Holiday rentals with outdoor seating in Wicker Park, Chicago

Great host. Very responsive and clear with instructions. Highly recommended

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.

My family and I had a great stay at Bel’s powder blue house. The house matched the pictures and description posted on the website, and was very clean and cozy inside. Bel’s communication was very effective throughout the entire experience, I will definitely be booking with him again in the future!

Great place and stay! Location is amazing!

The house is very beautiful. My family and I loved the place and how spacious it is.

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.

Michael was a great host. Very responsive and friendly. The property was exactly as described. Very clean and looked just like the photos

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!

Emily’s place is peaceful and homey, yet right in the heart of a vibrant neighborhood. Wicker Park was a nice walk from her home as well. TONS of restaurants and shopping literally a couple of blocks from her house. The train stop is a 5 minute walk away and downtown is less than a 15 minute uber ride. Emily is a very considerate and communicative host and I would stay here again. Thank you for sharing your home with me!

Rob is the best air bnb host I've ever dealt with! Very quick and helpful communication, the restaurant he recommended, Folklore, was excellent, and when we blew a fuse, he was there to get our power back on within 5 minutes! He also helped us with a later checkout AND baggage storage due to our late flight times and that made for a perfect ending to our 3 night stay. The apartment is beautifully decorated, super clean, comfortable, and in a great neighborhood that felt safe and had lots of nearby bars, restaurants, and a grocery store. And downtown was a quick uber ride away. I would highly recommend staying here and would do it again next time I visit the great city of Chicago!

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 wonderful stay. The apartment was just as advertised – clean, quiet, and comfortable. Very nicely decorated. The host provided great communication throughout. Nice location, with easy access to plenty of dining, bars, and shopping. Highly recommend!

Loved this stay! My friend and I felt right at home. Such a safe neighborhood that’s not far from local shops and restaurants. 5 star stay!!

We had a wonderful stay at Kristin’s place! She was a generous host and very responsive communicator. We traveled with our toddler and Kristin was great about providing everything we’d need, including a few toys. The primary bedroom and bathroom were both amazing, as everyone else has mentioned in their reviews. We had a very busy trip and it was great to come home to a spa-like bathroom and extremely comfortable bed each night. We will definitely be back!

We rented Larissa’s place for a weekend wedding with friends and she was very welcoming! The apartment is large and easy to share with three friends. It felt right at home when we walked in. The area is incredibly walkable and close to so many restaurants and coffee shops as well as the 606. Larissa was an amazing host and even helped us catch the blue line when we were running late by offering us a ride. We had a great time! Thank you!

We would stay here again in a heartbeat. Excellent location, very walkable, unit was bright and clean, quiet. Katherine and Dimi were very responsive … even had an iron delivered as the previous iron had gone missing. Truly can’t say enough about our stay! Thank you!

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

This is our go-to place when we come to Chicago. On this trip, our flight landed early and John was willing to let us check in a couple hours early to accommodate us. John is always very responsive, and this time around was able to work with us on an issue with the electronic thermostat (previous renter had put it in ECO mode so that it would turn itself off when no one was home). The location can't be beat.

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!

Great place for a large group to share a space. Lovely neighborhood, nice apartment, and Joe was very responsive.

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.

We really enjoyed our stay here for our first time visiting Chicago! The location isn’t too far from downtown, and the nearest CTA station is just around the corner and easy to find. The space was exactly as described, just may feel a little crammed with more than 6 people. Hosts were fantastic and easy to communicate with and gave great local recommendations.

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.