Pet-friendly vacation rentals in Chicago

Nice appartment in West loop, well equipped and the access to a gym & pool is a plus. Cloud9 staff was responsive and helpful.

Really enjoyed my stay!! Great backyard if you have a dog or want to sit and enjoy the weather

It was a great place to stay definitely felt like home! I went for the weekend and the restaurants around there were great. They communicated very well when I had questions and responded with good time. Thank you and I’ll see you next year! :)

David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

Incredible place! Location was perfect with easy access to public transportation and great food. Host recommendations were immaculate and responsive+kind. Plenty of extra blankets pillows and towels, the jacuzzi was really nice, and the bathrooms were spotless. Very easy check in and check out process. Had almost no problems with any amenities. The smart thermostat did keep setting itself to 75 degrees or more during the night even after we set it low before sleep. Quite uncomfortable to sleep through. And the listing stated 5 beds with 2 air mattresses but there was only 1 air mattress, making a total of 4 beds. Not a huge problem but good to know for anyone who needs all 5, we didn’t. Water pressure in one shower was not great and the other drained slowly. Also some areas were a little dusty but again it was fine. Overall, this was a really really great experience and apartment. Couldn’t have asked for a better place to stay during our trip!

LOVED this studio stay. Was able to bring my dog and visit Chicago on a day trip to break up my drive across the country. Great location, clean and comfortable spot. 100% recommend

Josh's property was a great fir for our trip. I will book again when we come back out.

We had a wonderful stay - the three bedroom rental itself was amazing, and the on-site facilities (pool, sauna, game room, family room for little kids, etc.) were beyond awesome. The location is convenient as well - plenty of restaurants within waking distance, a cute coffee shop/wine bar downstairs that makes a killer caprese sandwich, and super close to public transportation as well. One of the members of our party arrived early and the friendly folks at the front desk were able to check her in early, which was an extra bonus. We’d definitely stay here again!

We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

Stayed here for my girls trip and it was a super convenient location! It was our first time visiting Chicago, and it was perfect. Had the most beautiful view we loved the private patio. Beds were all comfy and the hosts were extremely communicative the entire stay. Would definitely stay 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.

Elegant furnishings & easy check-in & check-out. Good neighbour hood

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!

The place was spectacular. The views are breathtaking. My family and I loved the place.

Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.

We had a great stay! The place was exactly as shown in the listing—clean, comfortable, and well-equipped. We had some minor issues with the digital locks, but the host was always very quick and helpful in resolving them. Overall, a very positive experience and we’d definitely recommend it!

It was amazing with the kids they enjoyed the mini golf a lot ….spacious bedrooms very good kitchen and cleaned washrooms …overall it was great

We stayed at Alix’s for one night. Our stay at Alix’s place was quite comfortable. Everything was exactly as described. We made use of the devices provided like the iron and ironing table, and the hairdryer. To my wife’s delight, the bathroom also had individually packaged makeup remover wipes! Body lotion was also provided. The air conditioning worked perfectly and we were able to sleep comfortably. Would recommend!

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.

The home was beautiful. And I love the master bedroom I felt like a queen walking into the room private bathroom. Big backyard. Everything was fabulous and next time I go back I will stay there again if available.

House is centrally located . Clean. Host was responsive. 100% recommend this property !

Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.

Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!