Holiday rentals in Chicago Loop

Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!

Mark was a great host. He went above and beyond! Made sure our stay was great the whole time we were there! Very responsive and accommodating! Definitely a great stay! Will be saving for future stays!

We have traveled to Chicago with a party of 5 - 3 adults and 2 kids in February 2025. We stayed for 3 nights and really liked Mark's place. It is really bigger than it shows on the pictures, so it really accomodates 6-8 people easily. Host was responsive and provided helpful and timely instructions. Would stay again.

Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.

Wonderful stay as always, thank you so much!

Everything was great! Thank you so much for everything!

Daniel's place was perfect for my friends and I who were in town for a wedding. The house slept 6 of us comfortably and there was plenty of space to hang out together. Everything was clean and there were plenty of towels and extra linens on hand. The house is in a nice area. Except for a Starbucks, it's about a 10 minute walk to most of the cafes, shops, and restaurants in the area. Though there's a cute little sandwich shop just down the street called Rosie's that my friends and I loved! Daniel and Carrie were responsive and everything went smoothly. Thanks for a great stay!

This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.