South Side Vacation Rentals

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Check prices for these dates

Tonight
Aug 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
This weekend
Aug 15 - Aug 17
Next weekend
Aug 22 - Aug 24

Vacation Rentals in South Side

Come experience The Lake Shore!
Fridge, microwave, oven, stovetop

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (1)
"We had a great stay at the property. "
Come experience The Lake Shore!
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
Cozy Studio in Hyde Park-Walk to Lake & University
Microwave, oven, stovetop, coffee/tea maker

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is ￥14,040
￥29,326 total
includes taxes & fees
Aug 14 - Aug 15
Cozy Studio in Hyde Park-Walk to Lake & University
Perfect 1BR Spot near Attractions
Fridge, microwave, oven, stovetop

Perfect 1BR Spot near Attractions

7.4 out of 10, Good, (3)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
The price is ￥14,040
￥30,439 total
includes taxes & fees
Aug 18 - Aug 19
Perfect 1BR Spot near Attractions
3BR Prime Hyde Park Location Near University of Chicago and Dining
Dining

3BR Prime Hyde Park Location Near University of Chicago and Dining

2.0 star property
10.0 out of 10, Exceptional, (7)
"Excellent stay in a good location. The place is comfortable and big, the host was very kind and attentive. I hope to comeback soon. ☺️"
3BR Prime Hyde Park Location Near University of Chicago and Dining
1BR with Spacious Feel & Comfort
TV, offices

1BR with Spacious Feel & Comfort

5.0 out of 10, (2)
"This is exactly what we were looking for. Location is good near beautiful side streets and walking distance from shops and good restaurants. Very responsive host. Nice decorative touches and clean, efficient cooking area. Clean apartment which could use updating but if you want updates you’ll just have to pay more. This was our second stay in this general area and we liked this one better. Definitely a reasonable price for this area. Ad is accurate regarding the apartment. "
The price is ￥14,040
￥30,439 total
includes taxes & fees
Aug 17 - Aug 18
1BR with Spacious Feel & Comfort
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Smart TV, books

Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

2.5 star property
10.0 out of 10, Exceptional, (2)
"The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. "
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
1 Mi to University of Chicago: Urban Escape!
Exterior

1 Mi to University of Chicago: Urban Escape!

10.0 out of 10, Exceptional, (6)
"Quiet area. The owner was very welcoming and we had a very pleasant stay. Place was spacious and clean"
1 Mi to University of Chicago: Urban Escape!
Chic 1-bedroom apartment,15mims from downtown
Living area

Chic 1-bedroom apartment,15mims from downtown

9.0 out of 10, Wonderful, (2)
"Stayed here to work C2E2 for the weekend. Great big space with everything I needed to rest up after a long day of work."
Chic 1-bedroom apartment,15mims from downtown
1-bedroom condo next to Chicago Midway International Airport
Fridge, microwave, oven, stovetop

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (6)
"super nice place!"
1-bedroom condo next to Chicago Midway International Airport
Sleek & Functional 2-Bedroom Apt
Interior

Sleek & Functional 2-Bedroom Apt

10.0 out of 10, Exceptional, (1)
"Clean , awesome and nice apartment . Very close to the city and everything is around . Will stay again . Thank you "
The price is ￥14,483
￥34,269 total
includes taxes & fees
Aug 26 - Aug 27
Sleek & Functional 2-Bedroom Apt
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Microwave

Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

2.0 star property
9.6 out of 10, Exceptional, (9)
"Served us well for our event near the McCormick Center. Hospitality was second to none! "
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
Relax & Unwind in This Comfortable 3BR Unit
Interior

Relax & Unwind in This Comfortable 3BR Unit

10.0 out of 10, Exceptional, (3)
"Lakeia was very accommodating throughout our stay."
The price is ￥23,277
￥50,831 total
includes taxes & fees
Aug 25 - Aug 26
Relax & Unwind in This Comfortable 3BR Unit
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Exterior

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

8.0 out of 10, Very Good, (8)
"We enjoyed our stay, and the condo was perfect for my daughter and me. Great location, prompt responses to all communication with owner, super clean and very comfy beds! Main building corridor could use some sprucing up, but nothing major. Overall, very satisfied! Thanks, Khoy!"
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Fridge, microwave, oven, stovetop

The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!

2.0 star property
9.8 out of 10, Exceptional, (6)
"Spacious property, good location! Would stay again. Clean and quiet! "
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
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
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Smart TV

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

8.6 out of 10, Excellent, (7)
"My stay was very relaxing and amazing I really enjoyed when we arrived everything was clean the block that the property on was very quiet I will definitely stay here again if we needed anything Stephanie was on it I really appreciate your hospitality thank you "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Charming 3BR Chicago Apt in Prime Location
Fridge, microwave, oven, stovetop

Charming 3BR Chicago Apt in Prime Location

9.0 out of 10, Wonderful, (14)
"We truly enjoyed our stayed and will be back next month. The host/owner responds quickly to questions and is a great resource. The neighborhood is safe and many shops and restaurants are easily walkable. The only option is street parking but we did not have trouble finding a spot when needed. "
Charming 3BR Chicago Apt in Prime Location
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
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 ￥18,769
￥42,418 total
includes taxes & fees
Aug 19 - Aug 20
Furnished 3BR Apt w/ Laundry
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

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"I really enjoyed my stay here "
Anntonette Maria 5-night trip
Posted 1 day ago
Hyatt Place Chicago-South/University Medical Center