Condo vacation rentals in Chicago

William has a fabulous place that was perfect for what we needed. Clean, plenty of linen and towels for when we needed it, and every supply we could ask for. Yes, the train was next door, but surprisingly didn't interrupt anything for us, so I'd say that description was accurate. We would absolutely stay here again.

This place was great from the balcony to the fenced in area behind the house. Parking was easy and free on the side streets. The retro appliances really stood out in the kitchen. Wonderful are for dogs to go out easily and safe to be able to walk them. A few parks nearby. Great place to stay with lots to do within walking distance.

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.

I hosted my sisters bachelorette of 15 girls at Tom’s place and everyone loved it! The 3 bunk rooms worked out super well and the master was incredible spacious! The main floor and downstairs had comfortable seating for all of us and everyone especially loved the patio! Tom was also accommodating to a slightly early check in and was responsive with questions. He also shared a parking garage spot as well as 2 days of permit parking, which was super helpful! My only note is that the bnb definitely showed signs of previous groups. There were leftover crumbs/ food pieces in the kitchen and downstairs on the floor and in and around the cabinets/trash. The hot tub had a funky smell to it and obvious gunk on the inside (Tom was able to help us find the shock and fix the smell). Overall it’s a great location and spacious home for several people!

Absolutely loved Cynthia and Thomas's place! They were proactive in their communication and responded promptly. The space itself was beautiful and very clean upon arrival. I loved the small balcony area and the bathroom! The bathroom itself was worth the price for an amazing shower and spa experience. The house was so peaceful and quiet, but it was also located near so many things to do. Definitely looking forward to staying again in the future!

The apartment was neat and tidy. Parking was easy.

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.

Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

Great place for our Chicago spring break trip. House photos were current, it had listed amenities, and was 2 blocks walk to the Blue line and plenty of shops/restaurants were walking distance. Nice neighborhood close to the action. I would note a few things for people considering this house : 1) Parking was readily available near the unit during daytime hours, but was trickier in the evenings/weekends. We did (eventually) always find a spot somewhere nearby when we drove places. 2) Layout of bedrooms is: main floor king bedroom with private shower bathroom; main floor queen, main floor full bath. Basement has other king, two queen rooms, and other full bathroom. 3) The quiet hours in the rules make even more sense when you realize this unit is 1st/basement and someone else (with little kid(s) lives on 2/3. It worked well for us since we had kids with us too so our noisy times were mostly in sync. 4) Ally was super responsive when we had questions or issues. A+ for that!

Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.

This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

Great stay! The apartment is very large with two full bathrooms, which is nice for family stays. No formal kitchen, which is fine - we didn't need one.

We really enjoyed our three nights in Matt's roomy upstairs apartment. Great to have a space in his garage; the car stayed parked there while we took the blue line downtown each day. It was an easy 10 minute walk to the Logan Square station. If you're flying into or out of O'Hare, it would be convenient, since the airport is the last stop on the blue line.

Eugene is an amazing host that is very communicative and flexible. This property looked just like the pictures, clean, safe and bigger than expected. The property is in walking distance of two amazing restaurants Taqueria Varitas and a breakfast place called peaches. 10/10 highly recommend!

such a great lovely place to stay thank you for the great hospitality!

Wonderful, everything was clean and lots of fun stuff nearby I recommend anyone book here it’s a great stay

Beautiful spot, cannot be be beat, was a block away from our favorite pizza spot and a few blocks from our dumpling place. The rooftop view is stunning, panoramic view of the city. As for the apt — it was very well laid out, maximizing all of the space and the softest couch we’ve had in any Airbnb to date. Hosts were in constant communication and we were only there for a long weekend university visit. Very happy with the place, would use again this summer or for any future visits to the city.

I always have the best time in Chicago, but Kaye’s place made this trip even better! I loved staying here so much, I actually extended my stay by a few days. Kaye has thought of everything, and to quote Tina Turner, she is “simply the best!” This is my favorite Airbnb I have ever stayed in and Kaye is the best host! I would recommend her place to all my friends and family. Can’t wait to visit again!

Susan's place was a great affordable option for a cozy place that isn't too far from downtown! the local places around the unit were also super nice! The space was fairly cleaned and well organized. There's plenty of amenities that made the stay more comfortable.

Convenient location with lots of space

Great stay!! Perfect location and it suited our family and dogs wonderfully while we weee in Chicago for 4 nights. I passed this listing along to a friend who is looking to stay in the same area. Overall great experience and we loved our time there!

Seth’s place worked out PERFECT for our group. Some of the city’s best restaurants are right there. The place itself is just gorgeous, the beds are comfy, parking is super easy and Seth was super responsive. Would definitely stay here again!