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Search Vacation Homes in South Suburbs

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

Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Living Room / Dining Room with Fully stocked kitchen
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
9.8 out of 10, Exceptional, (10)
"This property was great. It’s close enough to the bus and train that you can get anywhere in less than 20 minutes usually but far enough out that you feel like you get a break from everything. The property is clean and everything works well. If you plan on cooking you may want to bring some of your own kitchen gear. We found ourselves without hot pads for a dinner we baked and a spatula for pancakes. We very much enjoyed our time and would recommend this place (and host) to anyone. "
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
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 4 br Old Town Home; Private Yard; Parking; Amazing Location
Room
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.8 out of 10, Exceptional, (77)
"Property was clean, manager was very easy to communicate with, lots of spacious beds / bathrooms, parking was easy and kitchen and living space included everything we needed. Location near Wells Street, North Avenue, Lakefront and Brown Line was perfect. Everything was easily walkable. This was a great house in the middle of a nice neighborhood for a large group."
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Luxury SOHO Styled Two-Level Townhouse - Old Town
Luxury SOHO Styled Two-Level Townhouse - Old Town
10.0 out of 10, Exceptional, (10)
"We had a great stay at this property. It is walking distance from everything you need in old town but also safe, quiet, and secure! Would highly recommend to other groups looking for a weekend in Old Town Chicago!"
Luxury SOHO Styled Two-Level Townhouse - Old Town
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
9.0 out of 10, Wonderful, (7)
"It was great experience! Check in and check out was very easy, and the room felt so much bigger than the photos so thats great. The parking though gets a bit tricky due to how tight it was but it shouldnt be a problem for most of us! Overall an awesome experience, very fast responses from the owner, and very friendly."
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Luxury Home Away From Your Home
Exterior
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (114)
"Definitely gently used but was comfortable. Ms. Linnie, the host, is very responsive and accommodating. Was missing hair dryers and flat sheets on beds but did not negatively affect our visit."
Luxury Home Away From Your Home
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
8.2 out of 10, Very Good, (34)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.2 out of 10, Wonderful, (14)
"Great location large unit. Still a bit under construction"
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Living area
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (28)
"Back to Chicago with a group for a work trip and of course we went back to the place we stayed at last time. Once you find a gem like this one, you stay with it! They keep this place with all the amenities you’d have at home. It’s incredibly spacious and the parking spots make it deal for a group. We’ll be back!! Jon"
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Oak Park, IL, entire house, short walk to train.
Living area
Oak Park, IL, entire house, short walk to train.
9.4 out of 10, Exceptional, (19)
"Great host communicates well if you need him. Helped with all my concerns. Check in was was easy and smooth. Property inside and out was also clean and in a nice neighborhood with access to ALOT. Thank you"
Oak Park, IL, entire house, short walk to train.
Cozy Home Sweet Homewood.
Interior
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (11)
"Great and quiet location. Comfortable very clean neat enough space for us . We greatly recommend hopefully we able to stay next year. Nice backyard "
Cozy Home Sweet Homewood.
Cozy 3-bedroom home on the waterfront, dog friendly!
Family room & kitchen
Cozy 3-bedroom home on the waterfront, dog friendly!
10.0 out of 10, Exceptional, (22)
"We love this space so much that it’s our second time staying here. Right on the river, isolated and private with just one house next door and very very peaceful. Took the dog and he swam from sun up to sun down. Just be careful when the river starts to flow, it is fast. But even just sitting on the dock watching him swim was enough for us. Already planning a trip next."
Cozy 3-bedroom home on the waterfront, dog friendly!
Stunning Condo #2 - Downtown River North!!!
Stunning Condo #2 - Downtown River North!!!
9.4 out of 10, Exceptional, (10)
"Looks just like the pictures, the house was very clean and decorated so cute! The host was very easy to get in touch with if needed. Amazing stay!! "
Stunning Condo #2 - Downtown River North!!!
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 BR / 3.5 BA Newly Built Home in Logan Square!
Private kitchen
5 BR / 3.5 BA Newly Built Home in Logan Square!
7.6 out of 10, Good, (7)
"We had a minor hiccup in the beginning and Sandy got it taken care of within an Hour. Overall great stay"
5 BR / 3.5 BA Newly Built Home in Logan Square!
Stunning Duplex Condo #1 - Downtown River North
Living Room / Dining Room combo with Fully Stocked Kitchen
Stunning Duplex Condo #1 - Downtown River North
9.8 out of 10, Exceptional, (9)
"We had an amazing trip to Chicago and loved staying at this condo. It was clean, modern, and a short walk/Uber ride to everything we wanted to see. The primary shower was AMAZING and we all felt safe with the double locks on the entryway and unit itself. Highly recommend staying here!!!"
Stunning Duplex Condo #1 - Downtown River North
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Private kitchen
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.2 out of 10, Wonderful, (49)
"A beautiful apartment in a perfect location. Walking distance to Wells street in old town. The apartment itself was very comfortable and had everything we needed. The host also was very helpful with everything "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Immaculate Brand New Penthouse Chicago!
Living Room - 1
Immaculate Brand New Penthouse Chicago!
9.4 out of 10, Exceptional, (8)
"This was such a convenient and overall great stay. There is plenty of room for everyone to sleep comfortably and check in/out was super easy. Definitely recommend this for large groups or families. Would stay here again! "
Immaculate Brand New Penthouse Chicago!
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, (28)
"Walking distance to Marquette Beach ($10 daily parking) or a 10-minute drive from the more popular West Beach (the westernmost part of the National Park, $25 daily parking). The house was comfortable, and we enjoyed grilling and using the hot tub in the backyard. Note: The Wi-Fi doesn't work well, and you'll need to bring your own coffee for the coffee machine (or use the Keurig)."
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Suite 1 on Southport 4 Queen Beds!
Living Room / Fully stocked kitchen
Suite 1 on Southport 4 Queen Beds!
10.0 out of 10, Exceptional, (8)
"Great location and very nice house"
Suite 1 on Southport 4 Queen Beds!
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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.
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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, (540)
"I’ll start by saying that I travel frequently…all over the world and Im super flexible with taking things in stride when something goes awry, but the parking situation was enough for me to want to cancel my stay. It was a nightmare and cost me more than I ever imagined paying for parking and the inconvenience that came with it. Never again! The apartment was nice, even if over priced, but I get it’s Chicago and the location is good. The staff was helpful by phone in the days leading up to my...
The price is AED 658
AED 880 total
includes taxes & fees
30 Sep - 1 Oct
Sentral Michigan Avenue
Sonder South Wabash
Interior
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (370)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is AED 747
AED 877 total
includes taxes & fees
9 Oct - 10 Oct
Sonder South Wabash
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (155)
"Loved staying there . Super clean and quiet as far as neighborhood. I would point out the wall may be a little thin, you can “ hear your neighbor sneeze or talk” pretty clearly . I’m just pointing it out if you are sensitive to noise. Other than than, a lovely place to stay."
The price is AED 562
AED 660 total
includes taxes & fees
2 Oct - 3 Oct
Sonder Market Hall
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.