South Side Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for South Side vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,173 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is P9,388
P12,831 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (481 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is P10,444
P13,783 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (125 reviews)
"Perfect place to stay!"
United States
Anton
The price is P9,328
P10,679 total
includes taxes & fees
May 26 - May 27
The Gem Museum Suites
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (193 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is P11,771
P18,888 total
includes taxes & fees
May 27 - May 28
Kasa River North Chicago
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (37 reviews)
"Amazing !!!!! Would stay again, clean, beautiful Spot, great area !"
United States
Luka
The price is P6,719
P7,887 total
includes taxes & fees
May 26 - May 27
Wrigleyville Suites
Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is P16,437
P25,668 total
includes taxes & fees
May 31 - Jun 1
Historic Oak Park Residence
Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
The price is P7,502
P12,890 total
includes taxes & fees
Jun 10 - Jun 11
Cabin 105 by 747 Lofts
Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is P12,443
P21,097 total
includes taxes & fees
Jun 9 - Jun 10
Historic Oak Park Home
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is P12,443
P21,097 total
includes taxes & fees
May 26 - May 27
The Oak Park Loft
Exterior

River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
The price is P9,027
P20,738 total
includes taxes & fees
Jun 2 - Jun 3
River West, Second Floor Chicago by 747 Lofts
Exterior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is P13,729
P26,534 total
includes taxes & fees
May 31 - Jun 1
River West, Third Floor Chicago by 747 Lofts
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

4/10 Poor
"Check in desk had one (1) poor soul, who was clearly moving slow & concentrating intensely…..betraying the fact that he was new (and left to fend for himself on the Friday night of Memorial Day weekend). One elevator was out of commission. The restaurant was swarmed for breakfast & couldn’t keep the mob from getting frustrated by the lack of available warm food (unless you chose to try & toast an English muffin with a toaster that couldn’t warm up a pat of butter if it were placed on the top). Bad all the way around. Avoid this sad hulk of a property that now dishonors the name Marriott."
Matthew 1-night trip
Posted 14 hours ago
Chicago Marriott Midway

Find out more about South Side

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