Monthly Rentals in Old Town, Chicago

We had such a great time in the heart of the old town in Chicago . Super cute beautiful house with all the comforts we needed, my son and I, for our 4 day stay. Comfy beds, all the amenities, great support staff and host. Top location with parking. Be there for the yearly art fair ! And any other time! Will come again!

Matthew is a great host , always present and willing to help, his place is cozy and very well maintained, great location and conveniently located near old town and downtown, close to the water and major shopping areas. Amazing short stay!

We had a wonderful stay at this Airbnb in Chicago! The space was incredibly clean, cozy, and felt just like home. The location was perfect—just a short walk to the zoo and only a 10–15 minute drive to downtown, which made getting around super easy. The neighborhood was safe and peaceful, perfect for relaxing after a day out in the city. The hosts were fantastic—very responsive and accommodating, always available to answer any questions we had. Would absolutely stay here again and highly recommend to anyone visiting Chicago!

The apartment was great - the building was lovely, especially the gym which was great to be able to use. Super close to multiple bus stops and an L line, which made getting around super easy. The apartment itself was clean and looked like the pictures! Only downside was I that I was not able to check in on time, however I was able to drop bags off, which was really helpful, and they were super responsive to any question or concern I had during my stay. Would definitely stay here again!