Pet-friendly vacation rentals in Downtown Chicago

It was amazing with the kids they enjoyed the mini golf a lot ….spacious bedrooms very good kitchen and cleaned washrooms …overall it was great

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.

Highly recommended.... House was a really nice spot to stay at.... If ever back in town I'll definitely book back with them....

This place was exactly what I needed after an Airbnb host canceled on me last minute. I booked Tiffany’s place at about 6:30pm and was able to check in immediately! Place was very clean and perfect for my group of 7. There was also no cleaning instructions, Tiffany’s cleaners do it all! I will be staying here again. Thank you Tiffany!

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!

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!!

Stayed here for my girls trip and it was a super convenient location! It was our first time visiting Chicago, and it was perfect. Had the most beautiful view we loved the private patio. Beds were all comfy and the hosts were extremely communicative the entire stay. Would definitely stay 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.

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.

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!

Great place to stay. Paola was a wonderful host and communicated very well. Would definitely stay here again!

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!

The place was spotless, easy to find, and convenient. I felt right at home, and would definitely recommend to a friend or stay again myself.

The house is like a page out of an Interior Decorating magazine, an immersion experience. Like the house the grounds were equally beautiful. There was a lot of thought and love in remodeling this property. The hosts were communicative and gracious. It is located in a great neighborhood close to many dining options. I appreciated the modern touches and the cleanliness of the place. I would book this place again. Highly recommended.

It was as pictured and suited our needs. Clean and well organized. When we reached out we were responded to promptly and thoroughly. The location is good and walkable. If planning to go to Navy Pier or the Miracle Mile to go shopping (or something in that general area of Chicago), expect about a 40 - 60 min drive.

This apartment was exactly what we wanted for a week’s visit. It was spotless upon arrival and has every amenity you could need. The location is fabulous, super quiet and very secure. Claude is also a very responsive host. I highly recommend!

I had a wonderful stay! The place was exactly as described—clean, cozy, and in a great location. The host was super friendly and responsive, which made the whole experience smooth and welcoming. I especially appreciated the thoughtful touches like I’d definitely stay here again and highly recommend it to others!

Location was incredible and had quick access to almost anything. Area was quiet and peaceful to stroll through. The space was very clean and comfortable. I’d absolutely stay here again!

loved staying at Linda's place right on Madison. such a great space in a great area...my family and I enjoyed it thoroughly!

Great place, its very cute and cozy my friends and i stayed for 3 nights place was clean when we checked in, the instructions were very clear on how to enter. Parking was easy to find, Also I know in the amenities it lists that there is a blender but we couldn’t find it so we worked with what we had. Overall I loved our stay there definitely recommend booking here if you visit chicago.