Holiday rentals with a fireplace in North Side

This place surpassed my expectations. Felt at home. Great environment, lots of room for me and my 3 kids. My husband loved it too

We were in town for a bachelorette weekend and Austin’s place was perfect. It was clean and comfortable. Having outdoor space was important and we were pleasantly surprised that there was a rooftop space in addition to the yard. Austin was also super responsive even when we had to reach out late on a Friday. A couple notes that are just FYI. Austin’s place is across from a school which wasn’t a problem at all except we arrived around 3:00… right at pick up time. The road was closed just for a short bit, so you might want to check in later of you’re checking in on a school day , or plan to park around the block. And there is no longer a bunk bed with a full size bed on the bottom. We would book this place again in a heartbeat and really enjoyed our time and the location. Thanks Austin!

We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

Nicole and Matt’s place is a well-located, spacious apartment perfect for a family of four adults. Situated near Lincoln Park, it’s within walking distance to the park and a fantastic selection of restaurants. Nicole and Matt were also kind enough to provide recommendations and we did enjoy a couple of them. The apartment is clean, well-maintained, and fully equipped for a comfortable 4-day stay. The hosts were very responsive and provided clear check-in instructions. One consideration: the unit is spread over three levels, with the master bedroom on the top floor—potentially challenging for those with mobility issues. The second bedroom, located on the ground floor, lacks natural light and feels a bit confined. Overall, we had a pleasant and convenient stay.

Lizbeth’s place was a great stay! It was cozy, clean, and had more than enough space for me and my three friends. While it was a little farther from the city center than I initially expected, the neighborhood made up for it with tons of great restaurants nearby—there was always something good to eat just around the corner. Lizbeth was also a fantastic host—very friendly and super responsive whenever we had questions. Would definitely recommend her place to anyone visiting the area!

Great stay! Loved the decor and amenities. Everything was just as described and my family really enjoyed our time there. Would stay again!

Had a great stay and Damien was extremely responsive with our requests. Would definitely recommend!

We were in town for our daughter’s graduation from Loyola and had our other 3 adult children in tow. All 6 of us stayed, and it was a bright, comfortable place to hang out, cook meals and enjoy time together. Very quiet at night. Perfect for us!

Lin communicated clearly and was helpful throughout the whole process. The space was perfect for our needs, close to the event we were there for and in a lovely neighborhood near a small park close to a variety of great family restaurants. Happy to go back should the need arise.

Great place overall!! The neighborhood was very peaceful and clean. My favorite thing about this place was the parking! I did not have to worry about parking at the front. Since this was pet friendly we did decided to leave two clean pet bowls for the next family to use for their pets. I would definitely book my next stay here again!

Song’s place was perfect for our family trip to Chicago!

Me And my fiancée had a great time, clean place, and worth every cent, only downside is parking.

McKinley Park is a safe beautiful neighborhood near the Orange Line. Joyce’s place is spacious, clean and well-appointed.

Great location and wonderful hosts! We will definitely be staying here next time we come to Chicago.

Antoinette was very accommodating and kind! The stay was very comfortable and homey.all instructions were clear and check-in/check-out was a breeze! We walked over to the bakery ahead suggested in the morning too and it was delicious.

Tommy's place was in a great neighborhood in Chicago. Very walkable. Close to both the Red and Brown subway lines. Wrigley Field is less than a 10 minute walk. After staying at multiple Airbnb's over the years, this place was in the top 3 for cleanliness. I was also surprised by how comfortable the bed and pillows were. It's on the second floor of a 3 unit building and didn't once hear anyone above or below us. The back garden would be a great place to hang and read or just enjoy a beer or glass of wine. Though he left snacks, wine and beer for us to enjoy, we didn't have time as we were out enjoying all that the city has to offer. I would stay here again if visiting Chicago. This guy knows to host. Thanks again Tommy!

We had an amazing 5-star stay in Chicago! The home was spotless, artfully decorated, and full of thoughtful touches like a piano, guitar, and a welcome gift. We loved the 360° rooftop deck with a fireplace and the fully equipped kitchen with a balcony. Beds were super comfy with high-quality, clean bedding. Though close to downtown, the home is on a quiet street and offers keyless entry — very convenient. We also appreciated the private garage with EV charger, 3 TVs, 2 fireplaces, and a great Nespresso machine. The location is unbeatable—near top spots like Swift & Sons and City Winery. Natasha was an excellent, responsive host. We’re already planning to return!

We had an excellent time here. Our whole dance team was able to stay comfortably and safely. We managed to fit 5 cars in the parking which was essential to us. It was all clean close to everything we came to Chicago for. The communication with the host was great and always prompt. We loved it here.