Holiday rentals with a patio in Woodlawn, Chicago

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Popular amenities for rentals with patio in Woodlawn, Chicago

Flat rentals with a patio

Guest favourite
Flat in Pilsen
4.92 out of 5 average rating, 103 reviews

Mins. to Downtown & West loop! Entire Apt.

AmyRating, 5 stars2 weeks ago
This listing is exactly like the pictures, no frills but comfortable and at a great price. We had family living close by so the location was perfect, will stay again. Thank you!
Top guest favourite
Flat 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!
Guest favourite
Flat in Maywood
4.92 out of 5 average rating, 101 reviews

Cozy guest studio, great for couples!

BrittanyRating, 5 stars1 week ago
Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!
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.
Guest favourite
Flat in Forest Park
4.82 out of 5 average rating, 284 reviews

Home in Forest Park downstairs.

ChrisRating, 5 stars1 day ago
Sabin's home is amazing and always a perfect stay for me when I'm passing through. Clean, updated everything and HUGE TV, comfy beds and pillows. And he's a great host and responds quickly if anything comes up. This is my 2nd stay and I'll be returning again next time I'm passing through
Superhost
Flat in South Loop
4.77 out of 5 average rating, 102 reviews

McCormick 2B/2Ba for up to 6 guests/private Patio

LouRating, 5 stars1 month ago
Good place to stay, I would definitely stay here again. This place has a security guard downstairs so it feels safe. The unit was clean and easy to get around the city.
Guest favourite
Flat in Berwyn
4.9 out of 5 average rating, 303 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 West Town
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.

House rentals with a patio

Guest favourite
Home in South Side
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars5 days ago
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!
Guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 246 reviews

Division St Designer Home In Heart of Wicker Park

MatthewRating, 5 stars2 weeks ago
I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!
Superhost
Home in Chicago
4.9 out of 5 average rating, 10 reviews

Cozy Modern Home w/Fireplace & Pond

JazsminRating, 5 stars4 months ago
The host was very nice and attentive. The place was very nice and clean. Great place to stay
Guest favourite
Home in Humboldt Park
4.95 out of 5 average rating, 63 reviews

Private Logan Square Garden Apt

TiffanyRating, 5 stars6 days ago
Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!
Top guest favourite
Home in Chicago
4.98 out of 5 average rating, 100 reviews

Victorian House in Heart of Rogers Park

LukeRating, 5 stars4 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.
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 Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.
Top guest favourite
Home in North Kenwood
5 out of 5 average rating, 23 reviews

Villa Noir Chicago Victorian 7 min to downtown

EddieRating, 5 stars2 weeks ago
Great place. Great communication. Perfect for what we needed. Great house. Great neighborhood, right outside of downtown.

Apartment rentals with a patio

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 Pilsen
4.9 out of 5 average rating, 117 reviews

Convenient & Spacious 3BR Condo w/Free Parking

CatherineRating, 5 stars1 week ago
Good location. Condo was very clean with comfy beds. There are 3 flights of stairs to get to condo- no problem for us but be aware
Guest favourite
Apartment in Pilsen
4.94 out of 5 average rating, 126 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

MelissaRating, 5 stars1 week 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
Apartment in Chicago
4.87 out of 5 average rating, 120 reviews

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

MelissaRating, 5 stars2 days ago
Awesome location, near lots of local restaurants, public transit and a major grocery store. China Town is a short bus ride away. The neighborhood itself is awesome, helpful neighbors and very friendly local vendors. The apartment itself is clean, inviting and has everything you could possibly need. Cory and Alexis were very inviting host, quick to respond to my questions and were very informative. I will be keeping this location in mind for my future Chicago travels.
Top guest favourite
Apartment in West Town
4.97 out of 5 average rating, 145 reviews

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

AnthonyRating, 5 stars1 week ago
This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.
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 Bucktown
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

ErinRating, 5 stars1 month ago
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!

Quick stats about holiday rentals with a patio in Woodlawn, Chicago

  • Total rentals

    110 properties

  • Nightly prices starting at

    ₹2,603 before taxes and fees

  • Total number of reviews

    3.7K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

Destinations to explore

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