Holiday rentals with a patio in South Loop, Chicago

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Popular amenities for rentals with patio in South Loop, Chicago

Flat rentals with a patio

Superhost
Flat in Chicago
4.88 out of 5 average rating, 112 reviews

Lovely 2-bedroom apartment in Pilsen

BarboraRating, 5 stars1 week ago
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.
Guest favourite
Flat in Near North Side
4.92 out of 5 average rating, 142 reviews

Modern 3BR with Private Rooftop & Free Parking

JillRating, 5 stars1 week ago
Song’s place was perfect for our family trip to Chicago!
Superhost
Flat in West Town
4.79 out of 5 average rating, 48 reviews

Logan Square Oasis

MichaelRating, 5 stars6 months ago
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.
Superhost
Flat in Irving Park
4.79 out of 5 average rating, 141 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

AlysRating, 5 stars1 month ago
Carla's place was as described! Will book with this host again!
Guest favourite
Flat in East Rogers Park
4.8 out of 5 average rating, 10 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

NathanRating, 5 stars3 days ago
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.
Guest favourite
Flat in Irving Park
4.92 out of 5 average rating, 51 reviews

Montrose Gardens

AndrewRating, 5 stars1 week ago
Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed
Guest favourite
Flat in Logan Square
4.86 out of 5 average rating, 109 reviews

Logan’s Cozy Inn.

SandraRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Near West Side
4.98 out of 5 average rating, 107 reviews

Millennium park 10 min Free P-Spot&Balcony Sleep 8

BobbyRating, 5 stars2 weeks ago
Serg is an amazing host and his team for maintenance was extremely responsive. The area was close to Chicago and clearly undergoing gentrification but across the street from a firehouse which surprisingly was not loud at night or during the day. Great rooftop views and the apartment itself was spotless and magnificent. While not many high end restaurants due to being 5 minutes outside of the city. Great stay and great value.

House rentals with a patio

Guest favourite
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars3 weeks ago
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!
Guest favourite
Home in Bridgeport
4.96 out of 5 average rating, 122 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

LuciaRating, 5 stars2 weeks ago
We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.
Superhost
Home in Illinois Medical District
4.86 out of 5 average rating, 109 reviews

Casa PLZN Location | Entire Home | Garage Parking

AsiaRating, 5 stars4 days ago
We enjoyed our stay. The place is located in a convenient location close to many shops and restaurants and just around the corner from an L station. The home was very spacious and comfy for our short stay. You can hear the train in the house however it wasn’t bothersome even for our toddlers when they were asleep.
Top guest favourite
Home in Wilmette
4.97 out of 5 average rating, 152 reviews

Unique porcelain-enamel paneled "Lustron" home

MichelleRating, 5 stars2 weeks ago
We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 137 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

LinaRating, 5 stars1 week ago
I loved the little cottage. Quiet neighborhood, felt safe. Restaurants were walkable. Reached out to Marilyn for a breakfast recommendation and checked out bacon and jam, amazing. House was easy to find. Clear instructions. Felt at home.
Guest favourite
Home in Oak Park
4.97 out of 5 average rating, 115 reviews

Garden Unit, King & Queen, Kitchenette & Parking

SarahRating, 5 stars6 days ago
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 :)
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 151 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AndrewRating, 5 stars3 weeks ago
Our hosts were excellent - communicative, welcoming, friendly. We were greeted by Bob who was very laid back and accommodating. He offered good recommendations and amenities during our stay. The space is perfect for large groups and certainly impresses with its charm and personality. The neighborhood is walkable to the Blue Line and many bars/restaurants. Overall 10/10 a perfect stay and would absolutely book again in the future.
Guest favourite
Home in Jefferson Park
4.91 out of 5 average rating, 141 reviews

Chicago getaway for two!

KadilynnRating, 5 stars4 days ago
My boyfriend and I had a fantastic weekend at Gladys’ place. She was super responsive, and check-in was easy with clear instructions. The apartment was cozy and modern, but still felt homey—like our own space for the weekend. It was clean, well-kept, and had thoughtful touches like a Brita pitcher, fresh towels, sheets, and a stocked kitchen. The layout was cute and the decor was simple but perfect—more personality than a hotel room without being cluttered. One of the highlights was the bus stop literally 10 feet from the door, which made getting into southern Chicago (via bus to the Blue Line) super convenient. We also loved walking to Dunkin’ each morning once we realized how close it was. The location felt peaceful but still had a few cute restaurants nearby. We never ran into the hosts, but it felt private even with the shared entry. This stay is in our top 5 Airbnbs—perfect for a couples getaway! Thank you, Gladys, for being such a thoughtful host!

Apartment rentals with a patio

Guest favourite
Apartment in Avondale
4.96 out of 5 average rating, 114 reviews

Lovely top floor 2BR/2BA, steps from everything!

J'HonnaRating, 5 stars1 week ago
The location was great. About 15 min from downtown. The place was beautiful and clean. I would definitely book with Julia again.
Guest favourite
Apartment in Bridgeport
4.9 out of 5 average rating, 116 reviews

Convenient & Spacious 3BR Condo w/Free Parking

AlexisRating, 5 stars2 weeks ago
We enjoyed our stay at Yuyi’s. The space was very clean! There is a beautiful park across the street, delicious restaurants all around, and a grocery store 4 blocks away! We traveled in for business and it was perfect for us, Would love to stay again the next time we are in Chicago.
Guest favourite
Apartment in Pilsen Historic District
4.94 out of 5 average rating, 125 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 starstoday
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!
Superhost
Apartment in Chicago
4.87 out of 5 average rating, 119 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

AlfredoRating, 5 stars2 weeks ago
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.
Guest favourite
Apartment in Lincoln Park
4.91 out of 5 average rating, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars1 week ago
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!
Top guest favourite
Apartment in Lake View
4.98 out of 5 average rating, 118 reviews

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

RebeccaRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Ukrainian Village
4.93 out of 5 average rating, 138 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars5 days ago
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!
Guest favourite
Apartment in West Town
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars3 weeks ago
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.

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

  • Total rentals

    190 properties

  • Nightly prices starting at

    ₹2,564 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

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