Pet-friendly vacation rentals in Downtown Chicago

This was a great stay for me and my family of 5. Our kids loved the mini golf course and enjoyed chilling on the open patio. This stay was matched everything described in the listing and was quite large. The only thing I’d say negative is that due to it being an older house not all the windows lock properly which was a major security error for me especially since it was an unfamiliar area and we had our children. Other than that no complaints ! Would stay again Thanks !

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

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.

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!

Great place for the price. Tom was a great host, always willing to help when needed. Thank you for starting the fire every night for us. Great location to have some privacy and not far from downtown. Would recommend!

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!

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.

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

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.

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!

Great place in a great location. Would definitely book again!

Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I

This was my second stay at this location, and our family had the BEST time! We stayed for five days. The house is very immaculate; not a trace of dirt or dust anywhere. Like last time, we were left with some yummy snacks and treats upon arrival. Kris & Daniel also went above and beyond when we wanted to go to the beach - they personally came right over and got some beach chairs, towels, and an umbrella from the basement for us. The house is very comfortable with high-tech smart devices and we were nice and cool despite the heat (and nice and warm when it got chilly later in our visit). Our last day, I accidentally pulled down a curtain rod when opening the drapes, and Kris & Daniel could not have been more gracious about it. Great house and great hosts! Thank you!

We had a wonderful stay. The house was clean, we had all we needed to make meals and the beds were comfortable. We would have appreciated blinds in the two smaller bedrooms but enjoyed the rooms nonetheless. My friends say Thank you for your hosting.

It was a great spot for a quick weekend get away. Claude was very responsive when I needed assistant before and during the stay.

Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

13/10 stars ✨. Run do not WALK on this property for booking. I don’t even know where to start! i’ll try to keep it short! This property and Host has been the best i’ve ever experienced, Everrr!. Let’s start at the bathroom the tub is huge and deep- the perfect relaxation at your finger tips.. Spacious Home and beautifully decorated.. and Clean.. When you enter the home the fresh clean smells takes you over.. from the personalized birthday note to snacks to checking in to making sure everything was to my liking .. Chef’s kiss ❣️ Diane’s place is a piece of Heaven snuggled in the city of Chi-Town! Ladiessss if you need the perfect home to feel like a princess on every level book nowww.. This property has the best combo for a man or woman ! i can go on and on but just make sure when y’all book - you leave some dates open because i’m coming back here EVERY time❣️😘