Condo vacation rentals in North Side

The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!

A Designer’s Dream – Absolute Perfection! This home is truly exceptional—every detail reflects thoughtful design and top-tier quality. It’s a designer’s dream, with stunning décor, a comfortable and beautifully clean space, and every amenity you could possibly need. The furnishings and finishes are stylish and well appointed, making the entire experience feel luxurious and relaxing. But the real showstopper? The backyard! It’s like a second living room—lush, tranquil, and designed for ultimate comfort and enjoyment. We loved spending time out there and honestly didn’t want to leave. It's so much better than anything a hotel could even begin to provide! We will absolutely be back!

The renovated classic Chicago greystone is spectacular. This is an amazing update of an architectural gem. The space has all modern amenities but the character and charm are thoroughly maintained. The spaces are spotless. Rogers Park is a wonderful lakeside neighborhood and is a melting pot of ethnicities and cultures. There are great restaurants within walking distance as well as close by in Evanston, Andersonville, etc. The Metra and the El are an easy walk. Lillian was so accommodating and proactive. We loved this stay and will be back.

I stayed for a few nights at Sean's place and it was lovely! The apartment was really nice and very spacious, and the location was perfect. Sean was flexible with my schedule changes and made sure I had everything I needed. Oh, and the bed was SO comfortable!

everything was extremely nice, unfortunately the knob to change from shower to faucet was detached so we could not utilize the very large beautiful bathtub. The front porch light also needs to be replaced, we opted to leave the front door open to be able to see outside after dark. Other than that everything was extremely nice. Still worthy of a five-star review.

Very nice place. Looked professionally cleaned. Matt was prompt with his replies and managed to accomodate a late check out, which was helpful. 10 mins walk to Logan Square station where you can catch blue line to downtown.

I had an amazing stay! Place was very accurate to the post on Airbnb and the host was very polite with clear instructions, and check in! Thank you for providing such an amazing Chicago experience for me and my husband!

Ken’s place was a great stay! Such a unique home with so much to see inside—decor, art, photos, and trinkets. We enjoyed relaxing in the space between exploring the city. Would recommend to anyone who is considering staying in Chicago!

We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.

Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!

Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.

A really cute, cozy apartment in a great location. Brock was wonderful and very responsive. There was always parking, and it was close to everything. Children upstairs were a bit noisy during the day but overall, my stay was enjoyable and I would definitely recommend the place.

Great host and great stay! Beautiful home. Thank you so much!

Very close to public transit, grocery stores, and restaurants. Quiet neighborhood and comfortable sleeping.

I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!

Cindy was a lovely and responsive host and the apartment was great. She was very responsive and let me adjust the booking without any hassle. There was plenty of towels and blankets, and the coffee area was well stocked. Location was in a great area of lincoln park very close to the zoo & actual park area and not a far walk to the cta/many bus stops. Would definitely recommend!

I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.

Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.

Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!

Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.