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Vacation rentals with a patio in South Loop, Chicago

Find and book unique accommodations with an outdoor patio on Airbnb

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Popular amenities for South Loop, Chicago accommodations with an outdoor patio

Apartment rentals with a patio

Superhost
Apartment in Chicago
4.87 out of 5 average rating, 105 reviews

Lovely 2-bedroom apartment in Pilsen

AnaRating, 5 stars2 weeks ago
Buena locación y dentro de un vecindario tranquilo
Guest favourite
Apartment in Edgewater
4.94 out of 5 average rating, 69 reviews

Spacious! 3 bedroom apartment in Edgewater!

PatrickRating, 5 stars1 month ago
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.
Guest favourite
Apartment in Hyde Park
4.92 out of 5 average rating, 102 reviews

Spacious 1BR Garden Apt & Parking

TomásRating, 5 stars1 week ago
Mikael's place was amazing. Unlike most places listed around Hydde Park in Chicago, Mikael's place had from great reviews and they were totally right. The place is very well kept, spacious, practical, with very calm surroundings. I had great sleep and having breakfast while looking at the garden was a big plus for me too. I had no issues regarding privacy or noise which is something commonly brought up in listings in this sector, especially in old buildings. Mikael was also very responsive and kind. If I ever go back to Chicago I would definitely consider staying here again.
Guest favourite
Apartment in Avondale
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

ÁlvaroRating, 5 stars1 month ago
El apartmento es cómodo, muy limpió y amplio para 4 personas. La zona nos pareció agradable y tranquila. Además está bien conectada, la estación de metro está cerquísima. Lo único que no nos gustó es no poder regular nosotros el termostato de la calefacción.
Top guest favourite
Apartment in Uptown
4.98 out of 5 average rating, 40 reviews

2 Room Apartment in Vintage Bldg

AudréanneRating, 5 stars1 week ago
We loved the apartment. It is ideally situated and was perfect for our little dog. The area is really nice an peaceful. It was also easy to get downtown via the red line. Karen was a fantastic host. We appreciated all the little gestures and the fact that she had saved a parking spot for us upon our arrival. We would come back anytime.
Superhost
Apartment in Glenview
4.86 out of 5 average rating, 28 reviews

1 Bedroom Apartment/free parking

DarrenRating, 5 stars1 month ago
We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!
Guest favourite
Apartment in Edgewater
4.95 out of 5 average rating, 21 reviews

Tree-Lined Street Near the Lake!

KarenRating, 5 stars1 month ago
This place has the best location. It was easy for me to take the Brown line and get around town. Cute coffee shop bakery on the corner. Mark and Carmen where friendly when we meet in the garden. Nice stay!
Top guest favourite
Apartment in Edgewater
5 out of 5 average rating, 25 reviews

Garden Apartment- RickStan Manor

AngeloRating, 5 stars1 week ago
Places is great. Easy access to train that can take you downtown, Lord of restaurants, supermarket and pharmacy around on a very peaceful neighborhood. Stanley was great host all around and house was awesome. Highly recommended

House rentals with an outdoor patio

Superhost
Home in Berwyn
4.9 out of 5 average rating, 31 reviews

European Custom Built Home

DanRating, 5 stars1 month ago
the home was fantastic. it fit our need perfectly! thank you for a fantastic stay.
Superhost
Home in West Lawn
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Superhost
Home in Illinois Medical District
4.86 out of 5 average rating, 101 reviews

Casa PLZN Location | Entire Home | Garage Parking

RicardoRating, 5 stars2 weeks ago
Great place! I’ll definitely be coming back! The beds are amazing!
Top guest favourite
Home in Worth
5 out of 5 average rating, 16 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

SawsanRating, 5 stars1 month ago
Amazing house and location. Great host. Highly recommend.
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Superhost
Home in Des Plaines
4.85 out of 5 average rating, 101 reviews

Cozy Home by O'Hare + EV Plug

SocorroRating, 5 stars2 days ago
Me and my family enjoyed our stay especially the birthday girl so thank you for making her birthday special. ❤️
Top guest favourite
Home in Chicago Ridge
4.94 out of 5 average rating, 124 reviews

Quiet cul-de-sac with huge fenced in backyard

JazzmenRating, 5 stars3 weeks ago
Tom and his dog Bear... were great!! Beautiful home and great area. A lot of places that we wanted to go to were close by will definitely come again. Thank for having such a welcoming home.
Top guest favourite
Home in Beverly
4.9 out of 5 average rating, 39 reviews

Suburban Feel with a City Vibe

IngessonRating, 5 stars2 days ago
I am very happy to have rented for the holidays it is really beautiful Very clean quiet area

Condo rentals with a patio

Superhost
Condo in Wicker Park
4.84 out of 5 average rating, 184 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

KathyRating, 5 stars1 month ago
Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.
Guest favourite
Condo in Bridgeport
4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars2 weeks ago
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend
Guest favourite
Condo in West Town
4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SearaRating, 5 stars2 weeks ago
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!
Guest favourite
Condo in Pilsen Historic District
4.93 out of 5 average rating, 118 reviews

Urban Oasis | Great for Families w/ Kids

ParkerRating, 5 stars2 weeks ago
We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!
Superhost
Condo in Logan Square
4.79 out of 5 average rating, 251 reviews

Logan Square Beauty with 2 Bedrooms W/parking

SarahRating, 5 stars1 week ago
We really enjoyed our three nights in Matt's roomy upstairs apartment. Great to have a space in his garage; the car stayed parked there while we took the blue line downtown each day. It was an easy 10 minute walk to the Logan Square station. If you're flying into or out of O'Hare, it would be convenient, since the airport is the last stop on the blue line.
Guest favourite
Condo in Lincoln Park
4.91 out of 5 average rating, 102 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KathleenRating, 5 stars5 days ago
It was exactly as it was pictured except the front door is adjacent to a beauty salon and a bit hidden at first. The place was immaculate - very clean and the kitchen in particular was excellently appointed. It is on the third floor in an older building so there are stairs. The building was quiet. With gated and lit parking provided nearby our vehicle was safe.
Top guest favourite
Condo in Lake View
4.98 out of 5 average rating, 116 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

AndrewRating, 5 stars1 week ago
Under the category of actions speak louder than words, I have stayed at Allan's place about five times, and it remains my first choice when visiting Chicago.
Superhost
Condo in Near West Side
4.86 out of 5 average rating, 145 reviews

Tri-Taylor/Medical Dist. near West Loop

MelindaRating, 5 stars3 weeks ago
We had a great time in your space. We had everything we needed!

Quick stats about vacation rentals with a patio in South Loop, Chicago

  • Total rentals

    190 properties

  • Nightly prices starting at

    $41 CAD before taxes and fees

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

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  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Loop
  7. Rentals with a patio