Apartment holiday rentals in Old Town, Chicago

We had an excellent stay. Host was responsive. The hair dryer stopped working and the host dropped off a new one right away. Would recommend.

We loved staying here. The apartment is very stylish, comfortable and quiet. Its also in a great neighborhood and the parking arrangement worked out great. We look forward to staying here again in the future. Thanks for a great time!

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.

We had a great stay here - we were just a few houses from a Main Street with shops and several restaurants. A 10-15 minute walk in the other direction led us to more places. David was proactive communicating with us prior and during our stay. As stated in the listing, parking can be challenging but we managed to find parking all but one time. David had told us an app to use for parking spots and the one time we needed to use it, we had a spot for a few dollars until noon the next day. The unit size was great for our party of 5 and the home is in a quiet, safe neighborhood. We would definitely stay here again - it was less than 20 min to downtown, close to the train, close to Wrigley. Highly recommend!

This was our first time staying in an Airbnb and questions were answered quickly and kindly. We found the apartment clean, cozy, comfortable, close to many amenities, including train, and walking distance to our daughter’s apartment was convenient. We didn’t use the kitchen, except for the Keurig coffee maker and filtered water pitcher, which were nice and it was well stocked. The bed was comfortable and shower nice. Judith was a gracious host, kindly responded to text messages, and available. Thank you so much a great stay in Chicago!

I took a weekend just to get away from my normal surroundings. Dan's place was perfect. It was clean, peaceful, and well equipped. Dan was an awesome host. He checked in on me and I really appreciated that considering I traveled alone. I felt secure and like I had a friend nearby. I recommend this place. I would definitely stay again!

I had an amazing stay at this Airbnb! The location was perfect—everything in Chicago was about 20 minutes away, making it super convenient to explore. Chicago was freezing this weekend, but the host had the heater on before our arrival, and each room had an additional heater and fan available, which was such a thoughtful touch. The space itself was incredibly spacious, so everyone had plenty of room without feeling on top of each other. The bed linens were top-tier—honestly, they felt like five-star hotel quality. And the cleanliness? Spotless! Everything was meticulously maintained and aesthetically pleasing, making the apartment feel warm, inviting, and well put together. Another huge plus was the parking—it made our stay even smoother. On top of that, the host was super flexible. Our flight was in the late afternoon, and while she didn’t initially offer late checkout as an option, she was kind enough to accommodate us for an additional fee, which we really appreciated. Impressed!

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.

Had a great stay at Zarko’s place. Located in a quaint, quiet neighborhood, he offered a comfortable and clean apartment room with a separate entrance to the house. Onsite parking was very helpful. During our short trip we didn’t meet Zarko, but he was attentive via calls and texts and gave clear instructions for parking and check in. Would definitely recommend a stay at Zarko’s!

Great space and location, short 5 min walk to the train station. Song was an excellent host and the space was modern, clean, and comfortable.

Great place and neighborhood. The place was definitely cozy and matched exactly what the listing described.

Elena’s cozy basement suite was very clean and reasonably priced for being so close to both Chicago and Evanston. Private parking was an added gift. The bed was comfortable and all of the linens smelled fresh.

Great home in a great area! We loved the house it was just what we needed for our trip to Chicago.

Nice place, right around the corner from the Constellation music venue -- that is why I came here. The place was vey convenient and nice. Parking was pretty easy.

A Great experience every time! If your going to Chicago this is the place to stay!

This cute apartment is right on Roscoe Street in the heart of Roscoe Village. Everything nearby is very walkable, and a train stop is just a few blocks away.

Just me and my friend stayed for 2 night and it is definitely bigger to host more. But we loved the view and the cleanliness. Host was very responsive and everything went smoothly.

Had a great stay at such a great location. Coffee and food all within a few blocks walk, plus a target on the corner incase you forgot anything like we did 😅. Stephanie was helpful and responsive and sets up place for easy check in and out. 100% would look to stay here again!

Very responsive homeowners, the rooms were left with plenty of accommodations such as towels, pots and pans, a Keurig, etc. The place was left to us very clean and ready for our group upon arrival.

Had a fantastic stay! The location was perfect—so convenient to everything we wanted to do. The space itself was spotless and well-maintained, making us feel right at home. We especially loved the amenities, which were thoughtful and really added to our comfort. The deck was absolutely beautiful—has potential for the summer. Highly recommend this place to anyone looking for a great stay !

One of the most understanding and responsive hosts I have had the please of dealing with. Beautiful space, safe area, walking distance to store and bank. Parking available in structure but at a cost. 10/10 recommend.

Nassa was a warm, responsive, and wonderful host. We had an incredible time, had everything we could possibly need and when there was a TV issue, Nassa ventured out in the cold to help us. Great place!!!!

From start to finish, our stay at Megan’s place was wonderful! The apartment was exactly as described clean, comfortable, and in a decent location. Megan was incredibly helpful, offering fantastic advice on things to do and where to eat in Chicago. She responded to our questions quickly, almost like our personal tour guide, and went above and beyond to ensure we had everything we needed. We’d highly recommend staying here.