South Side Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select South Side Vacation Homes

2 Connecting Suites at a 4⭐️ Hotel
Banquet hall

2 Connecting Suites at a 4⭐️ Hotel

The price is CA $757
CA $1,022 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 4⭐️ Hotel
2 Connecting Suites at a 5⭐️ Hotel
Exterior

2 Connecting Suites at a 5⭐️ Hotel

The price is CA $3,653
CA $4,930 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 5⭐️ Hotel
Stylish 4BR South Loop Home State 23-202
Fridge, microwave, oven, stovetop

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
The price is CA $189
CA $577 total
includes taxes & fees
Sep 3 - Sep 4
Stylish 4BR South Loop Home State 23-202
Hyde Park Haven | 2BR Retreat
Fridge, microwave, oven, stovetop

Hyde Park Haven | 2BR Retreat

8.0 out of 10, Very good, (1)
"Very neat and nicely decorated, only a couple of issues"
The price is CA $135
CA $312 total
includes taxes & fees
Aug 25 - Aug 26
Hyde Park Haven | 2BR Retreat
1BR in Prime Hyde Park Apt
1 bedroom, iron/ironing board, travel crib, WiFi

1BR in Prime Hyde Park Apt

The price is CA $131
CA $285 total
includes taxes & fees
Aug 25 - Aug 26
1BR in Prime Hyde Park Apt
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Lobby

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is CA $151
CA $197 total
includes taxes & fees
Aug 31 - Sep 1
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed
Relax & Unwind in This Comfortable 3BR Unit
Interior

Relax & Unwind in This Comfortable 3BR Unit

10.0 out of 10, Exceptional, (4)
"Lakeia was very accommodating throughout our stay."
The price is CA $218
CA $470 total
includes taxes & fees
Sep 3 - Sep 4
Relax & Unwind in This Comfortable 3BR Unit
Contemporary 2BR Apartment in Vibrant Hyde Park
Fridge, microwave, oven, stovetop

Contemporary 2BR Apartment in Vibrant Hyde Park

The price is CA $231
CA $432 total
includes taxes & fees
Sep 16 - Sep 17
Contemporary 2BR Apartment in Vibrant Hyde Park
Studio Apt Comfy & Sunlit
Fridge, microwave, oven, stovetop

Studio Apt Comfy & Sunlit

The price is CA $127
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Studio Apt Comfy & Sunlit
Furnished 3BR Apt w/ Laundry
3 bedrooms, iron/ironing board, WiFi, bed sheets

Furnished 3BR Apt w/ Laundry

10.0 out of 10, Exceptional, (2)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
The price is CA $183
CA $402 total
includes taxes & fees
Sep 2 - Sep 3
Furnished 3BR Apt w/ Laundry
Hyde Park 1BR w/ Charm
1 bedroom, iron/ironing board, travel crib, WiFi

Hyde Park 1BR w/ Charm

The price is CA $127
CA $285 total
includes taxes & fees
Sep 3 - Sep 4
Hyde Park 1BR w/ Charm
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior detail

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $198
CA $276 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is CA $245
CA $551 total
includes taxes & fees
Aug 25 - Aug 26
Cozy house in the city
Honeycomb Hideout w/ 2 bedrooms
Fridge, microwave, oven, stovetop

Honeycomb Hideout w/ 2 bedrooms

The price is CA $180
CA $583 total
includes taxes & fees
Aug 25 - Aug 26
Honeycomb Hideout w/ 2 bedrooms
Cozy Room with Rooftop Lounge & City Views in River North
Property grounds

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is CA $215
CA $318 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Room with Rooftop Lounge & City Views in River North
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is CA $144
CA $303 total
includes taxes & fees
Sep 2 - Sep 3
The One: A 1BR Stay That Feels Like Home
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (4)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1BR in West Loop
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is CA $104
CA $397 total
includes taxes & fees
Aug 25 - Aug 26
Getaway Near ORD With Great Local Amenities
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is CA $148
CA $308 total
includes taxes & fees
Sep 2 - Sep 3
Sun-Drenched 1BR Apartment
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4
TV

Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

10.0 out of 10, Exceptional, (2)
"We liked the location and all of the amenities. "
The price is CA $324
CA $607 total
includes taxes & fees
Aug 25 - Aug 26
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4
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

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Great hotel in the heart of Chinatown. One block from the El and easy to get anywhere."
Dawn 3-night trip
Posted 1 day ago
Jaslin Hotel