Search Vacation Homes in South Side

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Compare Vacation Homes in South Side with updated reviews, rates, and availability.

Lincoln Park Living - Suite 1
10.0 out of 10, Exceptional, (3)
"Spacious, very clean, and comfortable. It is located on a busy street, but the property is not facing the street. So it was not noisy. It had the convenience of public transportation. We did not use the kitchen very much, but it was a full kitchen. We enjoyed our stay and would recommend it to others."
Lincoln Park Living - Suite 1
Stunning Duplex Condo #1 - Downtown River North
10.0 out of 10, Exceptional, (2)
"This location was incredible and it was perfect for what we needed to do. We were in town for NEOCON/Design Days and this was a wonderful home base for us. It was walking distance to almost everything, and right by the CTA station as well. Starbucks was also close which was nice."
Stunning Duplex Condo #1 - Downtown River North
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
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Beautiful, Remodeled Penthouse Unit in Old Town!
9.0 out of 10, Wonderful, (8)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (5)
"This was exactly what we were looking for! Great location and will stay anytime I’m in Chicago!"
Luxury Downtown Penthouse with Private Rooftop!
national historic home near downtown airports no parties no events
9.0 out of 10, Wonderful, (21)
"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"
The price is ¥47,220
per night
Jun 17 - Jun 18
national historic home near downtown airports no parties no events
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (4)
"The unit was a great size for our 7-person group trip to Chicago. We’ll appointed with pulsated hardware and decor. Super close to transit made getting to Wrigley, Navy Pier, Downtown, and the zoo extremely easy. Rooftop was a amazing and Dan was responsive and made the check in/out process a breeze."
Breathtaking Downtown Penthouse B - Sleeps 11
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, (30)
"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"
The price is ¥19,990
per night
Jul 3 - Jul 4
Dunes Escape - Minutes from Indiana Dunes National Park
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is ¥25,814
per night
Jul 3 - Jul 4
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Brownstone in Gold Coast - Downtown
9.8 out of 10, Exceptional, (10)
"Enjoyed the location of the unit, easy to see much of the city. Check in process was easy."
Brownstone in Gold Coast - Downtown
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (5)
"Visit Chicago for my daughter's college graduation, and this place was perfect for my family to stay and enjoy the area and able to attend our events along with many choices of eating places."
Lincoln Park Living - Suite 2!
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, (2)
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is ¥31,323
per night
Jun 30 - Jul 1
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, (9)
"The ceilings are tall and space is welcoming. The tile in the shower was really cool and the towels were perfect. It was nice to have an open kitchen available but I did not need it as the food in the neighborhood was so yummy. The bed was awesome and the pillow was incredible. To top it off a client came over and we played pool. Another thing I enjoyed was the shoes at the door policy… clean spaces start with no shoes and this place is clean and stylish. Great location and I am happy to give...
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Your Next Vacation Home
10.0 out of 10, Exceptional, (11)
"Our stay was perfect for the few days we stayed for my niece's wedding. We enjoyed the house and its accommodations. Our host, Pervaiz was wonderful as well. I will definitely come back and refer my friends and family. Thank you, Jeanette!!"
The price is ¥36,989
per night
Jul 1 - Jul 2
Your Next Vacation Home
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (72)
"Perfect house for a large group! There are plenty of beds and bathrooms. The location is awesome. The host was super attentive and checked in frequently without being annoying. We had an awesome time!"
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Cozy Gary Vacation Rental: Steps to Beach!
9.4 out of 10, Exceptional, (22)
"We spent a wonderful long weekend in this charming cottage, had perfect weather for our multiple outings to the beach, which is steps away as advertised! The cottage was very well equipped with everything we needed, and the neighborhood is outstanding! We will definitely be back!"
Cozy Gary Vacation Rental: Steps to Beach!
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (4)
"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."
Cozy Home Sweet Homewood.
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (72)
"Stayed with 10 friends for the weekend. Clean unit with plenty of beds. Listing and pictures are accurate. Great location close to bars, restaurants, and train stop. Property manager was very responsive. Very easy check-in/check-out."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
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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 property types 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
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
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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