Pet-friendly vacation rentals in Chicago

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.

Fantastic stay in Chicago! The location was perfect and easy to find, with a spectacular view of Lake Michigan and the Sears Tower. It’s an amazing starting point for sightseeing on foot with the family. Check-in and check-out were super easy, and the host was very responsive with great tips for the area. We would absolutely come back anytime!

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

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.

⭐️⭐️⭐️⭐️⭐️ An unforgettable stay in the heart of the city! This Airbnb was absolutely amazing! The location couldn’t have been more perfect right in the middle of everything, with easy access to restaurants, shops, and public transportation. The space was spotless, beautifully decorated, and felt like a true home away from home. Our host went above and beyond to make sure we had everything we needed. Their hospitality, local tips, and quick communication made our stay even more enjoyable. You can tell they genuinely care about their guests’ experience. If you’re looking for a comfortable, stylish place to stay with an incredible host in Chicago, look no further. We’re already planning our next trip back!✨

Had a great experience with our stay. The host was very communicative and friendly with their response. The view is impeccable and the location was perfect.

We had a lovely stay at Mike’s Coach House. I was able to enjoy moments in the backyard with a friend and my pup. We felt safe and at peace staying here. Hope to have the chance to stay here again!

We had a fantastic stay at this beautiful apartment in Chicago! The space was spotless, stylish, and incredibly comfortable-exactly as pictured. The building felt secure and had great amenities, and the location was perfect for exploring the city. Highly recommend and would absolutely stay here again!

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.

Loved our stay at Arturo’s place. The location was super convenient and only a 10 minutes walk to the red line. We were able to grab coffee and food within a 5 minutes walk. We will definitely stay again if we’re in town.

Clean and cozy home with a friendly host!

A great property, easy enough to get in and out of the city! The hot tub was an added bonus!

We thoroughly enjoyed our stay at Josh’s place in Andersonville. It was perfect for our large gathering with the expansive and well decorated house and a backyard large enough for family lawn games. Great location for the midsummer festival in Andersonville. Very clean and comfortable beds.

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!

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!

Wonderful house for our group of 10 ladies! Blaine was great and prompt with all communication. Would definitely stay again and recommend to others

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.

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!

We had an excellent stay here. hosts went above and beyond to make sure we had everything we needed. beautiful house and parking spot was ideal.

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.

Tom's place was really nice and exactly as described. The backyard was perfect for our pup and the neighborhood was really nice to take him on the walk. We would defintely stay there again if we are in the area.