Apartment vacation rentals in Old Town, Chicago

Absolutely 5/5 everything looks exactly like the photos! The space is big, spotless, and feels incredibly cozy. The location is perfect…!!surrounded by everything you need, including Target, Whole Foods, Starbucks, Sephora, and a variety of restaurants and shops.

We had a great stay. The place was clean and cozy. The three of us were able to explore the city and then return to relax in the garden unit. Many great places to eat in walking distance. The free and plentiful street parking was a bonus. Thanks for hosting us.

David's place is a gem located on a quiet block in one of Chicago's best neighborhoods--walkable to everything we wanted to do as well as the Brown Line. The pictures don't do justice to the size of the place. It was plenty roomy for our two families to spread out. The fragrance-sensitive people in our party appreciated that everything was clean but without the overperfumed linens and interiors they often encounter. David was a great communicator and the whole process was seamless. Would stay again!

Tiffany’s place is so comfortable and charming. Beautifully decorated, with comfortable furniture/beds and a fantastically appointed kitchen, you won’t regret booking this spotlessly clean gem. As a coffee snob, the electric kettle and French press were a dream come true. The plants everywhere make it feel warm and inviting and the turntable was a delightful surprise that we really enjoyed. We could not have been more pleased with this beautiful and cosy home.

Nice place to stay for the weekend with my friends. The place was clean and large. You get everything you need. Plus, it is walkable for a quick lunch or convenient store. We drove with a suburban (super large SUV). So it was challenged to park because of the one-way street with cars parked on both sides of the street. Also, the bedroom in front of the bathroom was a little bit cold at night. Overall, great experience and stay at Afsha’s home.

This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

This is a very clean and comfortable unit. The beds are very comfy, the comforts are wonderfully soft. Basic toiletries and kitchen essentials are provided. The location is excellent for us, as we have young grandchildren and a dog, both enjoyed wicker park. Many restaurants are close enough for walking.

Needed a place close to a friend that I was visiting in Logan square. This was perfect, 5-6 blocks away. Quiet. Clean. Felt safe.

We really enjoyed our stay. Song was responsive and helpful. The property was as advertised. It was very comfortable, clean and quiet. There is easy access to public transportation and downtown is also within walking distance. Check in and checkout were very simple/easy. We would stay here again and can recommend the property for families looking for a place to stay in Chicago.

Cozy small rooms to rent. Would just suggest a filtered water pitcher and a microwave for ease of use. Otherwise bed was comfortable and felt at home.

Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.

Shaun and Christina were extremely polite and helpful! They were very attentive but not overbearing and genuinely cared about our experience. The house was awesome, very spacious and clean with a full kitchen and even laundry machines on site. The parking space was also very convenient and appreciated! Would definitely stay again!

Scott and Mindy made our stay perfect, despite issues we had with airlines they went above and beyond to make us feel welcome! I would stay with them again in a heartbeat.

We are happy with our stay at Liz’s airBNB. Liz was responsive and very accomodating to our specific check-in requests. Her place was spacious and easy to check-in. It had everything we needed. We were very grateful to easily find 2 street parking spots outside of her place. Her place was perfect for us as we were visiting Chicago but wanted some amentities that are not traditionally available in the city itself- i.e. parking spots, and easy in/out capability. I would recommend this airBNB and we would definitely stay with Liz again.

Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

The garden level unit was very comfortable and we felt right at home. It was well stocked with towels, clean linens, soaps, coffee, tea. We had strong WIFi. Great kitchen and well stocked with dishes. We will definitely stay here again when we return to Chicago. Thank you Eric.

Great stay! The view & the convenience of being downtown along with the parking was nothing short of exceeding my expectations. Would stay here again!

I absolutely loved and enjoyed our stay. Stephanie responded so quickly and was willing to accommodate an extra key during our stay. The apartment had a beautiful view and there were so many clean towels, extra linens and the amenities were awesome. The pool was warm and the gym had many separate areas to workout. The 29th floor is a wonderful place to work virtually and make your coworkers jealous. We explored the wine room and spent some time in the sauna, both of which were nice. Target being next door was so convenient and we parked 5 minutes up the road with SpotHero — don’t risk parking at Target. The ONLY difficulty would be accessing the keys and learning which floor the amenities were on. We spent a few minutes trying to get the keys out of the lockbox since it was jammed. Our second set of keys did not allow access into the pool. Aside from that SMALL hiccup, I would absolutely visit again and would recommend this place to anyone looking to relax and explore the city.

I had surgery at the hospital around the corner and stayed here for few days as I couldn’t climb the steps to my apartment post surgery, highly recommend. There are two steps down into the apartment that I was easily able to handle, the shower in the back of the house has grab bars, and overall the house was very accessible and easy to navigate with my walker. Would stay again!

Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

What a great stay! The boat was even better. He was immediately responsive and accommodated extra when caught in a pinch. He was very communicative and helpful. The place was very comfortable for both us and the dogs. It felt like home! Would recommend to anyone.

The apartment is new and very well designed. It's stocked with everything we needed for a week stay for a family of 5. Great location just steps from the subway, grocery store, restaurants and bars and walkable to many tourist destinations. A big plus for me is the on site gym, with everything I needed for my workouts. The only drawback is the time it takes to set up the virtual key. With mostly adults in our group, every single one had to go through a screening process outside airbnb and download an app, which we didn't mind given that we had plenty of time ahead of our stay but I can see that it could be an inconvenience for next day bookings or, for example my elderly parents that don't have hi-tech phones and would not be able to access this property with their own phones.

Mariam did a fantastic job of being responsive to everything we needed. My brothers bachelor party was a success because of this house. We would stay here again.