
Holiday rentals with a patio in South Side
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Top-rated rentals with patio in South Side
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Popular amenities for rentals with patio in South Side
Flat rentals with a patio

Lovely 2-bedroom apartment in Pilsen
Very quiet neighborhood, the house is an easy 7min walk to the pink line. Quick ride to Chicago downtown. There is a cute bakery within walkable distance as well as a few grocery stores within a mile. The place itself looked exactly like pictures, very clean.

Modern 3BR with Private Rooftop & Free Parking
Song’s place was perfect for our family trip to Chicago!

Al Capone Era Speakeasy 3 BR
For basics, it is very clean and comfortable with a well appointed kitchen, comfortable beds, and easy street parking. The space itself is remarkable. Patterned tin walls and ceilings, a triangular shape, nicely decorated, and the construction details from converting it to an apartment are all in keeping with the style. We loved it.

Cozy guest studio, great for couples!
Great place . Very nice and responsive host. Great for couples. Great location

Vibrant & Chic Apt On Quiet St in Andersonville
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.

Montrose Gardens
Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed

Spacious Haven Near Green Line, 20mins to Downtown
El alojamiento es tal cual aparece en las fotos, muy grande y cómodo. Llegamos un poco tarde y la zona de la estación del metro no es tan bonita, y un poco solo, sin embargo, la zona es muy central, acceso a bus, supermercado. Muy recomendado este alojamiento, nos gusto mucho.

Lovely Garden Studio Apartment.
Kasey and her husband were awesome host!!They were kind & responsive! My friend and I come during a time in winter and Kasey was very quick to keep us warm! Although they do have a child it was very rare when we were disruptive by noise! Love the vibes of the Airbnb and the fact that I felt like home says something! I definitely recommend staying here. Such a co beautiful and peaceful area as well.
House rentals with a patio

Modern Family Townhouse
Convenient to Hyde Park and the University of Chicago, the home was incredibly clean. I was a little worried since this is the hosts' primary home, but the kitchen was clutter-free, and the bedrooms had plenty of room for our personal items. It was also great to have a guaranteed parking spot in a gated area. The owner was proactively communicative, and everything was just as described. The rental easily fit our family of five. Would definitely stay here again!

Family Friendly Duplex/9 min from MDW/Free Parking
Very comfortable place and nice and very responsive host! Definitely recommend this stay!

Division St Designer Home In Heart of Wicker Park
I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!

Animal House near Sox stadium
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

Unique porcelain-enamel paneled "Lustron" home
We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=

Floresitas Oasis, your home in Chicago
Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!

Private Logan Square Garden Apt
Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

Steps from the beach and a mile from National Park
>Loved the meticulous attention given to cleanliness and the Award Worthy Décor. >The apparent attention to detail and thought given to enhance comfort. >The Clear available directions and Immediate responsiveness to concerns regarding technical issues was unparalleled. > Wish I could've stayed longer! Absolutely Heavenly!!
Apartment rentals with a patio

Urban Oasis | Great for Families w/ Kids
Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT
Excellent séjour en famille chez Cory. Il a été toujours très réactif à nos interrogations. Logement spacieux , confortable. Il été agréable de s’y reposer le soir après de longues marches dans Chicago. Nous recommandons vivement.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
I was coming to Chicago to just have a quiet weekend away from work and the stresses of home. I wanted a few days to enjoy urban life peacefully doing a few things I enjoy. This spot checked off all the boxes for peaceful and private but also re adorably we'll located to hit all of the spots around Chicago. The place was exactly as pictured and clean. couldn't have been easier and I would stay here again. hosts were responsive. it was a great few days.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
This was a fabulous place to stay! My brother and I could easily walk to the "L" and head downtown. The pizza place right downstairs was delicious - we ate there twice in three days! The beds were comfortable, the couch and living room set up was cozy. I would absolutely stay there again!

Tri-Taylor/Medical Dist. near West Loop
Great stay! The place was clean, comfortable, and in a convenient location. The host was friendly and helpful. I’d definitely stay here again!

Modern Chicago Movie Themed Apt
We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.

Wicker Park/Bucktown condo with large balcony
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center