Pet-friendly vacation 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.

A hidden gem! We booked this for our getting ready space for our wedding. There was plenty of room for my husband and two boys to get ready in without feeling crowded. We are definitely keeping this on our list of places to stay when we are in town again.

Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.

We had an amazing stay at this gorgeous Airbnb, which ticked all the boxes for us. The property was immaculately clean and well maintained, with a lovely decor and plenty of amenities. The host was very responsive and friendly, always available to answer our questions and provide assistance. The neighborhood was quiet and residential, with a nice community feel and plenty of local amenities.

Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.

Tom provides an excellent place to stay when coming to the Chicago Ridge – Oak Lawn – Evergreen Park area. On a quiet cul-de-sac in a residential neighborhood. Easy access and everything works great.

Parking was easy, the space was clean and comfortable, and we enjoyed our stay! Michael was very responsive and helpful, and the neighbors were really nice. It was a great experience!

Everything was exactly as described. Great communication. I would definitely rent this property again.

This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.

We loved our time in Chicago. The apartment was very conveniently located. The description matched what was pictured. The train is loud outside of the apartment but I knew about this prior to booking and it didn’t bother us at all. I’d definitely stay here again.

This airbnb would be good for 2 couplesnorna family of 4. The kitchen is verynfuntional, and the living space is open and quite large. Check in/out instructions are clear. Beau was very responsive.

Definitely a great stay! October 1st and we were swimming! Decor is amazing! Tv was easy to figure out and had lots of options. We had a busy day before and after our stay so we used Michael’s pool house as a relaxing stay in between and it was perfect

Very easy for a local who needed a different place to stay during a remodel

This is a nice place to stay. We enjoyed the location and amenities.

The location was perfect for us and our kids with the park right across the street, a grocery store, coffee and restaurants all within very close walking distance! The house was very clean, everything we needed and Kevin was very quick to respond and helpful when we thought one of the kids locked us out of the house! Would definitely recommend Kevin as a host and this was a great stay!

My girlfriend and I had a weekend getaway trip to Chicago. We were looking for place to stay and found Paola’s place. We fell in love with her place. It was charming and laid-back place, in a quiet neighborhood. Close enough to walk to restaurants and explore a different part of Chicago. We loved every single minute of our trip, the house felt like home once you walked in. So grateful that Paola was able to help me and surprise my girlfriend for her birthday, with balloons, cake and a bottle of champagne. Couldn’t ask for a better host! Would definitely recommend and we will have to be back sometime soon!

I had an amazing stay at this Airbnb during my trip to Chicago. The host was incredibly responsive and accommodating.

The place was newly remodeled, very clean and organized. Everything in the apartment was well stocked and very livable, including Roku access to open your own subscriptions Hulu, Netflix, etc. Please be aware that the location is a basement with a relatively steep flight of stairs, with safety lips on the edges.

I always have the best time in Chicago, but Kaye’s place made this trip even better! I loved staying here so much, I actually extended my stay by a few days. Kaye has thought of everything, and to quote Tina Turner, she is “simply the best!” This is my favorite Airbnb I have ever stayed in and Kaye is the best host! I would recommend her place to all my friends and family. Can’t wait to visit again!

Such a beautiful home walkable to some of the best restaurants and bars in Chicago, highly highly recommend staying here! We brought our 1 year old and it was the perfect home for us to feel at home.

it was a very good stay the place was exactly as described and the beds were very comfortable! The only comment I would have was regarding the staircase getting into the apartment which was very narrow and difficult to drag suitcases up! While this was not really an issue for us I would suggest mentioning it in your listing so that in case elderly people come they know what to expect. Overall great stay!

This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.

What you pay is what you get. We didn’t come to Chicago to cook, so kitchen wasn’t an essential part of our amenities. Aside from that, it’s the best bang for our buck. The hosts are lovely people and I would come back to this place again! Loved it

Wendi’splace was perfect for an extended style stay. Very convenient location with plenty of available free street parking. The quick and easy access into the unit was a plus. Would stood up for me is how cozy but how plentiful all of the amenities were all supplied. She has gone above and beyond to stock everything that you would need to feel like you can actually live there. From a cozy couch to a kitchen table to the coffee maker, the laundry, the full size kitchen, everything else in between it was very accommodating. Wendi is an extremely responsive and pleasant host anytime I needed something. She responded right away and took care of things. Some minor things to consider is that this is the garden unit and at certain times you might hear a little bit of upstairs walking around. If you happen to have AT&T cellular service, it’s not the best received, but I was able to find some workarounds. Overall, it was a fine experience and would return!