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.

Tom was a fantastic host! Super responsive and helpful. His place was just amazing—gorgeous with so many amenities—hot tub, pool table, darts, etc. We had so much space to spread out and enjoy. The kitchen was extremely well-stocked-spices, condiments, cooking utensils. The location was great. We were a couple blocks from both the train and bus—so easy to pop on the bus to downtown-15 minute ride straight there. Parking was easy and excellent—a garage space as well as plenty of street parking with provided passes. Definitely recommend!!

a great location and nice neighborhood. The place itself is very spot on to the pictures it’s very nice and cozy. Overall just a good stay , host is responsive and great.

The apartment was neat and tidy. Parking was easy.

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.

James was a responsive host and the space looks just like the pictures, in a fantastic location in Chicago with easy walking to the L and all the great restaurants, bars, and shopping on Division and Milwaukee Ave. A few highlights: Our kids enjoyed the hot tub and though it is shared we didn’t see anyone else during our 1-wk stay. Plenty of space for the 6 of us with a nice open floor plan to hang out. The location was even better than I remembered, after living nearby about 10 years ago. James was very helpful and had clear instructions and typically responded in less than an hour. Some things to know: when we stayed there was a house next door getting gutted, and construction started at 6a on weekdays. Guests in the street-facing rooms may want white noise / earplugs esp if they are light sleepers. As other reviews state, the alley and garage space are tight. I’ve lived mostly in cities, but could not fit our minivan. There is some street parking a couple blocks away.

It was great place to stay.

Shivani and Riya’s place was a great spot for a weekend with friends to catch up and watch March Madness. There was plenty of space for our group of 6 and the place was exactly as described. The location also can’t be beat. There were tons of great restaurant and bar options within walking distance. I would definitely stay at this location again!

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.

We had a great stay! The pictures did not do the space justice, we loved it! And Charissa was so friendly and responsive, it really made our trip so easy

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.

This was an amazing stay!! Eugene was so so helpful and he responds so quickly. Great location, peaceful, safe. 10/10 would absolutely recommend.

I had a great stay at Newell’s place! The home was clean, cozy, and just as described in the listing. Check-in was smooth, and communication with Newell was quick and helpful the whole time. The neighborhood felt safe and peaceful, and I appreciated the extra touches like fresh towels, local recommendations, and a fully stocked kitchen. Whether you’re passing through or staying for a bit longer, this is definitely a spot I’d book again. Thanks for the hospitality, Newell!

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

This is our second stay here. the location can't be beat and we will continue to stay here when we are in chicago. I will note that it is VERY loud. Depending on who you have above you can make it even louder. the pipes for the heat are also extremely loud. This doesn't bother us so much as we go in expecting it. This is also not the fault of the host at all and this airbnb and host are both still great!

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

Best place to stay in Chicago with family and friends: centrally located in downtown Chicago, with public transport and bars & restaurants within walking distance.

This place was fantastic. Exactly what I thought it was going to be from the description and pictures. Kaye was super responsive and helpful when we needed info or to borrow something. She is a super host indeed. Will definitely be back!

This was our second stay at Susan’s. We love the location for visiting family in Logan Square. Convenient to bus on Diversey to go to Wrigley Field, and easy to park on Western to take Blue Line into Loop. Dining room table seats 6, kitchen is perfect for preparing brunch & dinner for all of us (6). Unit is very clean, garage is a great perk. Susan is very responsive and helpful. Will likely stay here again (if available) for future visits to Chicago.

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!