Pet-friendly vacation rentals in Near North Side, Chicago

We had a great experience staying with Dustin! He was helpful and attentive when we had questions, and even let us check in a few hours early to accommodate travel schedules. The house was perfect for a large group and in a great location. Would definitely recommend!

Kim was incredibly prompt with her response time. Everything was as promised and the stay did not disappoint one bit. 5 out of 5 stars Kim. Thank you for being such a great and attentive host.

Vytautas is a very welcoming, responsive host. He responded quickly to questions about the property and my stay in particular. The property is very convenient to Naperville and highways connecting to the greater area. It was easy to enter the front door and the home was toasty warm on a cold Chicago night when I arrived. It was great to have the private back yard with my dog. I think it would be fun to be there in summer when the trees have leaves and the weather is warm. The only down side for people who want to have meals there is that you have to set up a table (which is folded up in the back room) and chairs to have a group sit down. This wasn't a problem for me because I have family in the area and went to their homes for meals. And I believe the table would be large enough for 6 if you have that many people. I wouldn't hesitate to stay there again. Thank you, Vytautas

Great host, nice peaceful home with old-fashioned feel. We even met some friendly neighbors. Rich always responded promptly to questions & was overall kind & accommodating. We enjoyed the area, including many historical homes, local restaurants (DeMar’s😋) and a beautiful event at the iconic Lyric Theater. Thank you!

Very nice and comfortable home. We found it clean and it had everything we needed. Communication was great. Location work well. Could not hear the freeway hardly at all. Very cosy.

Most amazing place to stay 5/5 would recommend.

Had such a great time in Chicago at this spot! Perfect for us and the dogs. It is a great neighborhood to take the dogs walking in and the house is so cozy. We didn't want to leave! Thanks.

Great place to stay. Vic texted several times to check if we needed anything and would respond within minutes if I sent a text. The bottle of wine they left for us was a nice way to unwind after driving all day. Hope to be back soon.

We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

This was such an amazing stay! The location is perfect and within walking distance to everything. They offer free parking right on site. Everything was easy to find. The staff were super nice, and the host was quick to respond. The have plenty of toiletries as well. The gym was amazing. I was able to keep up my workouts during my vacation. I peeked in the pool, it was nice and clean. I will be staying 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.

This property has a great location in Chicago. It is walking distance to a lot of restaurants, theaters, and bars. Public transport is easily accessible and ride share is as well. The property itself is lovely. There is a doorman 24/7 and secure access to the units. The place has lots of natural light, two great bedrooms and bathrooms, and a very nice kitchen. Would absolutely stay again should we find ourselves in Chicago.

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

We had an enjoyable weekend in Chicago. Due to the cold weather, we spent more time in the rental than we had anticipated and it was so very relaxing. The unit is two floors with the bedrooms and main bathroom on floor 28 and then the kitchen/living area on the floor above. The view of the city was spectacular. The location was great for what we had hoped to do (walk around Millennium Park, Art Institute, Michigan Avenue and also drive to Science and Industry Museum and the Pullman District). The instructions from the owners were very detailed. We only had one issue with getting the thermostat to run as expected (the apartment was at a comfortable temp so heat was working, just not according to the thermostat) and the owners were very prompt at helping trouble shoot and sending someone over to look at it.

Was as described, nice & cozy! Bathroom is nicely updated with space for shower items. Ample kitchen storage. Welcomed our furry family member. With a responsive host! Thanks!

what a fun place! loads of character, beautiful surroundings, and stocked full of fun activities

Great place and host. One thing to be mindful about is the parking. Street parking is for residents with permits Monday through Saturday from 7 am to 7 pm. Ended up getting a $75 ticket.

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.

Kaye's place might just be the coziest and cutest place to stay in Chicago. Close to what you need, walkable, cozy for dogs, great taste in design, and affordable. Made my trip to the dentist a little easier to take! Thank you, Kaye- don't change a thing about your space.

When unexpected circumstances brought my family and I to Chicago, Chris and Danny’s home was a peaceful respite despite them. Their beautifully designed, impeccably clean home was an oasis. Equal parts cozy, equal parts practical. The home was well stocked, meeting all the needs you can think when staying somewhere for a month. They were also extremely kind and responsive during our entire stay, answering any questions we had and providing excellent neighborhood suggestions for cafes and shopping. If you have the privilege of visiting Chicago, I would could not over-recommend how lucky you would be to stay in Chris & Danny’s beautiful unit!

We had a wonderful experience with our 2 pups. We had an amazing feeling of being at home almost immediately. We were comfortable, safe, and enjoyed the neighborhood walks with our dogs. The yard is a comfy space for relaxing. Shopping, restaurants, walking trails, and other entertainment were near enough to be convenient, yet we were located in a peaceful area. The hosts were readily available for any questions we had and were so nice. We know we may be back in the area in the future and we are excited to know these hosts and this space exists for another visit! We are grateful for the experience we had. -Susan and Debbie

Great stay! Steve was great and accommodating! Felt right at home!

The home was exactly as described. The home was spotless, everything worked as it should. We enjoyed keeping our car in the garage. A very nice welcome bag of goodie’s to boot.

Host was great a communicating with us. The place was very clean and had everything we needed. Location was close to numerous restaurants and bars. The L was a 5 minute walk if you want to go downtown.