
Vacation rentals with outdoor seating in Wicker Park, Chicago
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Top-rated outdoor seating rentals in Wicker Park, Chicago
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House rentals with outdoor seating

Flat in Lincoln Park 2-Flat Central to Everything
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 !

ALOHA Penthouse in Wicker Park w/Backyard Patio
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.

Chicago River House -BBQ Oasis now open!
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.

Unique porcelain-enamel paneled "Lustron" home
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.

Cool Quiet Coach House, Private Access + Patio
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!

Retro Modern Bungalow (fire pit • free parking)
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.

Wrigleyville Southport Studio
Great little hideaway to rest and recharge after being out in the city all day.

Cozy/Spacious WFH Family Friendly w Permit Parking
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

Bohemian Moto Inn
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.

Modern Apt with style & comfort in Pilsen Chicago
Awesome spot. Highly recommend it!

Bright two bedroom garden apartment
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.

2nd floor of 1908 brick two-flat in Logan Square
Lovely flat, excellent collection of games and books. Very well stocked, super clean. Hosts were very friendly and responsive.

Private Garage+Laundry+Restaurant Row+93 Walkscore
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.

Logan’s Cozy Inn.
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.

2BR Bursting w/ Character in Hip Logan Square!
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!

Funky & newly remodeled 1 bed in Hip Logan Square
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

Inspired, luxe living in Logan Square on BLVD #1
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.

Logan Square Beauty with 2 Bedrooms W/parking
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.

Spacious & Modern Family Friendly North Center Apt
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.

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!

💥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!

Susie's Space. 2BR easy parking & pet friendly
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.

Modern Chicago Movie Themed Apt
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.

Welcoming 2BR in Chicago's Best Neighborhood!
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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- 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
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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