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Search Vacation Homes in South Suburbs

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Compare 303 Vacation Homes in South Suburbs with updated reviews, rates, and availability.

Cozy Midway Home
Exterior detail
Cozy Midway Home
2.0 star property
10.0 out of 10, Exceptional, (12)
"This was a perfect little house to stay for our weekend trip! "
Cozy Midway Home
Lincoln Park Living - Suite 2!
Living Room / Dining Room
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (17)
"Very convenient. Spacious and comfortable condo."
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Interior
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (21)
"The property was perfect for me and my buddies for a football weekend!"
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Interior
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Terrace/patio
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (13)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
7.4 out of 10, Good, (3)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Interior
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Living area
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (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! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Casa Blanca in Miller Beach!
Exterior
Casa Blanca in Miller Beach!
9.8 out of 10, Exceptional, (65)
"The whole family enjoyed our stay and loved the location to the beach. We had a wonderful time."
Casa Blanca in Miller Beach!
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Room
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Spacious 5 BR / King Size Beds + Private Parking!
Living Room
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Table
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (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
Cozy Home Sweet Homewood.
Living area
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (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.
King Bed, DIsney+, Spacious, Family-Friendly House
Living Room
King Bed, DIsney+, Spacious, Family-Friendly House
10.0 out of 10, Exceptional, (20)
"I really enjoyed our stay at this location. It had good appliances and was very clean. Owners made it a point to communicate throughout! "
The price is AED 694
AED 1,366 total
includes taxes & fees
9 Dec - 10 Dec
King Bed, DIsney+, Spacious, Family-Friendly House
Pet-Friendly Lake Getaway: 1 Block to Beach!
Gary Vacation Rental | 3BR | 1.5BA | 1,600 Sq Ft | Stairs Required
Pet-Friendly Lake Getaway: 1 Block to Beach!
10.0 out of 10, Exceptional, (34)
"Property was very clean and photos accurate. Check in process was easy and we enjoyed a quick fall weekend get away to hike the Dunes. Good communication from owner. Thanks!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
Nestled just behind Marquette Park. 5 minute walk to beach.
Interior
Nestled just behind Marquette Park. 5 minute walk to beach.
10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
5 minutes from Midway Int'l Airport Single Family Home.
Family Room
5 minutes from Midway Int'l Airport Single Family Home.
9.2 out of 10, Wonderful, (5)
"Good area super easy process "
5 minutes from Midway Int'l Airport Single Family Home.
Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.2 out of 10, Wonderful, (17)
"So much fun! Dan was very communicative "
Beautiful, Remodeled Penthouse Unit in Old Town!
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
8.8 out of 10, Excellent, (33)
"We enjoyed our stay at Sandhill Flat. The check in process was easy and communication was clear. The place is spacious, clean and stocked well. I was impressed they provided some coffee and sugar packets. We enjoyed the spacious backyard, grill and hot tub in the evenings. We were close to the park and beach . We would return."
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Belmont House, Classy & Chic/walk to Wrigley Field
Interior
Belmont House, Classy & Chic/walk to Wrigley Field
9.4 out of 10, Exceptional, (41)
"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "
Belmont House, Classy & Chic/walk to Wrigley Field
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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Other property types in South Suburbs

Sentral Michigan Avenue
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is AED 396
AED 573 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (208)
"My stay at Sonder was an absolute delight! The property is very clean and the view and vibe was very cozy and perfect! The manager Jess went above and beyond helping out with questions and took great care of me! I will definitely be coming back! "
The price is AED 206
AED 242 total
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
Living area
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AED 443
AED 520 total
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
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.