Condo holiday rentals in North Side

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.

Allen's place is great, I stayed for five days and loved it! My highest compliment is that it's super well-equipped, to the point it feels lived-in (in a good way). For example, the kitchen is stocked better than mine, you'll find it easy to make a meal here. The rest of the unit is well thought out, too. My one piece of advice is to pay reallyyy close attention to the check-in instructions. There are multiple entrances to the complex, and they look similar. You might end up trying the wrong lockbox 10 times if you're not careful :) Overall, I highly recommend this place! Friendly neighbors as well!

Chip and Lito's place is a dream! Spacious, clean, quiet, and convenient to restaurants, the "L", and the beach. Apartment is very well appointed, yet not cluttered. The shower is awesome! It was very nice to have a full kitchen, with coffee makers and dishwasher. I definitely plan to stay here the next time I visit Chicago!

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.

This apartment was a real gem. The back patio was so lovely to hang out on during the cooler evenings. I loved how accessible the building was to so much of Chicago, both via the blue line and the bus that stops right outside. Would definitely come back!

Loved our stay here! Perfectly located in a gorgeous neighborhood. Great coffee and restaurants within a few minutes walk!

Beautiful condo. A little steep in price but excellent location and ample space. There were some small issues with fruit flies collecting near the back door but they were responsive and it was quickly addressed.

We had a great stay in Logan Square. The location has walkable access to the Blue Line making downtown easy. While this is a lower level unit, this does not feel at all like your standard “garden level”. It was full of windows and bright. Furniture was very comfortable. Bathrooms well appointed with amazing shower pressure. The bedroom is so quiet you get a great nights sleep. Bonus points for lamps on BOTH sides of the bed. The closet had high quality hangers plus good storage. The kitchen has everything needed for cooking or for storing leftovers from fabulous restaurants in area. The garage is a great bonus. Our young adult children live in the area and it was prefect for them to come over, hang out and visit with us. We spent time outside in the garden area with the fire table. Bryan was very responsive and helpful through our four-night stay. We will be back!

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.

Feven was very responsive to all our questions in real time. The place was perfect for four adults and two kids! The place was walkable to a few restaurants and coffee shops and easily drivable to other neighborhoods. We did happen to be in the neighborhood for the PR festival, which we didn’t realize. It made traffic a little tricky but otherwise we didn’t hear too much noise from the festivities. We found a nearby coffee shop and playground which we frequented daily and met lots of friendly neighbors on our walks.

Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

Awesome location, near lots of local restaurants, public transit and a major grocery store. China Town is a short bus ride away. The neighborhood itself is awesome, helpful neighbors and very friendly local vendors. The apartment itself is clean, inviting and has everything you could possibly need. Cory and Alexis were very inviting host, quick to respond to my questions and were very informative. I will be keeping this location in mind for my future Chicago travels.

Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.

We love the place which is spacious, quiet and surrounded by the friendly neighborhood. Aldi, Target, Whole Foods are walkable distance. The layout of the house is easy for the guests from different families. Kitchen, living room, family room are popular for the gatherings. Kate is very responsible and helpful with any questions.

My family and I loved our stay; the apartment was adorable and had everything we needed. But the location is truly the highlight! Walking distance to North Ave beach, Lincoln Park Zoo, all the fun restaurants and shops in Old Town, and the famous Second City Comedy Club.

Such an awesome place to stay, very safe neighborhood. Mark was very responsive in the chat and asked us if we needed anything else right after we checked in. The best part was that their is a dedicated parking space which is very convenient and easy access to the place. For sure will be checking in next time when going to Chicago.

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.

gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.

Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

You can walk to Northwestern University, and the surrounding environment is clean, comfortable, and pleasant.The house is fully equipped, and I love cooking in the kitchen.Our whole family had a wonderful week here.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.