Apartment vacation rentals in Old Town, Chicago

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.

David's place was roomy and comfortable, clean and quiet!! The apartment is well within walking distance of several great restaurants and plenty of shopping. David himself was very nice, checking in with us even though his check-in instructions were clear enough. What a great host and neighborhood!! We will always check this listing first when coming to chicago from now on...and we visit at least every other month!! AND....the parking was FREE!!

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!

This was our second stay at the same property, though we stayed on the top floor last time, and it did make a difference in the noise. That said, it was exactly as described and had everything we needed for a comfortable stay during the winter, the parking off street was wonderful in the snow. It's close to everything we needed, some great restaurants, stores, and a bus stop. We will be back when we visit Chicago again!

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.

Host was great a communicating with us. The place was very clean and had everything we needed. Location was close to numerous restaurants and bars. The L was a 5 minute walk if you want to go downtown.

It's quite a beautiful and peaceful house. Kevin is really kind and patient. The location is so convenient that we don't need to spend much time on waiting Uber.

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

Elena worked hard to make it easy to get to her place, park and get inside. She was very attentive and responded quickly. Great place for 1-2 people.

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.

The place was very clean and close to our family, I will book again in the near future.

We stayed here for a staycation and it was delightful. Such a beautiful apartment and no need for a car! Everything is super walkable. Wonderful stay!

This was a great home base for a weekend of activities in the north suburbs! The kitchen had been recently updated and there were nice homey touches throughout - extra blankets, coffee maker, etc. I might have to return in the summer just for the adorable backyard space!

This was such an amazing stay! The location is perfect and within walking distance to everything. They offer free parking right on site. Everything was easy to find. The staff were super nice, and the host was quick to respond. The have plenty of toiletries as well. The gym was amazing. I was able to keep up my workouts during my vacation. I peeked in the pool, it was nice and clean. I will be staying here again.

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!

We absolutely enjoyed our stay! Everything was clean and mostly comfortable. However, when we arrived the heat wasn't turned on and it was 47 degrees in there in the middle of February. It also took over 2 hours for the temp to get to 65. Overall, a wonderful place but would have liked to warm upon our arrival.

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!!

You can’t go wrong with David’s place. Everything you need is there in a comfortable space. The train is so close. The beds and pillows and blankets are so comfy! The fireplace was nice because it was cold one day and we loved the washer and dryer because we ran the marathon. We loved everything about it!

Great location This airbnb a 10/10 I definitely recommend.Celebrated my daughter 3rd birthday here and I must say me plus the kids had a blast ! Bedrooms /Movie room/Game room/hot tub/massage chair all gave upscale

Megan’s place was exactly what we needed for our weekend trip. I was especially appreciative of the multiple sleeping options and loads of blankets!! The layout is compact but quite practical and functional. The remodeled bathrooms are spa like. Megan’s place is a wonderful place for a Chicago stay.