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Vacation rentals with outdoor seating in Wicker Park, Chicago

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Wicker Park, Chicago outdoor seating rentals

House rentals with outdoor seating

Guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport
4.96 out of 5 average rating, 122 reviews

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

LuciaRating, 5 stars1 week ago
We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.
Guest favorite
A spacious living area features a large sectional couch, adorned with decorative pillows. A sleek coffee table sits in front, and a framed cityscape photograph hangs on the wall. Natural light illuminates the space through three windows, enhancing the welcoming atmosphere.
Home in Roscoe Village
4.92 out of 5 average rating, 288 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

AlexanderRating, 5 stars1 week ago
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!
Superhost
A modern kitchen is characterized by dark wood cabinetry and stainless steel appliances. A spacious dining table is surrounded by four chairs. Natural light enters through a door, which leads to the outside, creating a bright and functional cooking space.
Home in Maywood
4.76 out of 5 average rating, 123 reviews

Maywood Relaxation

MadiRating, 5 stars3 days ago
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.
Superhost
An open-concept living area features high wooden beams and a large flat-screen TV mounted on a dark accent wall. A stylish dining table accommodates six, while the kitchen showcases modern cabinetry and stainless steel appliances. Natural light fills the space through nearby windows.
Home in Chicago
4.87 out of 5 average rating, 106 reviews

Casa PLZN Location | Entire Home | Garage Parking

RachelRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Avondale
4.94 out of 5 average rating, 147 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

MaitlandRating, 5 stars1 week ago
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!
Guest favorite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.92 out of 5 average rating, 137 reviews

Quiet cul-de-sac with huge fenced in backyard

AshleyRating, 5 stars5 days ago
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!!
Guest favorite
The exterior view of the custom Prairie-inspired home is presented, featuring a stone facade and wooden accents. Turquoise doors serve as the entrance, flanked by light fixtures. Lush greenery surrounds the pathway leading to the front, while blooming trees and shrubs enhance the serene setting.
Home in Justice
4.93 out of 5 average rating, 225 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

KimberlyRating, 5 stars1 month ago
Thank you thank you! We were comfortable and loved the ease of your booking! It's a beautiful home and I definitely left it as so. Again it's worth the stay!
Superhost
A landscaped outdoor space features a stone path leading through patches of green grass. Various planters display blooming flowers, while a cozy seating area is situated on one side. Wooden stairs ascend to the upper level of the building, surrounded by trees and shrubs.
Home in Chicago
4.93 out of 5 average rating, 105 reviews

Beautiful Chicago Greystone

DavidRating, 5 stars1 week ago
Thanks to Micheal me and my friends had a blast in the surrounding areas of the place very fast to respond and very helpful thanks for the amazing place will definitely book again if i go back to chicago

Apartment rentals with outdoor seating

Guest favorite
A private rooftop patio is displayed, featuring a seating area with bright orange cushions on a dark wicker couch. A glass table is centrally placed, surrounded by panoramic views of the Chicago skyline under a partly cloudy sky.
Apartment in Near North Side
4.91 out of 5 average rating, 141 reviews

Modern 3BR with Private Rooftop & Free Parking

JaneRating, 5 stars3 weeks ago
It was very clean and comfortable beds/beddings. Great for a few night stay with family.
Guest favorite
A cozy living area features a modern black sectional sofa adorned with colorful throw pillows. A large photograph of a city skyline hangs on the wall. A small coffee table rests on a patterned rug, while a desk and chair are positioned beside a plant and shelves.
Apartment in Avondale
4.97 out of 5 average rating, 109 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JoseRating, 5 stars2 weeks ago
10/10 - already booked again for a second trip
Guest favorite
An elevated outdoor space features multiple levels, including an upper deck with railing. Lush greenery and carefully arranged seating areas create an inviting atmosphere. The exterior of the structure is painted in soft hues, and large windows allow for ample natural light.
Apartment in Humboldt Park
4.98 out of 5 average rating, 100 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

KeithRating, 5 stars3 weeks ago
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🤭
Guest favorite
A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.
Apartment in Evanston
4.82 out of 5 average rating, 181 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

NicholasRating, 5 stars1 month ago
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!
Superhost
A modern living area features a green sectional sofa, complemented by decorative pillows and a round coffee table. Exposed wooden beams and industrial-style ductwork are visible on the ceiling. A small window allows natural light, highlighting the textured gray walls and wooden flooring.
Apartment in Chicago
4.84 out of 5 average rating, 100 reviews

Charming retreat w/ fireplace

RicardoRating, 5 stars3 weeks ago
Me And my fiancée had a great time, clean place, and worth every cent, only downside is parking.
Superhost
An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.
Apartment in East Rogers Park
4.9 out of 5 average rating, 173 reviews

Executive Apartment on Lake Michigan with parking

FrankRating, 5 stars1 week ago
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
Guest favorite
A bright living area features large windows adorned with patterned curtains, allowing natural light to fill the space. Comfortable seating is arranged around a circular table, complemented by an area rug with bold colors. A cozy accent chair and ottoman add to the inviting atmosphere.
Apartment in Oak Park
4.92 out of 5 average rating, 185 reviews

Large sunny 3BR apt. in downtown Oak Park

AlexanderRating, 5 stars1 month ago
This is a great Airbnb - really clean and very pleasantly and thoughtfully furnished. In a world of Airbnbs out of an IKEA catalogue this stood out. It’s a really nice space to spend time in, with a large and sunny living/dining area. Michelle was also extremely responsive and friendly.
Guest favorite
A modern dining area is presented, featuring a white rectangular table surrounded by six chairs. A decorative centerpiece sits on the table. The open layout connects to a bright living space with a couch and shelving in the background, enhancing the inviting feel of the apartment.
Apartment in Chicago
4.84 out of 5 average rating, 116 reviews

Spaulding Oasis on 4 lots In Humboldt Park!

AnnyaRating, 5 stars2 weeks ago
This was a great stay! The Airbnb so NICE, I felt safe and the neighbors were very kind. I would definitely stay here again as it’s a little bit outside the city but it was peaceful and quiet.

Condo rentals with outdoor seating

Guest favorite
A comfortable living area features a plush sectional sofa and a cozy armchair. A wooden coffee table is positioned centrally, while a television is displayed on a dark media unit. Natural light enters through multiple windows, highlighting the room's stone accent wall.
Condo in Woodlawn
4.87 out of 5 average rating, 236 reviews

A Stones Throw from U Chicago South Campus!

JoanRating, 5 stars3 weeks ago
This was my second stay at Luke’s and just like last time, I had a clean, quiet, comfortable place to stay. Checking in was easy and flexible, and Luke graciously offered early check in. He also invited us to join him to learn about bees in the backyard that afternoon, which one of us was able to take him up on! Luke was responsive and proactive about communicating, and provided clear instructions on everything to do with our stay. I hope to stay there again in the future!
Guest favorite
A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.
Condo in Pilsen
4.9 out of 5 average rating, 115 reviews

Convenient & Spacious 3BR Condo w/Free Parking

MichelleRating, 5 stars2 weeks ago
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.
Guest favorite
A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.
Condo in Pilsen
4.93 out of 5 average rating, 123 reviews

Urban Oasis | Great for Families w/ Kids

RichardRating, 5 stars1 week ago
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!!!
Guest favorite
The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island provides extra counter space with two black stools positioned nearby. The open layout allows a view of the adjoining living area through a doorway.
Condo in Chicago
4.91 out of 5 average rating, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars6 days ago
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!
Guest favorite
A bedroom features a spacious bed with neatly stacked towels at its foot. A mural depicting a baseball player stands on one wall, complemented by a nearby mirror and door. The room is designed with light wood flooring and sports-themed decor.
Condo in Wrigleyville
4.84 out of 5 average rating, 431 reviews

Authentic Condo steps from Wrigley Field!

KellyRating, 5 stars2 weeks ago
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?
Top guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Lake View
4.98 out of 5 average rating, 118 reviews

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

RebeccaRating, 5 stars3 days 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!
Top guest favorite
A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.
Condo in Chicago
4.92 out of 5 average rating, 346 reviews

Susie's Space. 2BR easy parking & pet friendly

MatthewRating, 5 stars2 weeks ago
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.
Guest favorite
A spacious living area is arranged with a large sectional sofa facing a wall-mounted television. A decorative area rug lies beneath a low coffee table. Adjacent, a dining area features a wooden table surrounded by chairs, with an open kitchen visible in the background.
Condo in Near North Side
4.99 out of 5 average rating, 137 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

MohamedRating, 5 stars3 weeks ago
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.

Quick stats about vacation rentals with outdoor seating in Wicker Park, Chicago

  • Total rentals

    90 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    6.5K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

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