South Side Holiday Rentals

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Holiday Rentals in South Side

LakeHouse
10.0 out of 10, Exceptional, (7)
"Great"
LakeHouse
cozy home in Bridgeport Chicago. walking to park and river front
10.0 out of 10, Exceptional, (1)
"Staying at this VRBO house in Chicago was an absolute knockout! The location was perfect for catching the wrestling show with my friends, and the house itself was spacious, clean, and had all the amenities we needed. From comfy beds to a fully equipped kitchen, we felt right at home. The host was super accommodating and made check-in a breeze. Definitely a five-star experience – would book again in a heartbeat!"
cozy home in Bridgeport Chicago. walking to park and river front
Cheerful 4 bedroom smart home w/ indoor fireplace
7.4 out of 10, Good, (6)
"The check in process was great and the house was very clean. It was easy to communicate with the property manager. Helped make our trip to chicago great!"
Cheerful 4 bedroom smart home w/ indoor fireplace
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Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (60)
"The location is perfect for plans to the museums and easy access to Lake Shore Drive. It also has plenty of street parking."
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (426)
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is NZ$387
per night
1 Jul - 2 Jul
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (94)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is NZ$163
per night
30 Jun - 1 Jul
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (309)
"Sonder rocks!"
The price is NZ$372
per night
2 Jul - 3 Jul
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (249)
"Parking should be available at a discounted rate. Not free, but in and out privileges at the least would stay agin, if I did not need to travel all over Chicago"
Kasa Magnificent Mile Chicago
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (131)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$314
per night
4 Jul - 5 Jul
Found Chicago powered by Sonder
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (212)
"Loved all the neighborhood dogs & farmers market"
The price is NZ$538
per night
16 Jun - 17 Jun
Level Chicago – Old Town
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (77)
"Small studio with queen bed and good kitchen facilities. Design very basic / post-industrial (with exposed pipes and wires)."
The price is NZ$472
per night
4 Jul - 5 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (34)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
The price is NZ$553
per night
18 Jun - 19 Jun
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (107)
"Loved it "
The price is NZ$423
per night
18 Jun - 19 Jun
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (188)
"Very nice property "
The price is NZ$154
per night
9 Jun - 10 Jun
WoodSpring Suites Chicago Addison
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$372
per night
2 Jul - 3 Jul
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (39)
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
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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.

Other types of properties in South Side you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6853)
"Good location but very noisy"
The price is NZ$282
per night
16 Jun - 17 Jun
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2956)
"Staff was super nice and the location was perfect. I was unaware of how small the room/beds would be and wish it could have been communicated better considering we had 4 people..but overall had a great stay"
The price is NZ$275
per night
7 Jul - 8 Jul
River Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very good, (2365)
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay again."
The price is NZ$399
per night
7 Jul - 8 Jul
Embassy Suites by Hilton Chicago Downtown River North
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our South Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up South Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in South Side. Seeing all the best attractions is bound to make you fall in love with South Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in South Side short-term rentals, that won’t be hard to do.

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