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Search Vacation Homes in South Suburbs

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Vacation Homes in South Suburbs

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

7.4 out of 10, Good, (8)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is AED 569
AED 923 total
includes taxes & fees
8 Sep - 9 Sep
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is AED 221
AED 1,841 total
includes taxes & fees
23 Sep - 24 Sep
4BR Retreat w/ Theater, Game Room & Backyard
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (53)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square
Chic and Spacious Bi-level 3BD in Bucktown!
Microwave, toaster, cookware/dishes/utensils

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!
Belmont House, Classy & Chic/walk to Wrigley Field
Interior

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (50)
"Great bang for your buck. Great area and great communication "
Belmont House, Classy & Chic/walk to Wrigley Field
A Home Away From Home!
Smart TV, fireplace

A Home Away From Home!

9.6 out of 10, Exceptional, (9)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!
Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

7.0 out of 10, Good, (11)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Feel good, live well in this cozy Wheaton 3 bedroom!
Living area

Feel good, live well in this cozy Wheaton 3 bedroom!

10.0 out of 10, Exceptional, (1)
"Very clean. Spacious, open living area, lots of storage and comfortable beds. "
Feel good, live well in this cozy Wheaton 3 bedroom!
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (14)
"This duplex in Old Town was very tastefully refurbished and decorated. The kitchen is outfitted with the best appliances, including an electric kettle. (Note to hosts: ALWAYS provide a tea kettle of some kind and you'll get an automatic five-star rating from me!) The house is quite roomy and comfortable and the four of us settled in nicely. It's a bit of a walk to the train, but the neighborhood is nice, so you don't mind. I highly recommend."
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Wrigley Field/Lakeview -Entire Home- Large Groups!
Fridge, microwave, oven, stovetop

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (83)
"This was the perfect stay for our family while we were in town for our daughter's graduation. The house was plenty big to accommodate our group, and the location is excellent. The host was very accommodating and easy to get in touch with. It was one of our best VRBO experiences yet."
Wrigley Field/Lakeview -Entire Home- Large Groups!
Miller Beach Blue Door By The Shore #2
Beach

Miller Beach Blue Door By The Shore #2

7.0 out of 10, Good, (12)
"Perfect!"
Miller Beach Blue Door By The Shore #2
Luxury House in the heart of Old Town with Parking
Interior

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
Fridge, microwave, oven, stovetop

Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

10.0 out of 10, Exceptional, (17)
"This was such a nice place in a great location. Really clean, comfortable, everything we needed. I would stay here again. Thank you!"
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!
Desk, iron/ironing board, free WiFi, bed sheets

Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
TV

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

9.6 out of 10, Exceptional, (170)
"Great space! Great location! "
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Exterior

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

9.8 out of 10, Exceptional, (26)
"Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay."
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Smart TV, fireplace, foosball

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

2.0 star property
10.0 out of 10, Exceptional, (13)
"This was a central location for us to meet with friends, nice accommodations, and a little bit of everything nearby.Hostess was so kind and helpful; house was great and fun for a relaxing weekend from space, to a large fenced backyard to the fire pit. Great place!"
The price is AED 900
AED 1,987 total
includes taxes & fees
5 Sep - 6 Sep
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Fridge, microwave, oven, stovetop

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (10)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Cozy Full Home + Free Parking + Fast Wi-fi & Central Area
Living area

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area
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 Suburbs Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Incredibly helpful and personable staff. Comfortable, clean, well kept room. "
Laurel Elizabeth 1-night trip
Posted 1 day ago
Hilton Chicago

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Explore a world of travel with Expedia