Pet-friendly holiday rentals in Cook County

This wasn’t really supposed to be a “fun” trip. I unfortunately had to put my mom into assisted living, but found this Airbnb close to her home. My 2 boys came with me (10 & 13) and if it wasn’t for the fun accommodations in this house, they wouldn’t have had the awesome time they did. It was a fantastic distraction, and the house felt like a home. We loved the updated bathrooms, the modern look and feel, and don’t forget the basement! We spent lots of time down there playing putt putt and arcade games. My son even hooked up his X-Box and played (which he ended up leaving behind on accident, and the host Marc actually drove it to my moms to drop it off - A SAINT!) We will likely be back at least every couple months to check on my mom and will book here from now on!

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.

This was a fantastic stay! The space was beautiful, spacious, clean, and well located. Definitely a great option if you're in the area and need a larger space.

Simple check out instructions, clean, flexible

Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!

Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

Daughter's wedding in Naperville! Great weekend and the Nest was the perfect place to base out of for all of the festivities we attended. Precious little house and backyard which we enjoyed staying in with our fur babies. Thank you and we will definitely stay at Liz's place the next time we need to visit Naperville. : )

Rita’s place was perfect for our weekend stay!It had plenty of space, was easily walkable to the train station and restaurants, and had everything we needed. Rita was communicative and super kind. We would definitely recommend this stay for others.

Overall great for our stay, Fairly close to a lot of things.

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.

Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.

Excellent place to stay, easy access to highway, quick ride to downtown

This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

We had a wonderful stay in Chicago with our infant and toddler! The check-in process was smooth and easy, which made settling in stress-free. The apartment was clean and cozy, with fresh sheets, a spotless bathroom and bedroom. The kitchen was fully stocked with all the essential utensils made it convenient to prepare breakfast for the kids. One big plus was the parking, the detailed video provided made it super easy to find the exact location without any confusion. The location of the apartment was fantastic within walking distance to Willis Tower and surrounded by great restaurants. It was also just a short 15 mins drive to major attractions like the Shedd Aquarium, Adler Planetarium, and Navy Pier. Everything we needed was already available in the room, we didn’t have to call out or ask for anything during our stay. Overall, a comfortable and convenient stay for families traveling with little ones. Highly recommended!

This was a perfect stay for an amazing weekend getaway and Festival experience. The area was walkable and had several great options for food and bev. Free street parking directly in front of the property, secure garden level access, and all the instructions and guidance were well laid out. Additionally, they had a guidebook that was well put together and everything was cohesive and exactly as pictured and described in the app. John was very responsive, friendly, and he and his family provided a perfectly appointed environment for our getaway… And their dog, Star 🐶 was such an angel! We had a great time, thank you!

Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

This place is definitely a gem! Excellent location and spacious house for a family! We will book here again when visiting the area. Very clean, accommodating and comfortable stay!

Liz is a great and considerate host. We're able to park our car in her driveway and that was super convenient. Will definitely come back to stay.

★★★★★ We had an absolutely phenomenal stay at Nayeli’s townhouse in Hoffman Estates, and I can’t recommend it highly enough! From the moment we booked, Nayeli’s communication was top-notch—warm, welcoming, and incredibly detailed. The pre-arrival message with clear instructions for check-in, parking, and amenities made everything seamless and stress-free. The townhouse itself is a gem—spotlessly clean, stylishly decorated, and equipped with everything you could possibly need. The newly remodeled bathroom in the bedroom hallway was a delightful surprise, with modern fixtures and a fresh, spa-like feel. The master bathroom was equally impressive, and the entire home felt cozy yet spacious. The beds were super comfortable, and the futons in the basement were a great bonus for our group, ensuring everyone had a cozy spot to sleep. One of the best experiences with Airbnb I had! Thank you for the unforgettable Stay!

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

Very nice stay! In a great neighborhood, would stay again. Was everything me and my group needed!

Well kept, quiet environment. Host is responsive.

Quiet and friendly neighborhood. Very walkable. Place had everything I needed for the stay. Will definitely return if I’m ever in the area again.

Cornell was very thoughtful as he made sure we were staying hydrated in the extreme heat he was very welcoming I felt straight at home and he was also very nice and friendly which made it easier to get along with and talk to him! He is a great host and if I find myself ever coming back to Chicago, I’ll make sure to go through Cornell if I need a place to stay for the trip!