Holiday rentals with outdoor seating in North Side

Karna was very helpful with check-in and responsive to all questions. The place was very well organized and well maintained.

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.

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!

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!

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!

We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.

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

This is a cozy apartment that is perfect for families, close to a great neighborhood and a nice walk among historic homes to the CTA. Charles was extremely helpful and courteous throughout the entire process. The apartment was very clean and inviting with 3 small but separate bedrooms. I definitely plan to reach out to Charles again next time that I am visiting Chicago with family.

I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.

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 stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.

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

James was an outstanding host—attentive, responsive, and thoughtful throughout our stay. The property was exactly as described: clean, comfortable, and well-equipped, making our visit truly enjoyable. We felt well taken care of, and we’re already looking forward to our next trip back. Highly recommend!

Wonderful oasis from which to explore Chicago. Walking distance to the blue line (and therefore downtown and the airport), the 606, and good restaurants. Cute decor and a spacious interior that truly provides an experience that is better than a cramped hotel room. John also provided great local recommendations. Highly recommend!

My stay here was fantastic! Barry was very responsive & quickly answered any questions I had throughout our trip. The apartment is wonderful & truly has everything you could need inside it. It was exceptionally clean & everything was thoughtfully labeled (lights, outlets, etc) which proved to be very helpful. There was plenty of closet space in each bedroom to put our things as well as a large dresser in the main bedroom. The vanity desks in each room were great because it gave us space to get ready outside of the bathroom. Barry graciously allowed us to use the washer/dryer downstairs so we could do laundry throughout our stay. Parking was a breeze. We were provided temporary parking permits throughout our stay & never had any issue finding a space on the street to park. The house is nestled in a beautiful area & is a great location for strolling the neighborhood or walking the dog. It is also a short walk from all of the restaurants & Sunday Farmer’s Market. We would stay again!

Close to the green line for easy transportation.

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

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!

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.

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!

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