Pet-friendly holiday rentals 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 !

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 enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

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 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!!

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

We had a fantastic stay at this beautiful stay in downtown Chicago. The views were absolutely incredible! The home gave us a breathtaking look at the city skyline, day and night. The location couldn’t have been better, as it was right in the middle of everything, with restaurants, shops, and attractions all within pretty good walking distance. The unit itself was spotless when we arrived and had everything we needed. The bed was super comfortable, and the space felt both modern and welcoming. It was the perfect spot to relax after a day out exploring the city. The host was also very responsive and helpful!! Would definitely recommend this place to anyone looking for a clean, comfortable, and stylish stay in downtown Chicago. We’d happily stay here again!

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.

Excellent place to stay, easy access to highway, quick ride to downtown

This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

Kevin and Kayla’s unit on W Diversey Ave was a cozy and convenient spot for our Chicago trip. The space was clean, well-equipped, and had everything we needed, with quick access to buses and the Blue Line. The only minor downside was some occasional dog-walking noise from the unit above, but as it has already been mentioned before, it is to be expected. Mattresses were a bit wobbly for our tastes but it's a matter of preference. Overall a great, cozy place on a very convenient location in Chicagoland. What really stood out was Kevin’s excellent hosting—he went out of his way to make us feel at home, regularly checking if we needed anything, and was quick to help in-person when we had a small hiccup on our last day. Super responsive and friendly and a true host!

Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.

Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

My family and I enjoyed Randy's place; it was clean and well maintained. The location is a short walk to a street with multiple restaurants, shops, and bars. I felt safe walking around, even at night. There is a subway stop a short walk from the property also. A couple of other nice items to note: 1. The property has a washer and dryer with detergent supplied. This came in handy. 2. There were two premium streaming services provided. HBO and Cinemax I think.

We stayed at Reggie’s place for Memorial Day weekend as a family of 5 (2 Adults, a 4 year old, twin 2 year olds). Reggie was very easy to communicate with from the first booking request. He let us know that there couldn’t be loud noise after 10 am (no issue for us) before confirming the booking. We had no issues with check in or check out, and he was responsive to every question. The location was perfect and walkable to so many things, including all the restaurants in west loop and worked well for our family and dog.

Lovely large apartment with a nice patio for enjoying the outdoors. Beautiful and walkable area with some nice places nearby—recommend the coffee two doors down and the Armitage Alehouse two blocks south—fantastic food and beer/cocktails! Very comfortable bed! Clean, stylish and comfortable.

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

Great place to stay while visiting inner Chicago with a small dog. Easy check-in and check-out, responsive host. Parking garage and small green space nearby as well. Would definitely recommend.

We had a wonderful stay at this Airbnb! The space was perfect for our whole family—spacious, clean, and very comfortable. It had everything we needed to feel at home. The host was incredibly helpful and responsive, always willing to accommodate any needs or questions we had throughout our visit. The location was also great—easily accessible to a variety of activities, restaurants, and attractions in the area. We truly enjoyed our time here and would definitely stay again, especially with a large group. Highly recommend!

This is the perfect stay if you are looking for a place in Lincoln Park/Old Town area. Unbeatable location - walking distance to everything you could want. Plus, it is on a private street with lots of parking, even on a weekend in the summer. The apartment itself is so charming with plenty of space for a group of five. Very well stocked with everything you could need for a long weekend. Would absolutely stay here again!

Great spot in a fantastic neighborhood. Location can’t be beat. Clean and exactly as the photos looked. Thank you!!