Pet-friendly holiday rentals in Old Town, Chicago

We had an amazing stay at Dustin’s place! We had a group of 9 ladies who fit perfectly with plenty of cozy beds and linens. The location was very walkable and we felt safe. We walked over to Barcocina Lakeview on Friday, and then jumped on the train to River North on Saturday to celebrate St. Patrick’s Day. We had a couple of questions during our visit, and Dustin was speedy on the replies! Everyone in the group said the experience was 10 out of 10. We hope to visit again.

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 (group of 10 women) stayed here for a weekend reunion. There were enough beds, including a few to double-up. We spent most of our time on the main floor hanging out in the front room and dining room areas. Kitchen has all the amenities (although we didn't cook much) - mostly used the fridge and coffee maker! Getting into the house was super easy for everyone since its a code access. The location is great for walking to shops and restaurants and a nearby L station.

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.

Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.

Overall great for our stay, Fairly close to a lot of things.

The location is perfect for getting to any part of Chicago. It's within walking distance of endless activities, and within one to two blocks of multiple "L" and subway lines that will take you anywhere. You are staying in the middle of the city, so you will hear the train and sirens throughout the night; however, the host provides disposable ear plugs which were very helpful. I had no problem sleeping throughout the night. Front desk staff is always friendly. The host is very responsive, and courteous. Washer and dryer in unit helped me with not having to pack as many cloths for my trip. Everything was spotless upon arrival. Would absolutely stay here again.

Great place to stay for a long time. I stayed there my entire exchange quarter and had a great time. Owners were helpful and always responsive. The place is clean and spacious and the area is safe !

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

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.

This was the perfect place to stay in Chicago! Everything was nearby and the hosts were very friendly and responsive. The amenities provided were the best part; I enjoyed the rooftop, hot tub, and the views! I will be staying here again (:

Excellent place in a beautiful neighborhood. The apartment is small but it’s great if you are just looking for a place to sleep. The neighbors is absolutely amazing with great restaurants

This place was fantastic, nice neighborhood area, with a short walk to the park! Hosts were super communicative and accommodating and it was very spacious. Would recommend!

This stay was peaceful, yet SO CLOSE to everything! My partner and I wanted a weekend getaway for his birthday, and this was the perfect place to stay. Lincoln park was a short walk away, yummy restaurants, and walking/uber distance to downtown like the Bean. The location was everything!!Caid was also very responsive which made the process stress-free.

Great space. Actually even bigger in person than what the images are showing. Superb location. Very close to restaurants and public transport as so easy. Also walking distance to the Chicago Music Exchange, if you’re a guitar player it’s the place to visit. Sam was also extremely responsive.

⭐️⭐️⭐️⭐️⭐️ 5/5 We had a wonderful stay! The space was clean, cozy, and exactly as described in the listing. The host was super responsive and made check-in seamless. We especially appreciated the little touches and great local recommendations. The neighborhood felt safe and was close to everything we needed. Would absolutely stay here again and recommend it to anyone visiting the area!

Great location, and easy access to all main streets. The neighborhood is quiet, and very safe. The people in the neighborhood were very welcoming. The condo was nice, very spacious and a great value for the cost.

Lovely space and a perfect location for exploring the city. Great restaurants within a short walk. Lincoln Park also just a short walk.

Great location, nice unit. Older building but nice updates. You can definitely hear the tenant upstairs so bring headphones or earplugs if that bothers you.