
Vacation rentals with outdoor seating in Wrigleyville, Chicago
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Top-rated outdoor seating rentals in Wrigleyville, 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 !

Duplex Home RoscoeVillage/Wrigley Free St Parking
It would be impossible to imagine a better location than this if you want to walk to coffee, restaurants, the train and Wrigley. We did all of those things, and the house was in a clean and safe, beautiful leafy neighborhood. We were two families, including three children, coming together from different cities to catch up, relax, and go to a Cubs game. House and neighborhood surpassed our needs, easy access and fell in love with Roscoe Village. Same place next summer hopefully! :)

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Unique porcelain-enamel paneled "Lustron" home
I enjoyed my stay here which enabled me to be close enough to Northwestern’s campus as I worked on a writing project. Being minutes from downtown Wilmette was a plus—be sure to check out Saint Roger’s Abbey bakery for wonderful French pastries! The house was neat, tidy, and matched the description. I also appreciated the record collection!

Entire first floor in Lincoln Square!
We spent a fantastic week in Nora’s home and it felt very much like our home for the week. The apartment was much more spacious than we expected and everything was exactly as described. We found parking easily each day and enjoyed how walkable the home was to local amenities. The drive to downtown was about 35 min, making it a convenient spot, and the chance to enjoy a real Chicago neighborhood experience. Highly recommend for other travelers, including those with families!

Retro Modern Bungalow | fire pit | free parking
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

WrigleyRoost <5 min to Cubs/train/lake!
It was a great place to stay!! We were in town for Cubs games and the location was an A+. Easy to get around, we walked everywhere without using the car the whole weekend - ballgames, bars, restaurants, grocery store, and coffee shops were all nearby. The unit was perfectly clean and well appointed. We hope to come back soon!

Wrigleyville Greystone
We had a great time staying at Mark's place. We had everything we needed, close to all the things you need, easy walk to brown line and red lines to get Downtown. The space was comfortable and well decorated, with a beautiful back courtyard to hang out in. Plus if you enjoy phones, this is your kind of place.😜
Apartment rentals with outdoor seating

Cozy guest studio, great for couples!
Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!

Executive Apartment on Lake Michigan with parking
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!

Sunny, Cozy, Colorful Andersonville
Lida's place was very clean. Even after walking around in bare feet, the floors felt very clean. It was convenient to the red line trains and only .5 miles to Mariano's grocery store. I felt very safe in the neighborhood, and Lida was very friendly. I would highly recommend staying at Lida's place.

Ravenswood Guest House Annex
We loved staying at Richard's home; He ensured my friend, and I had a great time and accommodated the space to our needs. The place was clean and feel comfy. They left clear instructions and recommendations for our stay. They even left some snacks in the fridge for us that helped us after a long trip. The home is in a beautiful, peaceful neighborhood. Richard is a kind and thoughtful host; you can tell she cares about the people, and that makes a huge difference when it comes to picking a place when you are traveling!.

Spacious 2 Bedroom in the heart of Lakeview!
Terry's place is spacious & looks just like the pictures. Terry's place was clean & had all needed amenities. Great location in Lakeview to get to shops/stores/restaurants, and also super easy to get to downtown Chicago.

Stylish Comfy Flat by Wrigley Field+CTA for Groups
Great location and very nice place. Had a great stay.

2BR Bursting w/ Character in Hip Logan Square!
Had a great stay! The location was perfect, close to tons of restaurants and bars, and just a short walk to the subway. It only took about 20–30 minutes to get downtown. The host was super responsive and went above and beyond with some amazing local recommendations. She was also really accommodating with luggage storage options both before check-in and after check-out, which made things so much easier. The apartment had everything you’d need for a short stay, including a full kitchen and a fantastic shower. I’d 100% recommend this place and would definitely stay here again!

Brand new 2 bed 2 bath apartment in Lincoln Square
The house was exactly what we needed. A nice peaceful place and nearby lots of great parks and restaurants. Perfect for my family with a toddler.
Condo rentals with outdoor seating

Designer Lakeview Haven. Private Rooftop Oasis!
Staying at James' place was a dream! 😍 His home was clean, spacious, comfortable and had everything my partner and I needed. We adored the balconies and the rooftop deck was very cool! We loved that his home was very close to one of the Brown Line stations and we could hop on the 'L' very quickly. We also ate at Frasca, Avenue Tap & Kitchen and Bitter Pops and the food was excellent! We would stay here again!

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

Spacious & Modern Family Friendly North Center Apt
My husband and 2-year-old stayed here with my parents during a family reunion. We appreciated the kids books and toys, the crib and especially the big closet in the bedroom where we could shut the door when we put the kiddo down early. Spacious and comfortable place that we enjoyed staying in.

Susie's Space. 2BR easy parking & pet friendly
Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!

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.

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!

Luxury 4 bedroom steps from Wrigley
Brian’s condo was the perfect place to have old friends and family to gather in chicago! The place was huge, lots of areas to hang out, front and back porch, and right next to Wrigley field and the red line train. Thanks for an awesome stay!

Updated Designer Duplex In Fulton Market W/parking
Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai
Quick stats about vacation rentals with outdoor seating in Wrigleyville, Chicago
Total rentals
40 properties
Nightly prices starting at
R891 ZAR before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park