Holiday rentals with a patio in Old Town, Chicago

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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, 29 reviews

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

ElizabethRating, 5 stars3 days ago
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
Top guest favourite
Flat in Uptown
4.96 out of 5 average rating, 46 reviews

2 Room Apartment in Vintage Bldg

JonathanRating, 5 stars2 days ago
This apartment was a great value in a convenient location, just what I was looking for. Fresh flowers and wine waiting for me didn’t hurt a bit either. Quaint balcony off the bedroom provided cool breezes on a hot (almost) summer day! Thanks for your hospitality Karen, I’ll be back!
Guest favourite
Flat in West Lake View
4.95 out of 5 average rating, 189 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

MarcelRating, 5 stars1 week ago
Great space. Actually even bigger in person than what the images are showing. Superb location. Very close to restaurants and public transport as so easy. Also walking distance to the Chicago Music Exchange, if you’re a guitar player it’s the place to visit. Sam was also extremely responsive.
Top guest favourite
Flat in West Town
4.99 out of 5 average rating, 85 reviews

Humboldt Park Retreat: Skylights & Queen Beds

MollyRating, 5 stars2 days ago
We were so impressed with this airbnb! It was immaculately clean and beautifully decorated. It was very peaceful and quiet to come back to after our busy days exploring the city. We especially loved the kitchen amenities like high quality olive oil and two types of filtered water! Christine thought of everything! We’d love to come back again!
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 Irving Park
4.91 out of 5 average rating, 54 reviews

Montrose Gardens

JoyceRating, 5 stars1 week ago
This was a very cute one bedroom apartment. It was perfect for my husband, myself and my daughter. Extremely clean. So sweet they left treats and snacks! Host was very nice and accommodating. Would definitely stay again!
Guest favourite
Flat in Logan Square
4.86 out of 5 average rating, 112 reviews

Logan’s Cozy Inn.

DustinRating, 5 stars1 week 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.
Superhost
Flat in Logan Square
4.86 out of 5 average rating, 122 reviews

Private Garage+Laundry+Restaurant Row+93 Walkscore

EmilyRating, 5 stars6 days ago
Another great stay! Eva is a great host and ensured that everything was well stocked and ready for my stay. The location was great for outdoor running, just a block from an entrance to the popular 606 Trail. 5 stars!

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 stars6 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, 154 reviews

Unique porcelain-enamel paneled "Lustron" home

JulietRating, 5 stars1 day ago
I enjoyed my stay here which enabled me to be close enough to Northwestern’s campus as I worked on a writing project. Being minutes from downtown Wilmette was a plus—be sure to check out Saint Roger’s Abbey bakery for wonderful French pastries! The house was neat, tidy, and matched the description. I also appreciated the record collection!
Guest favourite
Home in Avondale
4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars3 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!
Top guest favourite
Home in Logan Square
5 out of 5 average rating, 26 reviews

Sunny Historic Cottage on the Park

MichelleRating, 5 stars6 months ago
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.
Top guest favourite
Home in Lincoln Square
4.98 out of 5 average rating, 116 reviews

Entire first floor in Lincoln Square!

CaitlinRating, 5 starstoday
We spent a fantastic week in Nora’s home and it felt very much like our home for the week. The apartment was much more spacious than we expected and everything was exactly as described. We found parking easily each day and enjoyed how walkable the home was to local amenities. The drive to downtown was about 35 min, making it a convenient spot, and the chance to enjoy a real Chicago neighborhood experience. Highly recommend for other travelers, including those with families!
Top guest favourite
Home in West Town
4.97 out of 5 average rating, 38 reviews

jane's house - a boutique flat in west town -2b/1b

NathanRating, 5 stars1 day ago
We absolutely loved staying at Amy’s place! Easy check in/check out, great communication by the host, and plenty of room for 2 adults and 2 kids to stretch out. The mid century vibe was a nice bonus. Would 10/10 stay here again.
Top guest favourite
Home in Lincoln Park
4.94 out of 5 average rating, 72 reviews

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

AdriaRating, 5 stars2 weeks ago
Wow! I can’t say enough good things about Cheryl’s hosting! She and her husband went above and beyond for us. They are so responsive and friendly and even went so far as buying a pack and play for us last minute and jumping our car battery when it died! Talk about amazing! The place had everything we needed and the location was lovely. Would definitely stay here again!
Guest favourite
Home in Chicago
4.86 out of 5 average rating, 140 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

BritaniRating, 5 stars2 weeks ago
It was a nice break from the hustle and bustle of the big city. A few great restaurants just a couple blocks away. And just a block away from bus stops.

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 stars6 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!
Superhost
Apartment in Wicker Park
4.84 out of 5 average rating, 186 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

LaurenRating, 5 stars1 month ago
Tom’s place was exactly what we needed for a weekend in Wicker Park! The location was perfect to enjoy restaurants and stores, and the ease of access with the keypad was great for check-in and coming/going. The unit was very clean and spacious, and having a dedicated parking spot was amazing! Would definitely stay here again.
Guest favourite
Apartment in West Town
4.92 out of 5 average rating, 121 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

MalloryRating, 5 stars4 days 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.
Superhost
Apartment in Logan Square
4.78 out of 5 average rating, 258 reviews

Logan Square Beauty with 2 Bedrooms W/parking

JamesRating, 5 stars2 weeks ago
Matt is a great host. Open, responsive and informative…everything you want really when on vacation
Top guest favourite
Apartment in West Town
4.97 out of 5 average rating, 146 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

MichaelRating, 5 stars6 days ago
Great place! Everything was clean, in a good location and they communicated well.
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 stars2 weeks 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 stars1 month 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 Old Town, Chicago

  • Total rentals

    40 properties

  • Nightly prices starting at

    $90 SGD 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

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