
Vacation rentals with a patio in South Side
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Top-rated patio rentals in South Side
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Apartment 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.

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.

3 Bed 3 Bath Lakefront Oasis, Parking Included
Great stay. The property is tucked away and is away from all the city noise. It was very clean and everyone was really impressed. Thank you Sally for a great stay.

Home in Forest Park Upstairs.
He was available without delay and really seemed like a kind person. The location is wonderful whether you're looking for safe and simple stay or a trip into city. Highly recommend!

The Green Bungalow: Charming 1-BR apt. with patio
We decided to book this space for a last-minute birthday getaway. It was very clean, had a charming historic feel, and was conveniently located just a short drive from all the best spots. I would book again!

Logan’s Cozy Inn.
Great location with lots of nice bars and restaurants locally and easy access also to the CTA blue line to Downtown and O’Hare. Apartment was ideal and was just as described. Would recommend and if ever back in Chicago would look to stay here again.

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!

Lux_Home Chicago 8 mins Downtown
I had a great experience staying at this Airbnb! The place was clean, cozy, and just as described in the listing. The host was very responsive and made check-in super easy. I’d definitely stay here again.

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.

Garden Unit, King & Queen, Kitchenette & Parking
We stayed one night and were very happy with the accommodations. Lisa was a helpful host and everything was very nice quality and squeaky clean. The bed was super comfortable and the shower was very nice with a big “rain” type showerhead AND a regular size detachable one. The neighborhood and yard area was calm and chickens were very cute! We had some fantastic empanadas at a nearby cafe called La Mulata - definitely recommend. There are a bunch of cool historical buildings nearby too (including the building the cafe is in). FYI since it’s a basement apartment (as advertised) there are a couple spots with slightly lower beams coming down from the ceiling). At 6’2” we were good to walk around without impediment, but I put my hand above my head at the lowest spot and the clearance was only about an inch, so if you are any taller, be careful or you may hit your head! Excellent place - thanks Lisa :)

Exquisite Chicago Modern Rooftop, Sleeps 9
I love everything about this home and all the e amenities, and the private rooftop was the greatest touch of the property Vince was amazing and very easy to reach in very fast responding.Thanks so much .

Spacius unit in historic gem
Nyeri was very responsive and helpful throughout our stay and immediately dealt with any issues that came up. Her suggestions were spot on and she even provided a discount code to order food! The space was comfortable for the 5 of us, and allowed us to rest, visit with each other, and prepare meals. There is construction going on next door but we barely heard them. Thanks for a wonderful stay!
Condo rentals with a patio

Lovely top floor 2BR/2BA, steps from everything!
The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.

Urban Oasis | Great for Families w/ Kids
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

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
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

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!

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

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.
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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
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center