Apartment vacation rentals in Old Town, Chicago

Nice and clean 1 bed unit for a week of comfortable stay. Thank you for hosting us!!

Were I in the Chicago area I wouldn’t hesitate to stay there again.

A great neighborhood spot! A cozy classic Chicago apartment with gorgeous midcentury accents. Extremely walkable and easy to access the Montrose brown line. The kids loved the trundle beds in the back sunroom. They have very smartly added blackout shades to the room to really create a child friendly sleeping space- a real gift! Loved the whole place, would love to stay there 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.

Definitely a great weekend! The look, and feel of the place was very comforting, and had a great flow. Design was tasteful, and anything that was needed was right where you’d expect it to be! A definite recommend!

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.

it was my first Airbnb experience and it was very pleasant. The location is perfect to get to the place, but perfectly peaceful in the night.

A great place to stay for a family to explore downtown Chicago. The location is convenient, with easy access to major attractions, and restaurants. The home was clean, cozy, and well-equipped — we truly felt like we were at our own home. The host was responsive and thoughtful, which made our stay even more comfortable. Highly recommended!

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!

We needed a place to stay in the Roscoe Village area, and this was perfect from a location and size standpoint. It is urban-on a well traveled street, close to the metro stop, lots of coffee shops and places to eat. Appreciated the white noise machine in the bedroom and the bathroom towels were very nice. Communication was excellent and easy to understand. Highly recommend!

Nice place to stay in a good neighborhood! Would stay here again, thank you!

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

This was our second stay here. Eric’s place was very clean and comfortable. It was very well stocked with everything we needed. Our stay was great!

This place was incredible. My kids and I loved staying here. My young daughter had asked to stay in a "fancy hotel" on our trip, and this blew her mind with the views over the city, how nice the space was, and the pool and hot tub that we pretty much had to ourselves every evening. The kitchen had the things we needed to make our own meals. And we were within easy reach of every place we wanted to go. The included parking spot really took things over the top to make this a great deal and an amazing stay for our family.

STAY HERE - no regrets. The apt building was easy to find with a pull thru drive to unload luggage and a lobby for my family to wait in while I parked. Parking was affordable and close by using the app as suggested, many within a 10-minute walk. Getting the key was easy and the apartment was clean and tidy, exactly as described. The city view was stunning, you can see Lake Michigan and on a very gusty morning we could see the massive wave whitecaps from the window. Plenty of household items available from plates and cups to linens and soap. The building was well maintained, safe and the residents friendly. The amenities (pool, gym, bball court, *jacuzzi was not open yet) and the rooftop lounge and views were all great! Stephanie was attentive and touched base a few times to check in, but we didn't need anything! Location is walkable to much of the city-the Willis tower, Millenium Park and the Shedd Aquarium/Field Museum. Train is close too! Target is literally next door- so handy!

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.

Avantika’s penthouse apartment was absolutely lovely. The space was comfortable and well-designed, with beautiful bedrooms and impeccably clean bathrooms. The kitchen was modern, spacious, and had everything we needed. Avantika was incredibly kind, helpful, and very responsive throughout our stay. We had a fantastic experience and will definitely be back!

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.