Pet-friendly holiday rentals in South Loop, 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 !

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

Liz was a wonderful host. Informative and detailed. She has literally thought of everything you would need for the stay and then some! Fully stocked cleaning supplies, toilet paper, linens and kitchen items. Very clean and neat place that allowed for everyone to have a space of their own and not feel cluttered. Thank you for such a wonderful experience.

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.

House is centrally located . Clean. Host was responsive. 100% recommend this property !

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!

Marc was a responsive and helpful host throughout our stay. The location was great—convenient and easy to get around. Check-in was smooth thanks to the clear instructions provided. The interior was exactly as shown in the photos: new, beautifully decorated, and modern. We had a wonderful stay and would definitely recommend this place!

For basics, it is very clean and comfortable with a well appointed kitchen, comfortable beds, and easy street parking. The space itself is remarkable. Patterned tin walls and ceilings, a triangular shape, nicely decorated, and the construction details from converting it to an apartment are all in keeping with the style. We loved it.

Rosa was a stellar host; welcoming, responsive, and thoughtful throughout our stay. Her home is absolutely beautiful, more of a cozy apartment space that's perfect for two people. The décor is tasteful, and everything was spotless and well-maintained. The bed is a queen, which can be a bit snug for someone 6'3", but we still managed to get some good rest. Overall, it was a wonderful stay and I wouldn’t hesitate to book with Rosa again in the future. Thank you!

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.

Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.

Wonderful stay! This property was perfectly located for us--right on the Red Line CTA, with access to buses and other lines. Right along the waterfront and Michigan Ave, and easy walk to downtown, museums, restaurants, Shedd Aquarium, the Planetarium, etc. The property was spotlessly clean, the beds were super comfy! Nice views from the 5th floor. There was a garage available for parking but we didn't need it. There was a small gym with 24-hour access in the building and I got a week pass without a problem. We didn't use the laundry room in the building. The weather was too cold and windy to use the roof deck but it looked nice. The owners were wonderful to work with-- very responsive and proactive. We enjoyed our stay immensely, and would stay here again in a heartbeat!

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!