House holiday rentals in Near North Side, Chicago

Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!

They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!

It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!

Excellent place with lots to do. Local restaurants had delicious food, place was very clean and inviting. Will definitely be booking again in the future

Great getaway place to stay at. Beautiful patio area as well!

Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.

Wonderful home close to train station. Very convenient and cozy. Would recommend!

We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Great place. Great location. No issues at all. I would rent again. It's a good spot between the Gold Coast and Lincoln park and beer some really good restaurants. Place was as described and would have no issues staying there again.

We absolutely loved staying at Amy’s place! Easy check in/check out, great communication by the host, and plenty of room for 2 adults and 2 kids to stretch out. The mid century vibe was a nice bonus. Would 10/10 stay here again.

Our daughter was graduating from University of Chicago while our other daughter graduated from USAF flight school in Mississippi, and our family and friends visited from locations scattered around multiple time zones. Florin's location was simply the perfect place to handle such incoming chaos while lowering blood pressure to encourage a wonderful graduation experience headache-free. The rooftop experience was stunning, and everybody has been raving about the furnishings and easy-going environment in such a lovely place. The bathrooms and bedrooms were spa-worthy, and there were simply so many careful and thoughtful touches at this location that made it hard to leave! Florin has multiple parking options, but we only needed one nearby, offstreet parking place that was never a problem---surprising for a big city like Chicago! In short, this was probably the finest AirBnB we ever visited, and we are so grateful for such an exclamation point on a magical weekend. Thank you, Florin!

I had a fantastic stay at Sebastian’s place in Chicago! The house was spotless, stylish, and exactly as described. The location was perfect—close to restaurants, coffee shops, and public transportation, which made exploring the city super easy. Sebastian was a wonderful host: responsive, helpful, and made sure everything went smoothly. I especially appreciated the thoughtful touches throughout the home that made it feel cozy and welcoming. I would absolutely stay here again and highly recommend it to anyone visiting Chicago!

Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!

the house looked better than the pictures and the house was bigger than expected the heated floors were a great luxury I'd recommend to stay here but also recommend the owners 1 thing 1 the toilets need to be changed u have to wait like 5 mins in-between flushes they were very low pressured got irritating also the basement had a flood under the carpets near the pool table which made me not play pool bc I was standing in a soaked carpet which is an easy fix for future guest I'd recommend staying here if u want to be close to the city but not be in the heart of it and want to have easy parking n access to ur car

If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.

Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…

I stayed here for a weekend with my wife, toddler, parents, and sister. Everything was as advertised and very clean. Jamisyn is a great host and really goes the extra mile to make you at home, from handwritten notes to generous snacks.

Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!

Lovely space and a perfect location for exploring the city. Great restaurants within a short walk. Lincoln Park also just a short walk.

This is the perfect stay if you are looking for a place in Lincoln Park/Old Town area. Unbeatable location - walking distance to everything you could want. Plus, it is on a private street with lots of parking, even on a weekend in the summer. The apartment itself is so charming with plenty of space for a group of five. Very well stocked with everything you could need for a long weekend. Would absolutely stay here again!