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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

Top guest favorite
Home in Lincoln Park
4.98 out of 5 average rating, 108 reviews

Flat in Lincoln Park 2-Flat Central to Everything

OlivierRating, 5 stars1 month ago
We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !
Guest favorite
A brightly colored bedroom showcases a spacious bed adorned with a vibrant duvet. Natural light filters through large windows, illuminating the minimalist decor featuring a ceiling fan and playful wall art.
Home in Wicker Park
4.9 out of 5 average rating, 203 reviews

ALOHA Penthouse in Wicker Park w/Backyard Patio

AlishaRating, 5 stars1 month ago
Liz was a wonderful host. Informative and detailed. She has literally thought of everything you would need for the stay and then some! Fully stocked cleaning supplies, toilet paper, linens and kitchen items. Very clean and neat place that allowed for everyone to have a space of their own and not feel cluttered. Thank you for such a wonderful experience.
Guest favorite
An outdoor area features a partially enclosed space highlighted by warm wood paneling and a large window. A grill is positioned against the wall, with a concrete floor leading toward a well-lit interior visible through glass doors.
Home in North Park
4.96 out of 5 average rating, 172 reviews

Chicago River House -BBQ Oasis now open!

NiccoloRating, 5 stars2 weeks ago
Loved everything about this place! I cannot say enough good things about my stay. I will say, it is quite far from Chicago. It didn’t quite matter for me as I knew I wanted to find a place away from the city but on a week day it is about an hour or so from downtown. The place was quiet, pillows insanely comfortable, amazing shower, kitchen was great and well equipped, clean washer and dryer, easy to get in and out of the place. Great place to stay.
Top guest favorite
The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.
Home in Wilmette
4.97 out of 5 average rating, 151 reviews

Unique porcelain-enamel paneled "Lustron" home

CaitlinRating, 5 stars1 week ago
This unique home was perfect for our weekend stay in Wilmette. The backyard is really pretty and private. We stayed with our two young kids, and there was enough room for everyone. Backyard is fenced in, so the kids could roam around.
Guest favorite
A striking, two-story brick house is presented with a dark facade and a prominent red door. Large windows provide natural light, while a set of stairs leads up to the entrance. The outdoor area features a clean pathway and surrounding minimal landscaping.
Home in Wicker Park
4.92 out of 5 average rating, 274 reviews

Cool Quiet Coach House, Private Access + Patio

BettinaRating, 5 stars2 weeks ago
Had a great five night stay, still only scratched the surface on what this fun neighborhood has to offer. Cute little house, squeaky clean and well organized and quiet even though close to anything you would want (including blue line). Host team super responsive, would 100% stay again!
Top guest favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.99 out of 5 average rating, 144 reviews

Retro Modern Bungalow (fire pit • free parking)

NoahRating, 5 stars6 days ago
We had a great stay at this place. The location is very nice. Get to be outside of downtown still while close enough to visit whenever you’d like. The retro vibes of the home itself is very cozy and unique. Will definitely book again if we ever come back.
Top guest favorite
A row of multi-story brick buildings is presented along a tree-lined sidewalk. Each unit features large windows adorned with decorative elements. Soft illumination from the interiors creates a welcoming ambiance as greenery frames the entrance, and a secured fence borders the property.
Home in Lake View
4.98 out of 5 average rating, 256 reviews

Wrigleyville Southport Studio

KyleRating, 5 stars2 days ago
Great little hideaway to rest and recharge after being out in the city all day.
Guest favorite
A bright open-plan living area showcases a spacious couch and a coffee table atop a colorful rug. The kitchen features white cabinets and modern appliances, with ample counter space visible. Natural light filters in, creating a welcoming and functional environment.
Home in West Town
4.97 out of 5 average rating, 127 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

Katy Rating, 5 stars1 week ago
Lovely place! Nathaniel was very responsive and accommodating to us while in Chicago! Made everything easy and created a homey space for us to enjoy. Would definitely stay again.

Apartment rentals with outdoor seating

Guest favorite
The living area features a green sofa and two accent chairs with yellow upholstery, arranged on a patterned area rug. A wooden coffee table sits in front, with soft light filtering through the large windows adorned with sheer curtains. Plants add a touch of greenery.
Apartment in West Town
4.96 out of 5 average rating, 139 reviews

Bohemian Moto Inn

LynnRating, 5 stars2 weeks ago
Surprisingly spacious apartment with a well-stocked kitchen. We brought our bicycles with us to get around downtown and appreciated being able to rent the garage spot and keep them safe.
Top guest favorite
A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.
Apartment in Chicago
4.99 out of 5 average rating, 227 reviews

Modern Apt with style & comfort in Pilsen Chicago

AlexanderRating, 5 stars5 days ago
Awesome spot. Highly recommend it!
Top guest favorite
A modern living space features a comfortable gray sectional sofa and two light-colored chairs. A round wooden coffee table sits on a patterned rug. Natural light enters through two small windows, complemented by minimal greenery in the corner.
Apartment in Wicker Park
4.95 out of 5 average rating, 115 reviews

Bright two bedroom garden apartment

AdrianaRating, 5 stars1 week ago
Carol was such a great host! She was very flexible to work with us, and any message that we sent. She was always very helpful and responsive. We would surely come again! There was so much to do around the area and so many good restaurants, we didn’t even feel the need to go downtown Except for the event that we had planned for the weekend. It was super easy to get on and off the train. The walk was 15 minutes if that. But it’s such a nice neighborhood we even considered moving there because of our stay. We really appreciated the chalkboard in the kitchenthat Carol put up for everyone to put their recommendations or favorite places there while they stayed.
Top guest favorite
A sunlit living area features large windows framed by wooden accents, allowing natural light to illuminate the space. A comfortable futon is positioned alongside an armchair and a glass coffee table on a textured rug, with a small television and simple wooden furniture completing the layout.
Apartment in Logan Square
4.95 out of 5 average rating, 514 reviews

2nd floor of 1908 brick two-flat in Logan Square

KalyanRating, 5 stars3 weeks ago
Lovely flat, excellent collection of games and books. Very well stocked, super clean. Hosts were very friendly and responsive.
Superhost
A rustic wooden table with a live edge is paired with two minimalist stools. The light-filled space features a gray sofa in the background, complemented by soft furnishings and potted plants that add a touch of nature.
Apartment in Logan Square
4.86 out of 5 average rating, 118 reviews

Private Garage+Laundry+Restaurant Row+93 Walkscore

EmmaRating, 5 stars2 weeks ago
We really enjoyed the location as its fairly close to the train, restaurants, and coffee shops. The space was great as it had all the amenities you need. We appreciated Ava reaching out to make sure check in went well. I would recommend this place to anyone.
Guest favorite
A spacious basement entertainment area features a comfortable sectional sofa and a large coffee table. A pool table is positioned in the center, while a wall-mounted TV and an electric fireplace create a relaxed atmosphere. Light-colored walls and flooring enhance the space's openness.
Apartment in Logan Square
4.86 out of 5 average rating, 109 reviews

Logan’s Cozy Inn.

SandraRating, 5 stars1 week ago
Great location with lots of nice bars and restaurants locally and easy access also to the CTA blue line to Downtown and O’Hare. Apartment was ideal and was just as described. Would recommend and if ever back in Chicago would look to stay here again.
Guest favorite
A cozy living area features an exposed brick wall, offering a rustic touch. A comfortable couch is paired with a wooden coffee table, while artwork hangs on the walls. A television is mounted above a rustic shelf, and soft lighting enhances the warm ambiance.
Apartment in Logan Square
4.92 out of 5 average rating, 551 reviews

2BR Bursting w/ Character in Hip Logan Square!

MichaelRating, 5 stars2 weeks ago
I had a wonderful stay at this Airbnb in Logan Square! The location is fantastic—nestled in a vibrant, artsy neighborhood with plenty of local cafes, bars, and unique shops all within walking distance. The Blue Line is also nearby, which made it super easy to get downtown. The home itself was clean, stylish, and exactly as pictured. The bed was comfortable, and I appreciated thoughtful touches like a stocked coffee station, local guides, and fast Wi-Fi. It was a peaceful retreat after a day exploring the city. Our host was responsive and helpful, providing great recommendations and ensuring check-in/check-out went smoothly. I’d absolutely stay here again the next time I’m in Chicago. Highly recommend!
Superhost
A modern galley kitchen features green cabinetry and white countertops. A decorative backsplash with a floral pattern complements the design. Appliances include a gas stove, dishwasher, and coffee maker, while ample shelving showcases houseplants and decorative items.
Apartment in Logan Square
4.84 out of 5 average rating, 165 reviews

Funky & newly remodeled 1 bed in Hip Logan Square

SarahRating, 5 stars2 weeks ago
Great neighborhood, clean space, easy access, stylish interior, and good kitchen. Pretty quiet for a basement apartment. Perfect for our quick stay in the city. Yes the ceilings are low and there isn't a lot of natural light, but the owners made good choices and created an open, comfortable space. We didn't see "parking on the premises", but we took that to mean that there is easy street parking in the neighborhood, and there was. The train is not that close, but there is a bus that will take you there and only a few blocks from the house. Overall, a good stay.

Condo rentals with outdoor seating

Top guest favorite
An open kitchen and dining area are visible, featuring dark cabinetry and a large island with seating. Natural light fills the space through numerous windows, highlighting a wooden dining table and a cozy seating area, accented by a plush sofa and decorative pillows.
Condo in Logan Square
5 out of 5 average rating, 100 reviews

Inspired, luxe living in Logan Square on BLVD #1

Jan M.Rating, 5 stars2 weeks ago
We loved everything about our family stay at Heather's beautiful home! A great deal of thought has been made to make this space a special place to hang out, with special provisions, a wellness-area, peaceful amenities, many special 'extras' we have not encountered at other airbnb experiences. Heather's communications before our stay were greatly appreciated, along with local information, a personal guidebook to inform us of walkable, driveable, or mass transit options for restaurants, coffee shops, grocery stores, entertainment, etc. The kitchen is a beautiful space to enjoy cooking in or bringing take out food home. I intend to book this home again, if needed for a larger group. We are a family of 5 adults. However, this space is also very kid-friendly with areas for children, strollers, raingear, highchair--anything a family might need. Our sleeping space was peaceful, comfortable, and private with so many bedrooms and 2 bathrooms.
Superhost
A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.
Condo in Logan Square
4.78 out of 5 average rating, 256 reviews

Logan Square Beauty with 2 Bedrooms W/parking

CheenuRating, 5 stars1 week ago
Very nice place. Looked professionally cleaned. Matt was prompt with his replies and managed to accomodate a late check out, which was helpful. 10 mins walk to Logan Square station where you can catch blue line to downtown.
Guest favorite
A three-story building is presented, featuring a light-colored exterior and a welcoming front porch. The entrance is framed by white railings, and large windows allow natural light to fill the interior. Adjacent buildings are visible, showcasing typical urban architecture.
Condo in North Center
4.91 out of 5 average rating, 152 reviews

Spacious & Modern Family Friendly North Center Apt

SupitchayaRating, 5 stars2 weeks ago
Justin is very responsive and helpful. We booked the place for almost two weeks, and he offered to bring us new towels. The place is nice and clean. Great location.
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 Lincoln Park
4.91 out of 5 average rating, 109 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

JonathanRating, 5 stars1 week 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!
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 stars5 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 Logan Square
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 modern living area features a large black leather couch accompanied by a sleek armchair. Artistic Chicago-themed decor adorns the walls, including a vibrant sign. Natural light fills the space through window coverings, with a stylish area rug enhancing the warm ambiance.
Condo in Ukrainian Village
4.93 out of 5 average rating, 136 reviews

Modern Chicago Movie Themed Apt

IsaacRating, 5 stars6 days ago
The house was nicely situated, tidy, and perfect for our needs. They definitely keep to the movie theme, and I liked the little porch in the back.
Guest favorite
A cozy living area features a modern sectional sofa adorned with colorful cushions and a vibrant area rug. A wooden coffee table provides a natural accent, while bright artwork is displayed on the walls. Natural light filters through the window, and the main entrance is visible.
Condo in Ukrainian Village
4.83 out of 5 average rating, 312 reviews

Welcoming 2BR in Chicago's Best Neighborhood!

NaomiRating, 5 stars2 weeks ago
My friends and I had amazing stay! Kathleen was incredibly informative, accommodating, and super responsive throughout. The place was close to everything, which made getting around so easy. We also really appreciated the abundance of bedding and towels, such a thoughtful touch. Would definitely stay here again!

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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