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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

Compare 334 Vacation Homes in South Side with updated reviews, rates, and availability.

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (86)
"Location of house is great, communication with owner is great. The house "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Eddy House, Roscoe Village Hideaway
Fridge, microwave, oven, stovetop

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway
Your Next Vacation Home
Private kitchen

Your Next Vacation Home

9.8 out of 10, Exceptional, (31)
"It was great! close to a lot. "
The price is ￥22,430
￥41,986 total
includes taxes & fees
Mar 2 - Mar 3
Your Next Vacation Home
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Fridge, microwave, oven, stovetop

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Spacious open concept home w/ game room + firepit
Microwave, dishwasher, coffee/tea maker, toaster

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (52)
"This property was in a great location! Easy to find and central to make getting to the surrounding cities super easy. The property was easy to access, which was my number one worry, and we had a fantastic time with our stay. Thank you, Amanda!"
Spacious open concept home w/ game room + firepit
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Fridge, microwave, oven, stovetop

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Fridge, microwave, oven, stovetop

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (39)
"We stayed here in January to visit some family and enjoy the city. The location of this place is amazing. its right downtown , very walkable to everything. The parking is great, with the 2 car garage it was heaven for being in the city. The property is so nice. Its massive. upstairs and downstairs ; with room for so many people. We ended up only have four people ; and just loved it. The living room is so cozy, with the fireplace and sofas, the property was perfect. Matches all the...
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Private kitchen

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Exterior

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

9.6 out of 10, Exceptional, (7)
"Stayed here for a week while attending a festival and central downtown location was good. Having the garage was very helpful but suggest you have a small car as the garages are very shallow. Common area with kitchen and TV is very spacious for lounging"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Cheery 2+bedroom home with free parking on premises
Fridge, microwave, oven, stovetop

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises
Berwyn Beauty
Fridge, microwave, oven, stovetop

Berwyn Beauty

10.0 out of 10, Exceptional, (13)
"Amazing... location, price, amenities, etc."
Berwyn Beauty
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
Terrace/patio

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Microwave, oven, stovetop, dishwasher

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Stunning / Spacious 6BD Home + garage - Bucktown!
Fridge, microwave, oven, stovetop

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...
Stunning / Spacious 6BD Home + garage - Bucktown!
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Fridge, microwave, oven, stovetop

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (38)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Interior

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (123)
"Spacious inside, 9 bedrooms, very warm in a cold month. Good location to walk, close to public transit and ample parking - squeezed in 5 vehicles. Owner contact and responses excellent."
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Fridge, microwave, oven, stovetop

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (46)
"The home was updated and very clean. The kitchen was large and was well stocked. The owner provided everything you would need to cook. The fenced in yard was a bonus as we traveled with our dog. The neighborhood is older and safe. The neighboring homes are well maintained. The street in front of the house is busy during rush hour, but didn't create an issue pulling out into traffic. We did not experience noise from the traffic. We had one small glitch which was taken care of quickly. The...
The price is ￥24,224
￥52,859 total
includes taxes & fees
Mar 18 - Mar 19
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Aerial view

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Interior

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
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 Side

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Smart TV

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.6 out of 10, Exceptional, (69)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
The Vibe Headquarters
Living area

The Vibe Headquarters

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very clean and cozy! Home away from home!"
The Vibe Headquarters
Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (681)
"This is a great hotel. The rooms have a kitchenette and the staff is wonderful! Beautiful hotel, great amenities. "
The price is ￥16,396
￥23,636 total
includes taxes & fees
Feb 24 - Feb 25
Sentral Michigan Avenue
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.