
Vacation rentals with outdoor seating in Woodlawn, Chicago
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Top-rated outdoor seating rentals in Woodlawn, Chicago
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Popular amenities for Woodlawn, Chicago outdoor seating rentals
House rentals with outdoor seating

The Modern Muse of Chicago! Close to everything!
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!

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

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Unique porcelain-enamel paneled "Lustron" home
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!

Retro Modern Bungalow | fire pit | free parking
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.

Quiet cul-de-sac with huge fenced in backyard
Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.

The Spa of Downtown Whiting
My partner and I absolutely loved our stay at Steven’s place. It was exactly what we were looking for. The spa tub was amazing. Walking distance to the beach and the local shops! Steven gave several recommendations for places to check out. We went to dinner at a local bar and walked 119th street to check out the small businesses! It is the perfect in between spot to stay for Chicago and The Dunes! The place was just like the pictures, with comfortable beds, nice couches and surround sound! Definitely one of our best stays! We hope to visit again before the end of summer!
Apartment rentals with outdoor seating

Plant MOOD FREE Wi-fi, parking, washer & dryer!
We really enjoyed our stay. The place was very clean and welcoming. The bathroom had a nice shower with good water pressure. The bed was comfortable and provided a restful sleep. Any questions I had, Siobhan responded very quickly and pleasantly. We went to a beer festival in nearby Munster and this was a great location to stay in.

Walk to Oak Park from this Newly Remodeled Gem
Uncommonly well supplied and furnished, this is one of our favorite Airbnbs anywhere. We’ve stayed a few times, and our experience has always been exceptional.

*A Happy (City) Glamping- walk to train FREE park
The space is exactly as described. Loved how close it was to public transportation. The space is great for a weekend away.

Designer Avondale Attic
Just wonderful. That was one of the nicest places I've ever been. The apartment is totally lovingly furnished. Everything was super clean and tidy. There are even toothbrushes, toothpaste and a sleeping mask if you need them. The kitchen is also super equipped with everything you need. The short walk to the metro was also very convenient. We would definitely come back.

Charming Unique 2 Bdrm Apartment in Victorian Home
Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!

South Loop 3Br/2Ba Condo with Balcony & Parking
Got lucky finding this place. Excellent experience. Great owner. Everything was neat, clean, and super easy. We will gladly be back. Great job!

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

Private apartment with retro vibe
Place was centrally located with lots to do in walking distance for food and entertainment. We could walk to the venue where we saw our live music. The host is very kind and had a lot of information about the area to share with us. We felt very safe the house was peaceful very clean. The outdoor garden area is really pretty too. We definitely wanna stay here the next time we’re up for a show.
Condo rentals with outdoor seating

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

3 BR Summer GetAway, 15mins to Loop+Gated Parking
Close to the green line for easy transportation.

The Urban Oasis | Outdoor Lounge • Sleeps 10+
The unit was as described, clean, affordable, easy to get to and home base from, and the neighborhood felt safe. There’s a coffee shop right on the corner we walked to in the mornings. We had a big group for a bachelorette and there was plenty of spaces to sleep downstairs (3 bedrooms with beds and one shared space with four beds), get ready (2 full bathrooms including two baths for kiddos), and lounge all together (large couch, big kitchen table, island seating, and outdoor covered area). Big thing for me is ceiling fans the bedrooms so that was super satisfying. Highly recommend this unit and we’d go back!

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Great place! Everything was clean, in a good location and they communicated well.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
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.

Modern Chicago Movie Themed Apt
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!

Spacious 4 Bedroom Condo
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.

Wicker Park/Bucktown condo with large balcony
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 vacation rentals with outdoor seating in Woodlawn, Chicago
Total rentals
40 properties
Nightly prices starting at
G$6,276 GYD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park