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.

We had an amazing 5-star stay in Chicago! The home was spotless, artfully decorated, and full of thoughtful touches like a piano, guitar, and a welcome gift. We loved the 360° rooftop deck with a fireplace and the fully equipped kitchen with a balcony. Beds were super comfy with high-quality, clean bedding. Though close to downtown, the home is on a quiet street and offers keyless entry — very convenient. We also appreciated the private garage with EV charger, 3 TVs, 2 fireplaces, and a great Nespresso machine. The location is unbeatable—near top spots like Swift & Sons and City Winery. Natasha was an excellent, responsive host. We’re already planning to return!

Mike’s place was great, and he was quick to respond to questions. Check in was easy, and there was plenty of street parking out front. It was conveniently close to walk to restaurants and shops. Our pup loved the backyard too. Would love to stay here again sometime.

Thank you so much, Matthew! The beds were comfortable, the BNB was extremely clean, but still felt the coziness of Home. The hot tub definitely was the highlight of our wind down at night. We will be booking again!

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! :)

Our stay at Megan's place was awesome! Very cute apartment in a great neighborhood with all the amenities you could ask for! Megan was a great host! Will definitely stay here again when visiting Chicago!❤️

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

Very spacious, great neighborhood, fun amenities, great backyard, excellent bedding and pillows!

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.

Couldn’t find a better spot for me. I’m from LIlINCOLN PARK Chicago. I go every year for my birthday, right in the heart of things with a great view, very clean. The set up in the apartment was awesome. Will be back.

Absolutely wonderful stay! The place was spotless, beautifully decorated, and had everything we needed for a comfortable visit. The host was thoughtful in making check-in easy. Although we didn’t travel with children the park across the street would be an added plus for families with children (soccer field, skate board ramp, playground & tennis courts). The neighborhood felt very safe and family-friendly! We felt right at home and would definitely stay here again. Highly recommended!

Great apartment within a few blocks of everything Chicago has to offer. Large bedrooms, kitchen and living room. Beautiful views from a private terrace. The only down I would have is there is only one full bathroom with tub/shower; which is a little cramped. If there were more than just 1-2 people it's a lot of people in one small bathroom. Overall the unit was great! The hosts were great at assisting with a couple minor issues of internet and lighting. I would highly recommend!

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!

Great place. Great location. Patty was great at communicating whenever we needed anything.

Great place to stay. Paola was a wonderful host and communicated very well. Would definitely stay here again!

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 !

Highly recommended.... House was a really nice spot to stay at.... If ever back in town I'll definitely book back with them....

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.

My family and I had a fantastic stay! The space was exactly as described; clean, stylish, and thoughtfully designed. Check-in was smooth, and Adam was super helpful throughout our visit. We especially appreciated the backyard for our dogs . The location was perfect. It was close to everything we needed but still quiet and peaceful. Would absolutely stay here again and highly recommend to anyone visiting the area!

Nice clean house in a well kept neighborhood and Richard was very responsive and helpful during my stay.

A great spot!! A friend and I were in town for a concert and this place was perfect! The patio was really cool and Tom has the cutest dog!!