Holiday rentals with outdoor seating in Near North Side, Chicago

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 !

We had a party of 6 and there was plenty of room to spread out. Each couple had their own bathroom. Families with kids can have their kids nearby at night which can be helpful with younger children. We had a large vehicle which didn’t fit through the gate but we were able to get permits for street parking each night which was readily available.

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!

Nicole and Matt were extremely responsive and excellent hosts. The bnb was in an awesome location in Lincoln Park with lots of great bars, restaurants and close proximity to the plethora of attractions in downtown Chicago. I would stay there again and recommend this lovely town home to all!

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!

Traveling for work and needed a large space for our group. Place was great and lots of places to sleep. Host was responsive when needed and clear instructions to get in. Would stay here again in the future!

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!!

Marla and James' place was cozy and perfect for our family's stay! We were out and about a lot of the day in Chicago, and the Airbnb was a perfect, peaceful place to return to. There were lots of cozy touches, like ample board games available to play, some snacks and tea bags set out, and a lovely porch and sunny kitchen table and living room setup - so multiple areas to gather as a family and relax! There are also lots of nice cafes and restaurants and other small businesses within walking distance. Would definitely stay here again and would recommend to anyone looking to visit Chicago!

lovely stay in nice neighbourhood with great bars and restaurants close by . Easy access for train to city.

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.

Loved the area! Super close to restaurants and where our daughter lives do it was a great location

From booking to check out Wendy and Matt communicated with me every step of the way. Very responsive, helpful, and friendly. The Airbnb is just as described and is absolutely beautiful, but also comfortable and homey. They have thought of everything. My husband and I both had to work some and the desk set up with extra large monitors was the best surprise! The location is perfect-walkable to some really fun restaurants. We went to Happy Camper, Small Cheval, and Mr. Gyros. The red line is right around the corner and we felt very safe walking the neighborhood after dark. You will meet many people on the street with friendly dogs :) The ability to park our car off the street was also one of the best perks of this place! Our family couldn’t have picked a better place to spend our time in Chicago. Thank you Matt and Wendy!

Highly recommend! This location was great! Listing was exactly as pictured. Parking was a BREEZE. Very walkable. Mando and Bev provided plenty of guidance and recommendations ahead of time and during the stay. They checked in on us and made our entire trip a breeze! We used public transit and the location was perfect for it. The trains are close, but far enough away you can’t hear them. In fact, the whole place was quiet, which was great. Check out is also very easy. We came with two 9 year olds and the room worked great for them. We’re already planning another stay for next year and hope this location is available!

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!

Love the location, great place for a quick weekend trip. Near all the great places in wicker park

We loved staying here during our recent trip to Chicago. We were traveling with two young children, and the space was perfect for us. We were also grateful for the parking permits that allowed us to park nearby. The location was great—the neighbor was lovely, and we were happy to be so close to Lincoln Park. Overall, we’d recommend the space!

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

Great place! Everything was clean, in a good location and they communicated well.

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 really good stay here! The hosts were super responsive and helpful, which made things easy from start to finish. The place was clean and had everything we needed. It’s also in a great spot — close to everything, which made getting around convenient.

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.