South Side Holiday Rentals

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Check prices for these dates

Tonight
25 Jul - 26 Jul
Tomorrow
26 Jul - 27 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Holiday Rentals in South Side

Cheerful 4 bedroom smart home w/ indoor fireplace
Fridge, microwave, oven, stovetop

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (13)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace
The Chic Urban Oasis Near the Lake!
Overlooking the sandy beach and rocky shoreline, this property offers stunning views of the surrounding lush greenery and distant buildings.

The Chic Urban Oasis Near the Lake!

7.6 out of 10, Good, (5)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
Cozy Studio in Hyde Park-Walk to Lake & University
Compact kitchen with a stainless steel sink, gas stove, and ample countertop space.

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (1)
"The building in itself is very beautiful and serene and the apartment is very well kept, clean and has all the amenities one needs. The hosts are also incredible and just a txt away."
The price is HK$824
HK$1,584 total
includes taxes & fees
6 Aug - 7 Aug
Cozy Studio in Hyde Park-Walk to Lake & University
3BR Prime Hyde Park Location Near University of Chicago and Dining
Enjoy meals in this dining area with a long table for four, offering a view of the city and surrounding greenery.

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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
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
1 Mi to University of Chicago: Urban Escape!
Stunning historic building with a classic facade and symmetrical windows, set amidst a charming neighborhood.

1 Mi to University of Chicago: Urban Escape!

10.0 out of 10, Exceptional, (5)
"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
Relax in this stylish living room with a tufted sofa, framed artwork, and a coffee table.

Chic 1-bedroom apartment,15mims from downtown

10.0 out of 10, Exceptional, (1)
"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
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Kitchen features a refrigerator, microwave, stove, and sink, with a window and door.

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!
LakeHouse
Kitchen features dark cabinetry, stainless steel appliances, oven, and dishwasher.

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
Historic 3BR Retreat Near Univ of Chicago
Relax in this inviting living room with a comfortable sofa, glass coffee table, and cozy fireplace.

Historic 3BR Retreat Near Univ of Chicago

8.8 out of 10, Excellent, (5)
Historic 3BR Retreat Near Univ of Chicago
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Relax in this stylish living room with a sofa, coffee table, and dining area, perfect for unwinding.

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

2.5 star property
10.0 out of 10, Exceptional, (1)
"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.
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Classic residential building with a brick and stone facade, featuring a prominent entrance and large windows.

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
Cozy & Bright 1BR Apartment
Shower, hair dryer, towels

Cozy & Bright 1BR Apartment

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 HK$746
HK$1,497 total
includes taxes & fees
4 Aug - 5 Aug
Cozy & Bright 1BR Apartment
Stylish Hyde Park 1BR near UChicago
Relax in this inviting space with a leather armchair and tufted sofa, perfect for unwinding by the window.

Stylish Hyde Park 1BR near UChicago

2.0 out of 10, (1)
"I refused to sleep here. Dirty building, dangerous location, pictures are misleading."
The price is HK$738
HK$1,462 total
includes taxes & fees
27 Jul - 28 Jul
Stylish Hyde Park 1BR near UChicago
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Relax in this inviting living room with a large sofa, coffee table, and fireplace.

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
NEW Eco Stay by UChicago, Lakefront & Hyde Park!
Property grounds

NEW Eco Stay by UChicago, Lakefront & Hyde Park!

NEW Eco Stay by UChicago, Lakefront & Hyde Park!
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
9.8 out of 10, Exceptional, (7)
"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
Sleek 3BR Retreat: Hyde Park Comfort & Style
Relax in this inviting living area with a central island, sofa, and chair.

Sleek 3BR Retreat: Hyde Park Comfort & Style

9.0 out of 10, Wonderful, (2)
"If location is your priority--where you want to be in Hyde Park close to UChicago--then this property is an excellent choice. The property was perfectly clean and had some personal touches. But it seems as though the property has been newly furnished and newly outfitted, so it seems likely additional comforts and improvements will be forthcoming. For example, we thought there was no toilet paper as there was only a quarter of a roll left in the bathroom and no extra rolls stored in the bathroom;...
Sleek 3BR Retreat: Hyde Park Comfort & Style
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Cozy retreat with a large bed, dresser, and mirror, perfect for a restful stay.

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

8.8 out of 10, Excellent, (18)
"This is a very nice place to stay lo ation in convenient. Only issue is that its kinda noisy you can hear train and traffic. "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Stunning Victorian-style building with a corner turret, large windows, and ornate iron fence.

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.6 out of 10, Exceptional, (70)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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
"Great."
Arjun 4-night trip
Posted 3 hours ago
Hyatt Place Chicago-South/University Medical Center