Apartment holiday rentals in North Side

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!

Jim was a great host and so accommodating. It was great being right downtown and just a two block walk to the lake. :-) There's a lot of places to grab coffee, baked goods, and resturants for dinner within walking distance. My stay was perfect for me and what I needed in my room with lots of charm. Thank you Jim!

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 had everything we needed as well as more! The neighborhood is walkable with great bars and restaurants and the nearby train station made it easy to travel around the city. We will definitely consider David’s place again for future visits to Chicago!

This was our first time staying in an Airbnb and questions were answered quickly and kindly. We found the apartment clean, cozy, comfortable, close to many amenities, including train, and walking distance to our daughter’s apartment was convenient. We didn’t use the kitchen, except for the Keurig coffee maker and filtered water pitcher, which were nice and it was well stocked. The bed was comfortable and shower nice. Judith was a gracious host, kindly responded to text messages, and available. Thank you so much a great stay in Chicago!

I had an amazing stay at this Airbnb! The location was perfect—everything in Chicago was about 20 minutes away, making it super convenient to explore. Chicago was freezing this weekend, but the host had the heater on before our arrival, and each room had an additional heater and fan available, which was such a thoughtful touch. The space itself was incredibly spacious, so everyone had plenty of room without feeling on top of each other. The bed linens were top-tier—honestly, they felt like five-star hotel quality. And the cleanliness? Spotless! Everything was meticulously maintained and aesthetically pleasing, making the apartment feel warm, inviting, and well put together. Another huge plus was the parking—it made our stay even smoother. On top of that, the host was super flexible. Our flight was in the late afternoon, and while she didn’t initially offer late checkout as an option, she was kind enough to accommodate us for an additional fee, which we really appreciated. Impressed!

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.

A comfortable and convenient place to stay while visiting family in Chicago. Appreciate the dedicated parking space, lots of towels, laundry in unit, and well stocked coffee bar. Thank you for the thoughtful hospitality!

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!

A great airnb plenty of space and great location 5 minutes from state street and more I can’t wait to come back in the summer !

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

Elena’s cozy basement suite was very clean and reasonably priced for being so close to both Chicago and Evanston. Private parking was an added gift. The bed was comfortable and all of the linens smelled fresh.

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.

It was perfect for what we needed. The hosts were excellent communicators.

This cute apartment is right on Roscoe Street in the heart of Roscoe Village. Everything nearby is very walkable, and a train stop is just a few blocks away.

Great location. The views were amazing. The penthouse is very clean and modern. Everything you need is available. Even Qtips! Staff on site onsite is very helpful and nice.Would love to stay 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.

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!

Extremely well thought out layout. Very comfortable and inclusive amenities throughout. Game room...BOSS! Theater room... EPIC! Bedrooms were very charming and modernly decorated. Massage chair... soo relaxing! Entire home was very clean and inviting! Nassa is a FABULOUS host! He even graciously allowed me a complimentary EARLY check-in! Thank you Nassa!

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.