Apartment holiday rentals in Downtown Chicago

My stay was nothing short of exceptional. From the moment I arrived, I was impressed by the impeccable attention to detail and the luxurious touches throughout the property. Every corner exuded elegance and comfort, from the high-end linens and designer furnishings to the spa-like bathroom amenities. Mesh went above and beyond, offering a level of service and hospitality that truly rivaled any five-star hotel. The location was prestigious, private, and convenient, making it the perfect retreat. This place is a sophisticated and unforgettable experience, it’s simply unparalleled. I cannot wait to return!

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.

Our stay at Charissa's condo was perfect for our short but full stay in Chicago. We enjoyed the walk to the L Train and the neighborhood around it, and the space itself was accommodating and even luxurious when it came to the bathrooms. The instructions were not complicated for accessing the condo, the space was well kept, and we had no trouble seeing it as a main staple of our amazing weekend.

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!

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!

Very quick to respond to questions and great detailed instructions. The place was clean and comfortable! Awesome!

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!

My husband and I stayed here over the holidays. The apartment was pretty well appointed, clean and is in a good location- centrally located for our purposes of being near family and close enough to the expressway to get to the city.

This condo is well appointed and stocked with coffee, creamer and seasonings. The building has a nice common area with fancy coffees and a decent work out room. We love the location near downtown Evanston and the public transportation to Chicago. We’ve stayed here many times and plan to stay here for all our Chicago visits.

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!

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!

Clean apartment with everything we needed for a family of 4. Space was nice and quiet (no noise from roads or neighbors). Parking was convenient and Michelle was immediately responsive when we needed an alternate parking space when our minivan was too big for the assigned space. Check in was a breeze. Would stay here again

I have stayed at one of Briana’s places numerous times. They never disappoint. She is a great host and always responsive if I ever need anything. This condo is very clean quiet, and cozy. I highly recommend.