Holiday rentals with a patio in Chicago Loop

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

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Popular amenities for Chicago Loop Holiday Houses with Outdoor Verandahs

Apartment rentals with a patio

Superhost
Apartment in Chicago
4.86 out of 5 average rating, 113 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.
Top Guest favourite
Apartment in Forest Park
4.99 out of 5 average rating, 156 reviews

Sunny 1 bedroom apartment 1 block from restaurants

EleanorRating, 5 stars1 week ago
Jim was a fantastic host. Very responsive and timely in his communications and support for our needs during our stay in their place. Their home was comfortable and well appointed with additional amenities you don't often see in AirBnB spaces, like N'espresso appliances and supplies. We would definitely consider repeat visits! Thank you, Jim!
Superhost
Apartment 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
Apartment 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
Apartment in Forest Park
4.87 out of 5 average rating, 255 reviews

Home in Forest Park Upstairs.

AmberRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Irving Park
4.9 out of 5 average rating, 52 reviews

Montrose Gardens

AndrewRating, 5 stars2 weeks ago
Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed
Guest favourite
Apartment in Logan Square
4.86 out of 5 average rating, 109 reviews

Logan’s Cozy Inn.

SandraRating, 5 stars3 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
Apartment in Avondale
4.96 out of 5 average rating, 26 reviews

Lovely Garden Studio Apartment.

JessicaRating, 5 stars5 months ago
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.

Holiday House Rentals with a Verandah

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.
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 Lincoln Park
4.94 out of 5 average rating, 104 reviews

Luxury SOHO Styled Two-Level Townhouse | Old Town

HarrisonRating, 5 stars3 weeks ago
Very responsive. Had a wonderful stay, just as advertised. Great neighborhood
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

ShaniaRating, 5 stars1 week ago
I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!
Superhost
Home in Chicago
5 out of 5 average rating, 4 reviews

Luxury-Near Downtown & United Center-Sleeps 14

AlexisRating, 5 stars4 days ago
Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!
Guest favourite
Home in West Town
4.97 out of 5 average rating, 127 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

Katy Rating, 5 stars2 weeks ago
Lovely place! Nathaniel was very responsive and accommodating to us while in Chicago! Made everything easy and created a homey space for us to enjoy. Would definitely stay again.
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars2 weeks ago
Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!
Top Guest favourite
Home in Oak Park
4.98 out of 5 average rating, 161 reviews

Clean, Cozy 1st Floor Flat, Kitchen, Parking

PariRating, 5 stars2 weeks ago
This was our second time staying here, and everything was as comfortable as the first time. We highly recommend this place.

Holiday condos with a patio

Guest favourite
Condo 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
Condo in West Town
4.92 out of 5 average rating, 120 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

RachaelRating, 5 stars1 week ago
Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.
Top Guest favourite
Condo in East Rogers Park
4.98 out of 5 average rating, 108 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

KerryRating, 5 stars1 month ago
Easy check in and close to LUC which is what we needed. Clean and comfortable. Bonus that it included parking.
Guest favourite
Condo in Pilsen Historic District
4.94 out of 5 average rating, 125 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 stars3 days ago
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
Condo 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
Condo in Lincoln Park
4.91 out of 5 average rating, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars3 days ago
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.
Top Guest favourite
Condo 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
Condo in Ukrainian Village
4.93 out of 5 average rating, 138 reviews

Modern Chicago Movie Themed Apt

LechelleRating, 5 stars1 week 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!

Quick stats about holiday rentals with a patio in Chicago Loop

  • Total rentals

    270 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    9.8K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    160 properties allow pets

  • Rentals with a pool

    200 properties have a pool

Destinations to explore

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