
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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Popular amenities for Wicker Park, Chicago outdoor seating rentals
House rentals with outdoor seating

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

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.

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!

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!!

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

Beautiful Chicago Greystone
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

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

Large sunny 3BR apt. in downtown Oak Park
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.

Spaulding Oasis on 4 lots In Humboldt Park!
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

A Stones Throw from U Chicago South Campus!
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!

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!

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.

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.
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
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- The Field Museum
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- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
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- The 606
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