
Vacation rentals with outdoor seating in Chicago
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Top-rated outdoor seating rentals in Chicago
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House rentals with outdoor seating

Duplex Home RoscoeVillage/Wrigley Free St Parking
What a lovely home! We and our two daughters had a great stay. The master bedroom is quite spacious, the beds are comfortable, there was ample closet space, and the kitchen is fantastic! The Roscoe Village neighborhood more generally is charming and walkable to any trips for essentials (multiple grocery stores and pharmacies within half a mile). While the Cubs were on the road during our trip, the house is an easy 20-minute walk to Wrigley Field. And Sharleen was always prompt and very helpful in answering the questions we had. We would happily return!

Maywood Relaxation
We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

Cozy House, Main Road Access, Close to Colleges
Vic's place was a convenient place to relax in between graduation weekend events. Close to jumping onto any of the major roads to the city or other suburbs but also the town of Lisle has great restaurants right there. The home is right on a busy road but surprisingly quiet once you're inside. We had a few gorgeous spring days and were able to sit outside on the patio enjoying time with extended family which was a definite perk. Thanks, Vic!

Casa PLZN Location | Entire Home | Garage Parking
We had a wonderful stay. The place was clean, comfortable, and had enough space for our larger group. It was really nice getting to use the garage parking space and the outdoor area is cozy. After day 1, we did have trouble getting into the place through the front door keypad, there was a battery issue. Thankfully there is access to the home through the back door/garage. Thanks for a great stay!

BoHo House - A Chic, 1903 Chicago Workers Cottage
My family and I had a fantastic stay! The space was exactly as described; clean, stylish, and thoughtfully designed. Check-in was smooth, and Adam was super helpful throughout our visit. We especially appreciated the backyard for our dogs . The location was perfect. It was close to everything we needed but still quiet and peaceful. Would absolutely stay here again and highly recommend to anyone visiting the area!

Spacious Home in Chicago Suburbs
This was a great spot for our larger group to stay during our visit to Chicago! Many places to eat nearby and spacious enough for everyone. The spit floor plan was also great as it gave our group different common areas to hang out in as well! The host was very accommodating for a late check out as well! Would certainly stay again!

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Quiet cul-de-sac with huge fenced in backyard
A great spot!! A friend and I were in town for a concert and this place was perfect! The patio was really cool and Tom has the cutest dog!!
Apartment rentals with outdoor seating

The Banksy-Greystone Rooftop Firepit United Center
I really enjoyed my stay at the Banksy.

iKlektik House Chicago / Robin
Mindy & Tony’s place was a nice hidden gem. Their home was cozy and includes all you need for a stay in Chicago. There was plenty of street parking and the area is quiet. I would highly recommend for a solo traveler or couple.

Modern 3BR with Private Rooftop & Free Parking
It was very clean and comfortable beds/beddings. Great for a few night stay with family.

Lovely 2bedroom 1bath Apt and outdoor seating.
10/10 - already booked again for a second trip

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis
Super great living area and the outside patios were awesome. Really liked the inside sitting areas looking out over patio as well. Easy to find a quiet spot from family🤭

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!

Charming retreat w/ fireplace
Me And my fiancée had a great time, clean place, and worth every cent, only downside is parking.

Executive Apartment on Lake Michigan with parking
No problem except for us French to find out how the cooking utensils work and in particular the hood, a manual would be good, too bad for the bad weather the exteriors would have deserved to be used but the weather is not part of the package
Condo rentals with outdoor seating

Convenient & Spacious 3BR Condo w/Free Parking
Loved this condo. We had 7 adults staying and felt comfortable. Having a dedicated parking space was super helpful and on street parking was easy. Please note this is a 3rd floor walk up so if stairs are a problem you need to consider if this works for you. Easy access to Midway airport and Chinatown were also great features.

Urban Oasis | Great for Families w/ Kids
Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
This was a fabulous place to stay! My brother and I could easily walk to the "L" and head downtown. The pizza place right downstairs was delicious - we ate there twice in three days! The beds were comfortable, the couch and living room set up was cozy. I would absolutely stay there again!

Authentic Condo steps from Wrigley Field!
Absolutely loved this apartment! You can not have a better location in Wrigleyville. My only “bad” feedback was the neighbors. Can you really smoke weed all day long?

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

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.

Luxurious River North 3BR/2BA- Free Onsite Parking
Great responsive host. The place was clean and check in was easy. They were very responsive and accommodating. The location was excellent and easy to navigate with plenty to do within walking distance.

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 Chicago
Total rentals
2.7K properties
Total number of reviews
188K reviews
Family-friendly rentals
1.8K properties are a good fit for families
Pet-friendly rentals
920 properties allow pets
Rentals with a pool
290 properties have a pool
Rentals with dedicated workspaces
2.2K properties have a dedicated workspace
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