Pet-friendly holiday rentals in Chicago Loop

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 !

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

We had the best stay in Old Town! The Airbnb was wonderful and spacious for our family.

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. The place is located in a convenient location close to many shops and restaurants and just around the corner from an L station. The home was very spacious and comfy for our short stay. You can hear the train in the house however it wasn’t bothersome even for our toddlers when they were asleep.

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!

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!!

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!

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

This airbnb would be good for 2 couplesnorna family of 4. The kitchen is verynfuntional, and the living space is open and quite large. Check in/out instructions are clear. Beau was very responsive.

This place was absolutely adorable and the perfect vibe for a weekend getaway for a solo concert. Micheal was incredibly accommodating and helpful-even got me a bottle of wine and some cheese for me to really spoil myself while getting ready. She is super accommodating and helpful and the space was super cute and cozy. Hoping to stay there again soon!

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!

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!

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!

Our stay at Aaron's place was great--exactly as described, clean, had everything we needed. Great location, very walkable. Used Spot Hero for parking--lots of spots nearby. Free bagels from Steingold's for guests were a nice little amenity. Aaron was a responsive host with very quick and clear communication. Would recommend and return.

Stayed here for 2 weeks for a work trip. It feels just like staying in your own apartment. I love that they allow pets. It’s pricey (keep in mind there are additional charges for pets and for parking), but for the location and quality of the place I think it is a good value.

Very nice place, responsive host, only downside is the noise that the train creates.

I had a wonderful stay at Anthony’s place. The home was exactly as described clean, well-equipped, and in a convenient location. Check-in was smooth, and the host was very responsive to any questions I had. The neighborhood felt safe and was close to local restaurants and shops. I would definitely stay here again and highly recommend it to other travelers!

Great spot in a fantastic neighborhood. Location can’t be beat. Clean and exactly as the photos looked. Thank you!!

Great stay — very clean space with unique decor that really suited my style. The location was perfect, close to downtown Chicago and the medical district. The host was very responsive and easy to communicate with. Having a parking spot included was a huge plus. Would definitely stay again!

We were absolutely blown away by our accommodation. The apartment is even bigger and more beautiful in real life than we'd imagined from the photos. It is a very spacious apartment, equipped with two massive TVs and a very good air conditioning system. The area it's in is wonderful, with tons of eating options and things to do. We also enjoyed daily walks down to the river and Millennium Park. Mimi, who we communicated with, was very responsive and warm. We will definitely be staying there again when we return!

Great host, accommodated me and my 3 kids on a late notice and response timing was great. Home was as described , even greeted us upon arrival at 12:30 am . Hope my kids were quiet as I had little babies , it was great .