Holiday Homes in South Side

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in South Side

LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Private kitchen

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

4.0 out of 10, (4)
"There was room enough for everyone. I like the recording ring doorbell. I like bathroom connect to bedroom. I didn’t like the wide open vent in the floor leading to bathroom. The bathroom door is on backwards. The coffee pot was molded. There were plenty of towels and washcloths. The bed is too close to the wall. The neighborhood is nice and quiet. I probably would stay there again but the price was high for the condition of the house. This house needs a lot of maintenance."
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Fridge, microwave, oven, stovetop

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Large 6 bedroomProsClean & looked new Plenty of space Things to know The neighborhood is not great I would stay here again "
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
House with garage, outdoor dining and basement bar
Fridge, microwave, oven, dishwasher

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar
Cheerful 4 bedroom smart home w/ indoor fireplace
Fridge, microwave, oven, stovetop

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (14)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago/Beverly/Evergreen Park Home
Terrace/patio

Chicago/Beverly/Evergreen Park Home

Chicago/Beverly/Evergreen Park Home
Newly Revamped Home - For privacy lovers
Fridge, microwave, oven, stovetop

Newly Revamped Home - For privacy lovers

10.0 out of 10, Exceptional, (1)
"it was amazing and spacious. it was the perfect home for adults to visit and enjoy themselves."
Newly Revamped Home - For privacy lovers
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Property grounds

Lakefront property , minutes from McCormick Place and Downtown Chicago.

9.8 out of 10, Exceptional, (7)
"Overall great stay, great host"
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
Smart TV, fireplace

Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

10.0 out of 10, Exceptional, (2)
"We were preparing for our organizations annual fundraiser gala. This home was absolutely amazing. The space was appreciated. "
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
“The Marlowe” A Couples Getaway
Property grounds

“The Marlowe” A Couples Getaway

10.0 out of 10, Exceptional, (1)
"Loved everything communication was good definitely a vibe will be booking again "
The price is NZ$782
includes taxes & fees
17 Aug - 18 Aug
“The Marlowe” A Couples Getaway
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Fridge, microwave, oven, stovetop

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

9.8 out of 10, Exceptional, (9)
"Good location"
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Cozy 4BR Home with Crib & Games, Nearby Sights
Fridge, microwave, oven, stovetop

Cozy 4BR Home with Crib & Games, Nearby Sights

Cozy 4BR Home with Crib & Games, Nearby Sights
South Shore Retreat 5 bedrooms/entertainment
Fridge, microwave, oven, stovetop

South Shore Retreat 5 bedrooms/entertainment

8.0 out of 10, Very good, (3)
"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "
South Shore Retreat 5 bedrooms/entertainment
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.0 out of 10, Very good, (9)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
4 bedrooms, desk, iron/ironing board, free WiFi

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (10)
"Everything in the listing was accurate and clean. Easy to check-in and out. Close to food places and venues."
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
This is a totally new rehab
Exterior

This is a totally new rehab

6.4 out of 10, (5)
"Communication with host was excellent. There were several guest # changes and host was very flexible. House was clean and well maintained. Great back porch and yard. We used the gas grill provided and the kitchen was stocked well with dishes, pots and pans, etc. A hot tub was in the listing, but there was no hot tub which was disappointing. The neighbors were friendly and there was public transportation close by. Would definitely book again if we ever get back to Chicago. "
This is a totally new rehab
Lux Home in Chicago 7mins Downtown
Fridge, microwave, oven, stovetop

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (23)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown
Chic & Cozy Chicago Stay: Close to Downtown
Exterior

Chic & Cozy Chicago Stay: Close to Downtown

4.0 out of 10, (1)
"Check in was very unorganized as I was given wrong codes or completely not given codes until asking after arrival. Description inaccurate primarily with 2/3 beds not being queen size as promised. This among other inconveniences from not having a garage remote to finding roaches in the unit. Bugs and webs were a consistent siting during the experience."
Chic & Cozy Chicago Stay: Close to Downtown
Stylish & Comfy Stay: Close to Downtown
Exterior

Stylish & Comfy Stay: Close to Downtown

Stylish & Comfy Stay: Close to Downtown
6 Bedroom Guest House
Fridge, microwave, oven, stovetop

6 Bedroom Guest House

6 Bedroom Guest House
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
"Clean remodeled rooms."
Aicha 3-night trip
Posted 15 hours ago
Motel 6 - Chicago, IL