Vacation rentals with outdoor seating in Wrigleyville, Chicago

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Popular amenities for Wrigleyville, 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 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, 291 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

FrancesRating, 5 starstoday
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! :)
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, 174 reviews

Chicago River House -BBQ Oasis now open!

ThomasRating, 5 stars2 weeks ago
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!
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, 154 reviews

Unique porcelain-enamel paneled "Lustron" home

JulietRating, 5 stars3 days ago
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!
Top guest favorite
A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.
Home in Lincoln Square
4.98 out of 5 average rating, 116 reviews

Entire first floor in Lincoln Square!

CaitlinRating, 5 stars2 days ago
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!
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, 146 reviews

Retro Modern Bungalow | fire pit | free parking

JenniferRating, 5 stars1 week ago
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!!
Top guest favorite
The building displays a classic architectural design with detailed stonework. A small set of steps leads to the main entrance, flanked by decorative planters. The surrounding fence and sidewalk provide a distinct urban context, with additional neighboring structures visible in the background.
Home in Lake View
5 out of 5 average rating, 62 reviews

WrigleyRoost <5 min to Cubs/train/lake!

BradRating, 5 stars3 weeks ago
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!
Top guest favorite
The living room features a spacious sofa complemented by decorative pillows and a wooden coffee table. A reading lamp provides soft lighting. A wall art piece with a 'W' symbol and stars is displayed above the seating area. Natural light enters through the windows, framed by wooden trim.
Home in Lake View
4.95 out of 5 average rating, 192 reviews

Wrigleyville Greystone

BeckyRating, 5 stars4 days ago
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

Guest favorite
A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.
Apartment in Maywood
4.92 out of 5 average rating, 101 reviews

Cozy guest studio, great for couples!

BrittanyRating, 5 stars1 week ago
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!
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
4.89 out of 5 average rating, 176 reviews

Executive Apartment on Lake Michigan with parking

JoshuaRating, 5 stars2 weeks ago
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!
Guest favorite
A cozy living area features a large sectional sofa adorned with colorful cushions. A glass coffee table and an accent chair complement the space. Natural light filters through sheer curtains, highlighting the artwork on the walls and potted plants strategically placed in the room.
Apartment in Andersonville
4.96 out of 5 average rating, 312 reviews

Sunny, Cozy, Colorful Andersonville

PeggyRating, 5 stars2 weeks ago
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.
Top guest favorite
A gated entryway is visible, featuring a wooden fence painted in a neutral tone. The gate is partially open, leading into a green space lined with trees and plants. The house entrance is seen in the background, with a clear sky above.
Apartment in Edgewater
4.92 out of 5 average rating, 434 reviews

Ravenswood Guest House Annex

AliciaRating, 5 stars1 week ago
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!.
Top guest favorite
A spacious living area is furnished with two leather sofas, a coffee table, and a decorative rug. A television is mounted above a tiled fireplace, and large windows allow natural light to fill the room. A comfortable armchair is positioned near the window.
Apartment in Lake View
5 out of 5 average rating, 121 reviews

Spacious 2 Bedroom in the heart of Lakeview!

PatRating, 5 stars1 week ago
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.
Superhost
A dining area features a round table surrounded by black chairs atop an area rug. Soft lighting is provided by a contemporary chandelier. A well-furnished living room can be seen through an archway, showcasing comfortable seating and natural light from multiple windows.
Apartment in Lake View
4.83 out of 5 average rating, 330 reviews

Stylish Comfy Flat by Wrigley Field+CTA for Groups

BrianRating, 5 stars1 day ago
Great location and very nice place. Had a great stay.
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, 554 reviews

2BR Bursting w/ Character in Hip Logan Square!

LuisRating, 5 stars2 weeks ago
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!
Top guest favorite
A cozy living room features a blue sofa and a brown leather armchair. A coffee table sits between them, while a large TV is mounted on the wall opposite. The room is decorated with various framed artworks and photographs, enhancing the visual interest. Natural light enters through two windows.
Apartment in Lincoln Square
4.97 out of 5 average rating, 107 reviews

Brand new 2 bed 2 bath apartment in Lincoln Square

AnnaRating, 5 stars1 month ago
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

Guest favorite
A bright living area features a comfortable dark blue armchair and a spacious gray couch. A glass coffee table sits in the center, with a decorative plant displayed on it. Large windows provide natural light and a view of greenery outside.
Condo in West Lake View
4.98 out of 5 average rating, 107 reviews

Designer Lakeview Haven. Private Rooftop Oasis!

RachelleRating, 5 stars4 weeks ago
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!
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, 110 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

NicolasRating, 5 stars1 week ago
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.
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
4.92 out of 5 average rating, 154 reviews

Spacious & Modern Family Friendly North Center Apt

JuliaRating, 5 stars1 week ago
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.
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, 348 reviews

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

RachelRating, 5 stars4 days ago
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!
Guest favorite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Condo in West Town
4.98 out of 5 average rating, 165 reviews

Spacious 4 Bedroom Condo

ScottRating, 5 stars1 month ago
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.
Guest favorite
A spacious living area showcases a light-colored sofa paired with dark green accent chairs. A glass coffee table sits atop a patterned rug, while decorative elements, including candles and potted plants, are arranged on a wall shelf. Natural light enters through large windows.
Condo in Logan Square
4.93 out of 5 average rating, 105 reviews

Wicker Park/Bucktown condo with large balcony

ErinRating, 5 stars1 month ago
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!
Top guest favorite
A modern living area is displayed, featuring a gray sofa with a yellow patterned pillow. A marble coffee table sits in front, accompanied by a comfortable armchair. A dining area with a table and chairs is visible, alongside a decorative green wall and framed photographs.
Condo in Wrigleyville
4.99 out of 5 average rating, 158 reviews

Luxury 4 bedroom steps from Wrigley

ZachRating, 5 stars2 months ago
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!
Guest favorite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Condo in West Loop
4.96 out of 5 average rating, 231 reviews

Updated Designer Duplex In Fulton Market W/parking

NicoleRating, 5 stars4 weeks ago
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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