Pet-friendly holiday rentals in Downtown Chicago

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.

We enjoyed our stay. Clean, nice house, and in a location convenient to everything we wanted to do. Host was very responsive when we had questions. We loved being so close to the train. Great restaurants around, and also a convenience store and Family Dollar right around the corner for anything you need!

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.

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.

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!

Michael was a great host. Very responsive and friendly. The property was exactly as described. Very clean and looked just like the photos

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

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.

Had such a great stay! Everything was very clean and all information given was thorough.

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

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!

⭐️⭐️⭐️⭐️⭐️ 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!✨

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.

Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Cozy. Clean. Quiet. Charming old building. We loved the surrounding area. Lots of great places to shop and eat. Easy walk to the lake shore. Short walk to the train station. We would definitely stay here again.

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

We loved how convenient this place is to everything. The area was safe and walkable. You do have to get a key in the alleyway right around the corner but it’s not far at all from where you check in at. Front desk is nice and Claude is great at responding fast!

Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.

Well kept, quiet environment. Host is responsive.

David was super kind and helpful throughout our stay. He responds immediately and had clear instructions and communication. The apartment was beautiful and had lots of amenities. The price was also very reasonable for the location. I would definitely recommend this place to anyone!

It was really good for a small family, location the best, everything is close. Price very reasonable. I recommend to everybody.