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Holiday rentals with a patio in Old Town, Chicago

Find and book unique rentals with patio on Airbnb

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Popular amenities for rentals with patio in Old Town, Chicago

Flat rentals with a patio

Top guest favourite
Flat in West Ridge
5 out of 5 average rating, 28 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

ElizabethRating, 5 starstoday
This is a charming and very comfortable unit. All the amenities are thoughtful and more generous than most other AirBNBs that I’ve stayed. We found the location very convenient to family and Northwestern U, and even getting downtown. The unit was spotless, clean and organized. And exceeded our expectations. Being able to park in the garage was a huge benefit for us. We had a busy schedule with leaving in the morning and not getting back until later evening. It was so nice not to have to search for street parking and not have that worry. We very much enjoyed our stay. This will be our “place” when we return. Elizabeth
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 stars2 weeks ago
Song’s place was perfect for our family trip to Chicago!
Guest favourite
Flat in Cicero
4.97 out of 5 average rating, 310 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

PatriciaRating, 5 stars4 days ago
5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!
Top guest favourite
Flat in Andersonville
4.99 out of 5 average rating, 155 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

DianeRating, 5 stars2 weeks ago
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.
Superhost
Flat in Irving Park
4.78 out of 5 average rating, 142 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 Berwyn
4.9 out of 5 average rating, 302 reviews

The Green Bungalow: Charming 1-BR apt. with patio

MoniqueRating, 5 stars1 week ago
Only got to stay one night but it was a great hidden gem right outside the city! Needed a break from all the hustle and bustle. Had everything I needed, and the bed was so cozy! Christine and Dan always responded to me very quickly. Would stay again!
Guest favourite
Flat in Near West Side
4.98 out of 5 average rating, 108 reviews

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

ChristyRating, 5 stars2 weeks ago
Apartment was great! Rooftop was fantastic and had some nice views. Serg was very communicative and helpful. Parking entrance was slightly out of the way in a back alley but the given instructions included pictures and very detailed instructions. My only complaint is that all of the beds are EXTREMELY firm. My husband and I found it very uncomfortable and I spent one of the nights tossing and turning so much I ended up just laying on the couch. The kids did not seem to mind it.
Guest favourite
Flat in Logan Square
4.86 out of 5 average rating, 112 reviews

Logan’s Cozy Inn.

DustinRating, 5 stars6 days ago
Exactly as described, just what I was looking for. Convenience of proximity to the Blue Line made it very easy for me to check off all the things I wanted to do during my stay. Thanks so much.

House rentals with a patio

Guest favourite
Home in Bridgeport
4.96 out of 5 average rating, 123 reviews

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

KristenRating, 5 stars3 days ago
Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!
Top guest favourite
Home in Wilmette
4.97 out of 5 average rating, 153 reviews

Unique porcelain-enamel paneled "Lustron" home

AnnaRating, 5 stars1 week ago
Such a great place to stay
Guest favourite
Home in Avondale
4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars2 weeks ago
Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!
Guest favourite
Home in East Rogers Park
4.98 out of 5 average rating, 99 reviews

Victorian House in Heart of Rogers Park

LukeRating, 5 stars3 days ago
We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.
Top guest favourite
Home in Lincoln Square
4.98 out of 5 average rating, 115 reviews

Entire first floor in Lincoln Square!

Mary BethRating, 5 stars1 week ago
This is our second stay at this location and we hope to return again in the future. It is a very well-maintained place in a safe location. Also, we love how clean it is!
Guest favourite
Home in Oak Park
4.97 out of 5 average rating, 116 reviews

Garden Unit, King & Queen, Kitchenette & Parking

Anil BabuRating, 5 stars1 week ago
Stayed at Lisa's Airbnb for a.3 day weekend with my family including a 2 year old. We had a great time, great neighborhood, good restaurants- 15 min drive to downtown Chicago and train access as well. The place matched description and my 2 year old played with the hens and chickens in their backyard. Very comfortable beds, clean bathrooms and very responsive host.
Guest favourite
Home in West Town
4.97 out of 5 average rating, 129 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

JamieRating, 5 stars1 week ago
The Airbnb was perfect for my family and I. We have two small kids and this Airbnb was very child friendly! They had tons of kids items we were able to use which saved us packing and toting them through the airport. The hosts were super friendly, very responsive, and went out of their way to make us feel comfortable.
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 stars3 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!

Apartment rentals with a patio

Top guest favourite
Apartment in Lake View
4.99 out of 5 average rating, 157 reviews

Interior Designer’s 2bd 2bath w Private Backyard

ScottRating, 5 stars3 days ago
Matthew's home was incredible! It was a beautiful and comfy space and immaculately clean. The instructions he provided to check-in, where to find things, etc. were very accurate and well thought out. There were more amenities than mentioned in the listing. It really felt like staying in a real home and not a normal Airbnb rental. Matthew was very responsive and really made our stay special. He really went above and beyond any host I have seen before. We were in Chicago for my daughter's college graduation and he made a personalized welcome and congratulations sign in the kitchen just for us. Additionally, on our first morning, there was a chance of rain in the area and on his own, Matthew went out and purchased and provided umbrellas in case we needed them. Above and beyond hosting! I can't recommend this home highly enough!
Guest favourite
Apartment in Avondale
4.96 out of 5 average rating, 116 reviews

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

EdwardRating, 5 stars1 week ago
When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown Chicago.
Guest favourite
Apartment in West Town
4.92 out of 5 average rating, 121 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

MalloryRating, 5 stars1 day ago
Feven was very responsive to all our questions in real time. The place was perfect for four adults and two kids! The place was walkable to a few restaurants and coffee shops and easily drivable to other neighborhoods. We did happen to be in the neighborhood for the PR festival, which we didn’t realize. It made traffic a little tricky but otherwise we didn’t hear too much noise from the festivities. We found a nearby coffee shop and playground which we frequented daily and met lots of friendly neighbors on our walks.
Guest favourite
Apartment in Lincoln Park
4.91 out of 5 average rating, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars1 week 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
Apartment in Lake View
4.98 out of 5 average rating, 119 reviews

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

RebeccaRating, 5 stars2 weeks 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, 139 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!
Guest favourite
Apartment in Lincoln Park
4.96 out of 5 average rating, 106 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

SamiRating, 5 stars1 week ago
This was an excellent place to host a lot of visitors to Chicago! Lots to do nearby, and excellent proximity to the Red Line North/Clybourn station. The home was large, clean, and had such a nice set of helpful earplugs and towels for each bed.
Guest favourite
Apartment in West Loop
4.96 out of 5 average rating, 231 reviews

Updated Designer Duplex In Fulton Market W/parking

NicoleRating, 5 stars3 weeks ago
Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai

Quick stats about holiday rentals with a patio in Old Town, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹6,058 before taxes and fees

  • Total number of reviews

    4.5K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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