is £448
includes taxes & fees
13 Apr - 14 Apr
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Fridge, microwave, oven, stovetop

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (2 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
The price is £232
includes taxes & fees
14 Apr - 15 Apr
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Smart TV

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, (22 reviews)
"The location was perfect! The house very spacious, with more than enough room for my boys!"
United States
Carmen
The price is £312
includes taxes & fees
13 Apr - 14 Apr
Spacious 3br home near Chicago, fenced yard for pets
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."
United States
Beryl I.
The price is £352
includes taxes & fees
13 Apr - 14 Apr
Vintage Urban Retreat
Dining

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, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is £235
includes taxes & fees
14 Apr - 15 Apr
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
TV

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
7.8 out of 10, Good, (8 reviews)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is £345
includes taxes & fees
14 Apr - 15 Apr
Modern 4BR Retreat Near MDW | LCP Collection
Interior

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
The price is £296
includes taxes & fees
12 Apr - 13 Apr
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Fridge, microwave, oven, stovetop

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)
"Everything was just as expected. Enjoyed our stay."
United States
Eileen W.
The price is £274
includes taxes & fees
12 Apr - 13 Apr
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "
United States
Lawrence P.
The price is £402
includes taxes & fees
13 Apr - 14 Apr
Oak Park Victorian by FLW Studio
Interior

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard
9.6 out of 10, Exceptional, (18 reviews)
"Location was easy to find and good as a base for day trips to Chicago. "
United States
Brian H.
The price is £222
includes taxes & fees
13 Apr - 14 Apr
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (70 reviews)
"Hist was welcoming!House clean and well taken care of!"
United States
Edward H.
The price is £226
includes taxes & fees
13 Apr - 14 Apr
Your Next Vacation Home
Interior

Luxurious Stay 5-min from Airport

Luxurious Stay 5-min from Airport
Indiana
The price is £239
includes taxes & fees
11 May - 12 May
Luxurious Stay 5-min from Airport
Living area

The Hamilton Hideaway at Lake Street Beach

The Hamilton Hideaway at Lake Street Beach
Miller Beach
The price is £398
includes taxes & fees
12 Apr - 13 Apr
The Hamilton Hideaway at Lake Street Beach
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

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"The property had just recently completed a complete renovation. The lobby, rooms, bar/restaurant were immaculate, well-furnished and well maintained. Some sections of the exterior were still being renovated (pool area). The American flag flying in front of the facility was beyond repair and should be replaced or at the least taken down."
William 3-night trip
Posted 23 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

Find out more about South Side

South Side Holiday Homes information

Number of reviews
355
Accommodation
91 Holiday Homes
Lowest Price
£137
Highest Price
£448

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