House holiday rentals in North Side

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!

Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

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!

Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

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!

Beautiful house very clean and comfortable. We'll be back very soon

We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!

Beautiful home in a quiet neighborhood with responsive and helpful hosts.

The stay was amazing. The only issue was finding parking especially at night was really tuff to find a stop.

Glomery was a great host. Our first trip to Chicago, so we weren’t too sure about the safety of the neighborhood, but overall a very nice experience and had all the necessities. Very clean and tidy. Beds were so comfortable with fluffy pillows. Plenty of towels, coffee and extra pillows. Easy access in and easy street pick up for Ubers. We had a nice time and felt comfortable.

Faith's place was great! The bed was super comfortable and her place was exceptionally clean! Quiet neighborhood. Easy access to highway, local restaurants and grocery store. The fresh eggs she gave us were a treat! She is an excellent communicator. Highly recommend staying at her place.

We had a wonderful stay. The house was clean, we had all we needed to make meals and the beds were comfortable. We would have appreciated blinds in the two smaller bedrooms but enjoyed the rooms nonetheless. My friends say Thank you for your hosting.

We had a wonderful stay at this Airbnb! The house was roomy, cozy, and super comfortable. Everything was clean and beautifully decorated, with a charming backyard and deck that made it feel extra special. The bedrooms were each uniquely themed and absolutely gorgeous, and the beds were incredibly comfy—everyone slept like a dream. The water pressure in the shower was perfect, and the hosts were kind and accommodating throughout our stay. Highly recommend this place if you’re looking for a relaxing and well-kept spot to unwind!

I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.

Great stay for a family trip! It was in a calm, quiet neighborhood where we felt safe that had all necessities! We did have a hard time with finding available parking on the street a few nights out of our visit, but other than that it was great and comfortable! We have already discussed visiting again and staying at Sarah’s!

First time staying at an Air Bnb and it was amazing. Instructions were very clear and the place had everything we needed!

We had a truly wonderful stay at Casa22. The home is beautiful, luxurious, and impeccably maintained — everything was clean, spotless and thoughtfully arranged. It had all the essentials we needed for a comfortable extended stay with our family, including a well-equipped kitchen, and spacious layout. The hosts, Narcis and Gabriel, were fantastic — extremely responsive, clear in their communication. They provided detailed instructions that made check-in, check-out, and everything in between seamless. The neighborhood is quiet, safe, and very family-friendly, with easy access to main roads — a great location if you're planning to explore Chicago without the stress of city parking. Having a car made it easy to get around, and the area itself felt peaceful and well-kept. If you're visiting the Chicago area and looking for a clean, elegant, and well-managed place to stay, I highly recommend Casa22. We would absolutely love to return!

Amazing value! Three bedrooms - two decks - great kitchen. This was a great central location for my father/brother visiting. I live in Logan and there are no good hotels nearby and this was even better than a hotel! Parking can be a bit stressful as you are right on Diversey but it was less stressful than I thought it would be. Would book again!!!

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 stay for a 3-night family getaway. Appreciated the bunk-bed room for kids. (With toys!) The game room in the basement was a hit, but watch your head if you are tall. Overall great value for a large group (we had 10), especially with kids, but the construction on I-90 (obviously not the fault of the owner) makes getting to and from downtown a major chore.

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!

This was one of best AirBnbs that I have stayed at this year. Clean, great host, lovely house. Comfortable beds, clean bathroom, big shower, a sauna! Highly recommended.