Condo vacation rentals in Chicago

I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.

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!

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.

The Airbnb was clean, exactly as described, and in a great location. Check in was easy and we were able to get settled right away. William was very proactive in communicating instructions well before our arrival. Overall, we had a lovely time visiting Chicago and would recommend staying here!

We loved our stay at this condo in the Wicker Park neighborhood of Chicago! The location was fantastic—just steps away from a great selection of restaurants, shops, and vintage/resale stores. The condo itself was beautiful, and the rooftop hot tub was a definite highlight. Highly recommend!

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.

From check-in to check-out, the stay was great! The place looked exactly like the photos and was in a great neighborhood. Shops, restaurants and bars all within 5-10 min walk. We even enjoyed the hot tub one late afternoon while enjoying the skyline and sunset in the back of us. Will definitely look to book this rental in our future Chicago trips.

Todd was great and very responsive. The Airbnb was nice and spacious for a large group and all the amenities kept up busy while we weren’t exploring the city. ~15 min uber into the city, location was great! Can’t hear any freeway noise from inside the apartment with windows/doors closed. Would definitely stay again with a large group

We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.

Beautiful home in Lincoln Square. The inside has clearly been extensively refurbished without losing the original Chicago charm of e.g. aged natural wood. At points it looks like an architectural magazine photo. Of particular interest to people who share a previous occupant’s love of sailing, but not tilted in that direction so much that you would need to be a fan to enjoy a stay. My family had a great time.

I had a wonderful stay at Andre’s! It’s a lovely and super spacious apartment in a great location, it had everything I needed for an extended stay. Myself and my two cats felt right at home. Andre was flexible with check in and check out, also very responsive and helpful for when I had questions. I would absolutely recommend this spot!

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!

The space was exactly as advertised, roof top patio was awesome. Location was great and Anna was easy to work with. Definitely recommend, we would stay here again.

Alex’s place is perfect for a short stay in a very walkable area of Chicago, with plenty of restaurants and bars to walk to near by! A cozy bed awaits you at the end of the day, and on-site parking is an added bonus!

Thomas was a wonderful host who truly went above and beyond. He gave us excellent recommendations for vegetarian restaurants, which we really appreciated. It was our first time visiting Chicago, and Thomas’s support throughout our trip made a big difference. The Airbnb was thoughtfully stocked with everything a guest might need—even umbrellas! Highly recommended.

I had a wonderful stay! The place was exactly as described—clean, cozy, and in a great location. The host was super friendly and responsive, which made the whole experience smooth and welcoming. I especially appreciated the thoughtful touches like I’d definitely stay here again and highly recommend it to others!

Great stay! The place was clean, comfortable, and in a convenient location. The host was friendly and helpful. I’d definitely stay here again!

Loved this spot! It was exactly where we wanted to be located - walkable to Aragon. the place felt clean, had high tech amenities, walkable to coffee and Eateries, convenient to train station. Lots of natural light, well decorated, cool stuff to look at and read. would stay here again.

This was our third time staying at Yvonne’s place. It’s spacious and in a peaceful location with street parking. Yvonne communicated effectively and was always responsive.