Holiday rentals with a patio in Wicker Park, Chicago

Dean was the best host my girlfriend and I have had! He is proactive, friendly, great with communication, and provides everything you need for a great stay. Not only this, but the place was extremely comforting and beautiful! We had an amazing stay and would love to stay here again! Not to mention this place is an amazing price for how nice the stay was! Thank you Dean! You rock😎

The place was beautiful and exactly as pictured. Location-wise, I found myself out-and-about and never felt the desire to stay in the area, but it is really near the train station. Hanna and Mark are also very responsive and proactive in making sure that everything is going well. Secured, indoor parking was also very nice, and we fit a minivan without issue. Definitely recommend to anyone considering this place!

Cozy and great place! The neighborhood is quite safe and very close to 606. The rooms are spacious and clean.

Fantastic stay, perfect for the events we had lined up. Would definitely stay again.

Really enjoyed my week-long stay. The apartment is in a quiet neighborhood within easy walking distance of the metro, lots of restaurants, cafes, and groceries. The space is nicely furnished with plenty of storage space and a well-equipped kitchen. The WiFi was solid - I was able to attend Zoom meetings and a 2-hour online class without issue, not to mention streaming shows to my iPad. The walls are a little thin, so there’s quite a bit of noise from folks walking on the level above, dogs barking, and trash pickup, and the place can be a little chilly at times. Otherwise, no complaints! Irena was communicative and helpful. I’d definitely stay here again.

Carla's place was as described! Will book with this host again!

Serg is an amazing host and his team for maintenance was extremely responsive. The area was close to Chicago and clearly undergoing gentrification but across the street from a firehouse which surprisingly was not loud at night or during the day. Great rooftop views and the apartment itself was spotless and magnificent. While not many high end restaurants due to being 5 minutes outside of the city. Great stay and great value.

A great stay for my family as we celebrated a graduation! Big, exactly like the description, and Rob was very responsive and prompt! Would stay again

Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!

Such a great place to stay

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

Very responsive. Had a wonderful stay, just as advertised. Great neighborhood

This was our second time staying here, and everything was as comfortable as the first time. We highly recommend this place.

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!

My boyfriend and I had a fantastic weekend at Gladys’ place. She was super responsive, and check-in was easy with clear instructions. The apartment was cozy and modern, but still felt homey—like our own space for the weekend. It was clean, well-kept, and had thoughtful touches like a Brita pitcher, fresh towels, sheets, and a stocked kitchen. The layout was cute and the decor was simple but perfect—more personality than a hotel room without being cluttered. One of the highlights was the bus stop literally 10 feet from the door, which made getting into southern Chicago (via bus to the Blue Line) super convenient. We also loved walking to Dunkin’ each morning once we realized how close it was. The location felt peaceful but still had a few cute restaurants nearby. We never ran into the hosts, but it felt private even with the shared entry. This stay is in our top 5 Airbnbs—perfect for a couples getaway! Thank you, Gladys, for being such a thoughtful host!

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!

A Designer’s Dream – Absolute Perfection! This home is truly exceptional—every detail reflects thoughtful design and top-tier quality. It’s a designer’s dream, with stunning décor, a comfortable and beautifully clean space, and every amenity you could possibly need. The furnishings and finishes are stylish and well appointed, making the entire experience feel luxurious and relaxing. But the real showstopper? The backyard! It’s like a second living room—lush, tranquil, and designed for ultimate comfort and enjoyment. We loved spending time out there and honestly didn’t want to leave. It's so much better than anything a hotel could even begin to provide! We will absolutely be back!

When we were first looking for a place to stay, none of the available AirB&Bs looked great. A week later, we looked again, and suddenly Julia's place popped up. It was so much better looking, and with a fairer price, than any others I could find in the list. A two-bedroom that is a *real* two-bedroom, for the price that others were charging for a pull-out bed in the living room. It was just as beautiful in-person. We felt immediately at-home and comfortable. I'm someone who has insomnia, especially while traveling, but there, I had no problem sleeping somehow. Also, it truly is a short walk to the Blue Line, or even a just few steps from the 77 bus route, which goes to the Blue Line, or all the way right into downtown Chicago.

Tom’s place was exactly what we needed for a weekend in Wicker Park! The location was perfect to enjoy restaurants and stores, and the ease of access with the keypad was great for check-in and coming/going. The unit was very clean and spacious, and having a dedicated parking spot was amazing! Would definitely stay here again.

Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.

We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!

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!

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!

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.