Pet-friendly holiday rentals in West Side

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.

We couldn’t have asked for a better home for our Spring Break. We last minute booked this home, and checked in 45 later but you would have never known by how welcoming Vytauta made it. Beds were very comfortable, backyard was great, we felt right at home.

Rich was a great host! Place was very comfy. I’d love to book again!

We really enjoyed our stay with our two dogs. The neighborhood is comfortable and quiet, and very accessible to the highway. Richard was great with communication and went above and beyond as a host!

Contacting Elena was easy because she was responsive. The home met and exceeded our expectations. The neighborhood is wonderful. I have recommended it to friends and expect to book again myself. Elena is a great host and again I thank her.

Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again

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.

Our family really enjoyed our stay. The parking garage connects directly to the building's elevator so very easy to unload and head up. The pool was great [same floor as this apartment] and the views were amazing. Everything was very clean. Checkout was easy too. The location is just perfect with so much within walking distance. Cloud9 was also very responsive. We'd reserve here again.

We loved our stay here! The apartment is much more spacious than we were expecting and there was more than enough storage space for our luggage. We were disappointed a bit at the poor quality of the beds but appreciated the thoughtfulness of the noise machines to aid in good sleep in the middle of the city. We would absolutely stay here again!

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.

This place is a great location for almost anything one would like to do in Chicago. Close to train lines, plenty of surrounding restaurants and grocery stores, and parking was a breeze. Also Kevin was a wonderful host and this apartment was exactly what I needed for the stay.

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!

This is probably the most value-for-money place you will find in the area. Spatious, clean and modern studio apartment, close to the park and downtown, great view on the skyline, and all for a fraction of the costs of nearby hotels.

Great location! Very walkable and safe, lots to explore in the area. Just a few blocks from the subway. Condo was clean, quiet, and very spacious and comfy beds. Just don’t plan on cooking much as the kitchen supplies (pots, pans, dishes) were quite sparse.

Staying here was absolutely amazing! The place was clean, comfortable, and so convenient for me to get to my concert and explore the city! The neighborhood is safe and quiet and there are lots of good places to eat around. I will definitely be looking here on my next visit. highly recommend!

This place was great and I would not hesitate to rebook i felt right at home the entire weekend!

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!

Had a great stay at Steve's place with my friend and our 2 dogs. Nice quiet neighborhood.

The house was very clean and comfortable. Great location and safe neighborhood. We loved having a garage! The hosts were very attentive and we will be back.

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.

Apartment is advertised: It is a basement apartment, and it feels like a basement. But it was clean, spacious, in a nice neighborhood, with good amenities, and the hosts' communications were extremely clear and helpful. Would recommend!