Casas vacacionales en South Side

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Casas vacacionales en South Side: compara precios, opiniones y disponibilidad de 323 propiedades

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

10.0 de 10, Excepcional, (4)
“This is a very nice property in an up and coming neighborhood. The house is multilevel with three spacious bedrooms (two with ensuite bathrooms). As a bonus, the house has a garage opening onto an alleyway. Everything was very clean, bright and well appointed. The property is located in an up and coming neighborhood very convenient to good el lines and only a couple of blocks from a wonderful coffee place we used every day during our stay. Everything with the property went well and we would stay...
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Casa espaciosa en el casco antiguo: a pie de vida nocturna y Mag Mile; Estacionamiento para 3 autos

9.4 de 10, Excepcional, (81)
“Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! ”
Casa espaciosa en el casco antiguo: a pie de vida nocturna y Mag Mile; Estacionamiento para 3 autos

Hermosa mansión 9br con 5 espacios de estacionamiento. ¡Camina al campo de Wrigley y al lago Michigan!

10.0 de 10, Excepcional, (118)
“We were a group of 20 family members coming from all over the country for a wedding just a few blocks away. There was room for everyone, plus hairdryers, ironing board, iron, etc. needed to prepare for the big day. Target and Aldi, train station, and several coffee shops and restaurants, and parks within close walking distance made this the perfect location. Everyone loved staying here. We had good weather for porch sitting, and gathering outside after dark. Very helpful and available hosts too ...
Hermosa mansión 9br con 5 espacios de estacionamiento. ¡Camina al campo de Wrigley y al lago Michigan!

Cozy Home Sweet Homewood.

10.0 de 10, Excepcional, (15)
“We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.

Cheery 2+bedroom home with free parking on premises

9.8 de 10, Excepcional, (32)
“My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend.”
Cheery 2+bedroom home with free parking on premises

Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

9.6 de 10, Excepcional, (9)
“Stayed at the property for a conference at McCormick. Very convenient and nice.”
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 de 10, Excepcional, (9)
“Could not be more thankful for her prompt replies and accommodations.”
Nestled just behind Marquette Park. 5 minute walk to beach.

Desirable chic home in a Prime Location!

9.0 de 10, Magnífico, (2)
“My coworker and I stayed at this property for a work trip. The house was clean and modern, provided a bathroom for each of us, and was within walking distance of our company office in parkview plaza.”
Desirable chic home in a Prime Location!

LUXE 3 BR, 2 BA + Hot Tub

8.8 de 10, Excelente, (15)
“Older property which matched description well. Comfortably fit 5 adults and teens for 4 night stay. Quiet neighborhood even though it is right next to highway. Grocery store within a few mins. We traveled several times to downtown Chicago and Rosemont without issues (other than normal chicago traffic). There are stairs from any entrance, so just be prepared if you have a heavy cooler like we did. :) Could have been a bit cleaner, but that would not stop me from staying again. The host...
El precio actual es de MXN$5,620
MXN$9,572 en total
impuestos y cargos incluidos
3 dic. - 4 dic.
LUXE 3 BR, 2 BA + Hot Tub

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 de 10, Magnífico, (27)
“I invited 5 guest to join me in Chicago for a birthday trip. This home is perfectly located between MDW and ORD. We had no trouble getting to our activities, great restaurants, downtown, or quick stores (Target, CVS, etc). The layout of the home is perfect with rooms and bathrooms on each level. The homeowner is also a wonderful communicator, great at responding. We had no trouble getting a hold of them prior to the trip or during the trip. Highly recommend! ”
Stunning / Spacious 6BD Home + garage - Bucktown!

Monumento victoriano Inicio

9.8 de 10, Excepcional, (162)
“Very clean and well maintained. Would stay again for sure. ”
Monumento victoriano Inicio

Spacious open concept home w/ game room + firepit

9.8 de 10, Excepcional, (48)
“Our family of 4 had a wonderful stay here! Great neighborhood and a spacious home! The beds were super comfy & the home was decorated nicely! Thank you for having us Amanda! We’ll be back :) ”
Spacious open concept home w/ game room + firepit

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.2 de 10, Magnífico, (7)
“The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

10.0 de 10, Excepcional, (19)
“Beautiful, spacious, light-filled carraige house in a gorgeous historical neighborhood. Close to beach, shops, cafes. Janet was very accommodating and very hospitable. We loved it!”
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Discover Wheaton's charm.

9.8 de 10, Excepcional, (8)
“An exceptional place to stay. We felt very welcome. Plenty of room both indoors and out. Host is very responsive, respectful, and accommodating!”
Discover Wheaton's charm.

Casa de autocares Bucktown de 2 niveles y arbolada - Capacidad para 10

9.8 de 10, Excepcional, (21)
“Clean,an enjoyable experience! Lovely neighborhood with inviting bars and restaurants. Easy to navigate and close to everything. Bus and rail very accessible and affordable. We would book again. The combination of the 2 apartments was family friendly. We had a great time.”
Casa de autocares Bucktown de 2 niveles y arbolada - Capacidad para 10

Cozy 5-bedroom with lake views and spacious deck

10.0 de 10, Excepcional, (8)
“This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area.”
Cozy 5-bedroom with lake views and spacious deck

Luxury Suite in Glen Ellyn, IL USA

10.0 de 10, Excepcional, (5)
“The host was very communicative from the beginning. Had a bit of a booking hiccup via another site. Reached out to the host and she responded and rectified the situation right away. The unit is a split level, accessible only through the garage. We received the code to enter the door to the unit, well in advance. However, we did not receive the code to enter the garage until arrival (and after having to reach out to the host). Once again, the host was very quick to respond. The home is in a quiet...
Luxury Suite in Glen Ellyn, IL USA

Hermosa casa de pueblo de diseño ~ ¡Ubicación increíble! River West - 4 habitaciones

10.0 de 10, Excepcional, (87)
“The house was simply beautiful, and the hosts were very communicative and on top of things. Would stay here again”
Hermosa casa de pueblo de diseño ~ ¡Ubicación increíble! River West - 4 habitaciones

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.6 de 10, Excelente, (4)
“Overall it was a great experience and I’ll be coming back sooner”
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Precio más bajo por noche encontrado en las últimas 24 horas, con base en una estancia de 1 noche para 2 adultos. Los precios y la disponibilidad están sujetos a cambios. Aplican términos adicionales.
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Otros hospedajes en South Side

LakeHouse

10.0 de 10, Excepcional, (13)
“Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again ”
LakeHouse

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 de 10, Bueno, (12)
“Loved the place and host was super helpful when needed! ”
Cheerful 4 bedroom smart home w/ indoor fireplace

Espacioso nivel Bronzeville Brownstone Gdn cerca del centro y la Universidad de Chicago

9.8 de 10, Excepcional, (66)
“Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay”
Espacioso nivel Bronzeville Brownstone Gdn cerca del centro y la Universidad de Chicago
Precio más bajo por noche encontrado en las últimas 24 horas, con base en una estancia de 1 noche para 2 adultos. Los precios y la disponibilidad están sujetos a cambios. Aplican términos adicionales.
Vista hermosa de una playa con palmeras

Black Friday: 30% dto. o más a socios

Con el Black Friday, los socios ahorran 30% o más en hoteles seleccionados hasta el 4 dic. Hospédate antes del 15 dic. 2025.