Holiday rentals with outdoor seating in Wicker Park, Chicago

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

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!

We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

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!!

very good location for walk to Wrigley field. felt comfortable in the surrounding area. Arlene was ready to assist with a situation we had with wife's broken hand and very Interested in her well being even though didn't meet. surprised us with a very nice 52 anniversary acknowledgement. Great host great stay

A great home base for a crazy trip. The airline destroyed our stroller, so having access to Nathaniel’s stroller made a huge difference for us. He let us know in advance about the puerto-rican festival in the area, and they were helpful letting us finish nap time for a late checkout. Even with the wild honking and partying a block away it felt quiet at night, and the dark room was good for bedtime.

Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!

Samantha’s home was clean, well kept, and had a lot of thoughtful touches, like snacks and drinks, that were really helpful when we were on the go. I also loved the dimming options for the lights in the rooms, and the bathroom had so much space and was so convenient even with more than one person using it. Samantha was also a great host who responded promptly to questions and concerns. My friend and I had a very peaceful stay here. The only down side to this location is that it’s a little far from the Loop and River North, but we knew that when we booked and were prepared. Would definitely stay here again!

This little oasis is adorable! Loved the decor and style! The main bedroom bed was super comfortable (and awesome pillows!). Everything was well stocked. I wish I could have spent more time in the home but was visiting family. The hosts were very thoughtful and had the A/C running for me before I arrived (I visited Chicago during a very hot week) so the temp was very comfortable. The hosts were very thoughtful and welcoming. 10/10 would recommend!

We had an amazing stay at Kitty’s place! From the moment we arrived, she made us feel so welcome. She even decorated the house for my fiancée’s birthday and left us treats, which was such a sweet touch. Her recommendations were super helpful and made our trip even better. The house was full of books and art that made it feel really special, and the beds were super comfy. The separate entrance was great for privacy, and street parking was easy to find, which was a big plus. Thank you so much for all the little things that made our stay unforgettable. We would love to stay here again very soon!

We had a nice 2 night stay in Chicago. Place was affordable, comfortable and clean. 10 minutes from downtown Chicago and short walk to train. Hosts were friendly and great at communication.

This was a very nice stay. It was super clean and in a great neighborhood. Thank you for hosting!

Great experience. Would stay again.

Really enjoyed our stay! We found it easy to get everywhere we wanted. If you get a chance check out Move Along Coffee a few blocks away.

Great space right next to a local bar that has the cutest dogs come by! Quiet neighborhood, and the neighbors were very respectful and nice

Kirsten & Nick’s place was lovely. The basement unit was our refreshing haven during a humid June stay. The apartment was spotless upon arrival, it was decorated so nicely with lots of extra towels, pillows, blankets & linens, etc. and the bed was the comfiest guest bed we have ever slept on. The stars of this stay have to be their absolutely adorable pets Toro🐱 and Rufio🐶. Literally the sweetest, friendliest cat and dog. If it wasn’t so darn hot outside, we would have cancelled our plans to stay in the yard and just hang out with them all day. We had a great time here. Thank you for having us Nick & Kirsten!

Great accommodations for our family of 5. It's nice to have 3 bedrooms with all queen beds so everyone has ample room. Very clean. Responsive, attentive host. Would stay here again! Thanks!

Matt is a great host. Open, responsive and informative…everything you want really when on vacation

The condo was a couple’s dream. Made you want to just live there forever. Very clean and felt like home. Hosts were communicative and courteous. Will definitely book again in the future and would highly recommend!

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.

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!

We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

The condo was very spacious and had everything we needed to stay right at home. Adrian was responsive to our questions. It was a perfect distance from the city for exploring through the day but staying in a peaceful place at night. The staircase in the house was a little steep but otherwise it was perfect.

Our stay at Kathy's cute, cozy apartment in Ukrainian Village was excellent! We would definitely book again if looking to stay in the area. Kathy was an excellent host, super communicative, friendly, and responsive! Any questions or communication to her was quickly answered. She also provided helpful information during our stay for building/facilities access and parking. Definitely a host that cares about your stay. The apartment itself was spotless and exactly as described. Rooms were a bit small, but both beds were extremely comfortable. My party of 3 fit just fine. Breakfast bars, tea, and coffee were available. All appliances and furniture were well maintained. Lots of parking on Damen Ave and nearby. Plenty of excellent restaurants and shops are available within a 20 minute walk in all directions. The Loop is pretty easy to get to via the close buses or L trains. Finally, we appreciated not having a list of cleaning demands upon checkout.