Pet-friendly holiday rentals in Downtown 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.

Staying at Kim’s was fantastic! This house is beautiful and was the cleanest place I have stayed. There are plenty of restaurants and activities within walking distance and so many just a short drive away. I could tell a lot of time and thought was put into this house. Everything I needed was already available and even things I didn’t think about which was very nice. She was very timely with all of her responses and helped me with any questions I had. I cannot recommend Kim’s house enough! I look forward to hopefully staying here again on future trips to Chicago.

Vito had champagne and chocolates waiting for us for our New Year’s Eve stay! He was very thoughtful and the house was great!

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.

Our stay was wonderful! Very relaxing. Very peaceful and quiet neighbor. Amazing back yard. Tom is so kind and accommodating. Thank you so much for letting us stay at your home.

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.

My family of four (two kids) stayed here for a few nights before a flight at Chicago O’Hare. We really enjoyed the comfortable home and slept well! Jill was so kind and helpful. We really loved the area as well- walkable to a super cute street of shops and restaurants! We also appreciated the garage and felt very safe. We would stay here again!

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.

Absolutely perfect. Beautiful and tastefully decorated. Loved the quietness. Host was so responsive. Definitely recommend.

Great location great host will stay here again.

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!

I had an incredible stay at Paola’s place! From the moment I arrived, they went above and beyond to ensure I was comfortable and had everything I needed. The space was spotless, beautifully decorated, and equipped with all the essentials (and then some!). What really stood out was Paolas’s hospitality. They were incredibly responsive and even accommodated a late check out for us! It truly felt like a home away from home. I would absolutely stay here again and highly recommend this place to anyone looking for a welcoming and hassle-free stay. Thank you, Paola, for making my trip so enjoyable!

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.

Kaye was a great host! apartment was as advertised, bonus that she had coffee pods, bottled water and some snacks. we were in town to visit Loyola, which was an easy walk. convenient to train, as well. street parking is tricky if you come in late, but that is typical for the neighborhood. would definitely stay here again!

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!

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

Absolutely loved my stay, felt right at home. The place looked just like the pictures ! It was in a very great location surrounded by plenty of things to do and plenty places to eat ! I would definitely stay there again ! The host was very helpful & responsive he replied very quickly when needed ! 5 stars across the boards !

Place was exactly as described. As my trip was for helping my sister move house, it was a really busy few days. So, I greatly appreciated the coffee and snacks you provided. Thank you.

This home was very nice!! I was very shocked at how well it looked and how well it was maintained. Clean and spacious. The beds were very comfortable. I definitely recommend as a stay and will consider the place for my next visit.

Great stay for two months while we shopped for an apartment in Chicago. The location is fantastic—walkable to tons of restaurants, bars and the L. And Wendi's apartment was fully stocked, from kitchen to bathroom, with the things we needed to feel at home for two months.