
Vacation rentals with a patio in Downtown Chicago
Find and book unique accommodations with an outdoor patio on Airbnb
Top-rated accommodations with an outdoor patio in Downtown Chicago
Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Downtown Chicago accommodations with an outdoor patio
Apartment rentals with a patio

Lovely 2-bedroom apartment in Pilsen
great experience to have, wonderful home !

Spacious! 3 bedroom apartment in Edgewater!
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.

Lovely 2bedroom 1bath Apt and outdoor seating.
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.

2 Room Apartment in Vintage Bldg
We really enjoyed staying at Karen's place. It's a cozy spot in an older building and in a great location in Lakeview where hotels are hard to find. The apartment is not too far from the bus and train to get downtown. Karen was extremely responsive and helpful during our stay.

2BR Apartment Near Chicago
Exactly like the pictures! Was a good place for the short stay!

1 Bedroom Apartment/free parking
We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!

Tree-Lined Street Near the Lake!
This place has the best location. It was easy for me to take the Brown line and get around town. Cute coffee shop bakery on the corner. Mark and Carmen where friendly when we meet in the garden. Nice stay!

Garden Apartment- RickStan Manor
We absolutely loved our stay! The space is beautiful, there’s plenty of room, the neighborhood is amazing, and the beds are incredibly comfortable! The parking space is so helpful as well. It’s one of the best places I’ve stayed at in Chicago - we hope to be back soon!
House rentals with an outdoor patio

European Custom Built Home
The home looks small from the outside but small is the last word I’d use to describe this place. All of the character and space makes this a true hidden gem. Not to mention the full-size basement with plenty room for larger families to enjoy makes this place a perfect booking.

Family Friendly Duplex/9 min from MDW/Free Parking
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.

Your Peaceful,Joyful,Cozy, Relaxing, Experience
This is definitely a gem in the middle of the South Suburbs. The place was really decorated nice, made us feel comfortable and right at home. Erica is a really great host and she is very attentive to any concerns we may have had during our stay. The neighborhood was really quiet and there was a park right on the corner for me to walk my puppy every morning. You will be pleased with this one. I recommend this place to anyone that wants to get away from the hustle and bustle of the big city and wants to enjoy quiet Suburban surroundings. I would definitely stay again, in fact I plan to.

Wrigley classic+trendy+2garage
The house was great. It was located in a neighborhood you could easily walk around. Having garage parking was great, street parking was easy too. The kitchen was fully stocked with every appliance you could want.

Gorgeous and Luxurious 3 BR Home
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.

Quiet cul-de-sac with huge fenced in backyard
Great host and awesome outdoor space with plenty to do nearby.

2BD/1 BA with summer patio in quiet Roscoe Village
We had a wonderful stay! Everything was so lovely. It is a spacious place and adorable neighborhood. Had no problem navigating public transport to downtown. Thanks so much!!

3BR Jazz Club Themed House ~Kids Game Room, Patio
Our family enjoyex our stay!
Condo rentals with a patio

Loft-Like Wicker Park Condo Steps from the Cta!
Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.

Convenient & Spacious 3BR Condo w/Free Parking
Great place in a quite neighborhood. Close to the convention center and really close to some awesome restaurants.

Luxuriously bright 3-bedroom condo: The Treehouse
very clean and wasn't musty 5/5 stars

The Ramblers Inn, Northside NEW Reno w/parking!
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.

Urban Oasis | Great for Families w/ Kids
We had a fantastic stay! Everything inside the home is easy to find and we'll labeled. The location is great on a quiet street. We always had a parking space available. The master bathroom is very luxurious with the shower being the star of the show! We will definitely be booking again when in Chicago!

Logan Square Beauty with 2 Bedrooms W/parking
Smooth communication, nice location

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
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.

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
Had a great stay in this Airbnb! The location was fantastic—super convenient for public transit. The place was spotless and very comfortable, making it a great spot to work from home. If the weather had been warmer, I definitely would have taken advantage of the awesome outdoor area. Highly recommend!
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Frank Lloyd Wright Home and Studio
- Shedd Aquarium
- The Field Museum
- 875 North Michigan Avenue
- Illinois Beach State Park
- Woodlands Course at Whittaker
- Guaranteed Rate Field
- Skydeck Chicago
- Odyssey Fun World
- Bengtson's Pumpkin Farm and Fall Fest
- Splash Station
- Olympia Fields Country Club
- Flossmoor Golf Club
- Deep River Waterpark
- Villa Olivia
- The Water Works Indoor Water Park
- Chicago Golf Club
- The 606
- Raging Waves Waterpark
- Four Lakes Alpine Snowsports
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