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

Superhost

Flat

4.87 out of 5 average rating, 101 reviews

Lovely 2-bedroom apartment in Pilsen

LayssRating, 5 stars1 month ago
We wanted a place by our friends house. This was perfect, cute place, had all the basics and host was cute to have some water and snacks for us.
Guest favourite

Flat

4.94 out of 5 average rating, 68 reviews

Spacious! 3 bedroom apartment in Edgewater!

E MRating, 5 stars1 month ago
Great place. Spacious, clean, quiet. If this is the neighborhood you're looking for then this is a aces.
Guest favourite

Flat

4.98 out of 5 average rating, 103 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

AlyssaRating, 5 stars1 month ago
Great home in a great area! We loved the house it was just what we needed for our trip to Chicago.
Guest favourite

Flat

4.97 out of 5 average rating, 33 reviews

2 Room Apartment in Vintage Bldg

RitaRating, 5 stars1 week ago
Karen was incredibly responsive. She brought over a futon for a friend who stayed with me for some nights and when the hair dryer broke down, she got a replacement within a half hour. The kitchen was well stocked...really appreciated the half & half for my coffee. Fantastic towels. It is also 2 blocks to a zip-car location which is a great way to have the flexibility of a car without the hassle of trying to find parking. Definitely would stay again.
Guest favourite

Flat

4.88 out of 5 average rating, 110 reviews

2BR Apartment Near Chicago

MegRating, 5 stars1 week ago
Thank you it was perfect for our needs and looked as the pictures showed! Would definitely stay again !
Guest favourite

Flat

4.96 out of 5 average rating, 79 reviews

Beautiful private apartment completely Renovated.

CeleneRating, 5 stars2 months ago
Very clean; great location; ample parking
Superhost

Flat

4.85 out of 5 average rating, 27 reviews

1 Bedroom Apartment/free parking

JennaRating, 5 stars6 months ago
Karolina gave through instructions for check in. I ran into no issues during my stay. The apartment was clean, spacious, and comfortable!
Guest favourite

Flat

4.86 out of 5 average rating, 240 reviews

Home in Forest Park downstairs.

AndreRating, 5 starstoday
It’s a great place to stay whenever you’re just trying to get away for a little while. Super cozy and beautiful kitchen. Felt right at home !

House rentals with a patio

Superhost

Home

4.92 out of 5 average rating, 26 reviews

European Custom Built Home

BobbyRating, 5 stars4 weeks ago
What a cool house! This was the perfect solution for being away from Indiana for a night with family. The house is HUGE inside, and real charming. Would love to stay again sometime.
Guest favourite

Home

4.94 out of 5 average rating, 34 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

NoelleRating, 5 stars1 week ago
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!
Guest favourite

Home

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

KatieRating, 5 stars4 months ago
Lilly was prompt in her responses and very helpful. The place was well kept and clean. A quick Uber ride to downtown. Our group really enjoyed our stay!!
Guest favourite

Home

4.96 out of 5 average rating, 113 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Fire Pit

ChrisRating, 5 stars2 months ago
Wonderful stay at this Air B&B, loved the space! A perfect retreat for an adult getaway! The layout was nice for two couples with two en-suite bedrooms and off street parking. The hot tub was clean and chemically balanced. Checking in and out was very easy with no chores (a unique and appreciated feature). Adequately stocked for kitchen. Bed was comfortable and the place was clean! The host was one of the most responsive and attentive hosts we have experienced. The host also checked in to ensure the stay was going well. Provided a good balance of engagement without being overbearing. The space and host are highly recommended. Would stay again and would consider other locals with the same host if available.
Guest favourite

Home

5 out of 5 average rating, 10 reviews

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

YoussefRating, 5 stars4 weeks ago
Great place, beautifully decorated with all the amenities needed and a very accommodating host. It is in close proximity to a bunch of restaurants, cafés and event spaces. We will not hesitate to stay here again.
Guest favourite

Home

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars3 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.
Guest favourite

Home

4.93 out of 5 average rating, 27 reviews

Hidden Gem on the CHI north side

ChristophRating, 5 stars3 months ago
Christian’s place reminds me of the good old times when Airbnbs weren’t run by corporations. This place has charm. It’s cozy. The owner takes pride in it. I will come back!
Guest favourite

Home

4.93 out of 5 average rating, 114 reviews

Quiet cul-de-sac with huge fenced in backyard

JamiaRating, 5 stars1 week ago
Our stay was great! Great location! Tom was very accommodating. Would definitely stay again when I’m in town

Apartment rentals with a patio

Superhost

Apartment

4.84 out of 5 average rating, 182 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

LauraRating, 5 stars1 month ago
Our 2nd time stay with Tom was as easy and enjoyable as the first. Location is great, walkable and easy. We'll come back again in the future as travel necessitates.
Guest favourite

Apartment

4.9 out of 5 average rating, 107 reviews

Convenient & Spacious 3BR Condo w/Free Parking

DonnaRating, 5 stars1 month ago
I have stayed at Yuyi’s place multiple times. It’s big, airy and very comfortable. I had special circumstances this last trip and Yuyi was very accommodating. I highly recommend this place .
Guest favourite

Apartment

4.92 out of 5 average rating, 109 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

PeterRating, 5 stars4 weeks ago
Feven's third-floor condo met the billing exactly. We had a ton of space to socialize, everyone got a bed (there are four beds and we could have had 7 people there) - not many AirBnB's can support that many people. Our four people were super comfortable. The kitchen was well stocked and had a big tub of ground coffee for us in the morning. Feven was great at communicating. We'd stay here again.
Guest favourite

Apartment

4.89 out of 5 average rating, 108 reviews

Unique 2BR/2BA FREE Parking/WI-FI Minutes From DT

TaniyaRating, 5 stars3 weeks ago
Will be staying again, Cory is one of the best host I’ve came across.
Guest favourite

Apartment

4.98 out of 5 average rating, 103 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

JessicaRating, 5 stars1 week ago
We had a wonderful, peaceful time staying with Jeremiah and Maysa. They were kind, extremely communicative, and when our family came over to visit everyone commented on what a beautiful home it was. 10/10. Also, extremely fast WiFi, great for working from home for multiple people who were on video calls.
Guest favourite

Apartment

4.94 out of 5 average rating, 108 reviews

Urban Oasis | Great for Families w/ Kids

RobynRating, 5 stars3 weeks ago
Our crew of 11 fit well here. Alex was a great host that tossed in some extras for us at no charge! The house was on a quiet street and was beautiful. There were games for adults and kids available. The extras provided for kids were wonderful to not have to pack along for the quick trip. He had a baby gate, pack n play, highchair and more. There were some basics missing from the kitchen that made it a little interesting to cook but overall, it was a good stay.
Guest favourite

Apartment

4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KendraRating, 5 stars1 month ago
John’s place was clean and cozy. The kitchen was immaculate and we appreciated the nespresso machine and pods. The location was excellent, many food and drink choices right outside the door. It was amazing to have our own parking spot! There are a lot of stairs but that is expected in the city. I would definitely recommend this spot to my friends.
Guest favourite

Apartment

4.98 out of 5 average rating, 111 reviews

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

SamiRating, 5 stars3 days ago
This Airbnb is a hidden gem situated in the vibrant heart of Boystown. You will be residing in a spacious and modern home, graciously owned by the most attentive and hospitable hosts. If you are fortunate enough to secure a stay here, you will embark on an unforgettable experience.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    £55 before taxes and fees

  • Total number of reviews

    4.2K 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