Apartment holiday rentals in Downtown Chicago

My group had an incredible stay. we came stocked up with coolers and boxes of groceries but there was a target across the street for any supplies we forgot. so much to do in walking distance! the views were incredible and we spent probably half the time just hanging out on the balcony! the people at the front desk were incredibly helpful and friendly as well. cant recommend enough

Terrific location, terrific space, terrific views. Hosts were responsive and flexible. Looking forward to our next visit.

My stay at Sean’s was exactly what I needed…..a clean, quiet, comfortable and peaceful place, being in Chicago for an active, somewhat stressful weekend. The location in beautiful Old Town was perfect, within walking distance of where I needed to be. I had the added bonus of meeting Sean and Stephanie, which is becoming more rare in my Airbnb travels, both very friendly and accommodating. All communication was prompt and helpful. I would highly recommend.

This is my second (maybe 3rd?) stay at one of Jordan & Jeremy's properties and the experience is consistently pleasant. Listing is accurate, place is cozy and clean. I wish all AirBnBs were this consistent!

Great price and great location. Room was as advertised. It’s always a bit tricky checking into a secured apartment building, and there were a few hiccups, but overall things went smoothly thanks to support from Ben’s team and the building’s concierge.

Sonder was so quick to reply to questions I had before I booked but when I was locked out of the Airbnb 2 hours after check in they still had no alternative password for me to enter. Overall the location was great. Cleanliness was exceptional. And so much to do with in walking distance!

great location. very responsive. Definitely would book again

We were a family of four that had a wonderful stay at Kasa South Loop. The apartment was very spacious (especially living room and master bedroom. The second bedroom with twin beds was a bit small). We did not use the kitchen but it had all the basics, including coffee capsules which I didn’t see until the last day (they are in a basket!). The views were amazing. The neighborhood is quiet and walking distance to grant park, art institute, etc. we would stay here again.

Thank you so much. Looking forward to staying at your place again.

Clemente's place was in a great location central and walkable to many great areas and the train station, it was clean, it was easy to find, and it was comfortable. The beds were comfortable too, the A/C and heat was great, and the kitchen was well equipped. I would definitely recommend his place as a nicely affordable 2 bedroom in close proximity to the sites and restaurants.

Our second stay here-- all is wonderful!! Well appointed space, fabulous bed and pillows. Everything you need is in the kitchen. The location cannot be beat -- across the street from the park. Would absolutely come again!!

5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!

Thank you Nicole and Matt for our amazing stay at your home. We wanted to be in an area that not only had the comforts of home but also close to restaurants, night life and public transportation. The gated entry into the courtyard is lush with flowers. The home is modern and spacious with a comfortable bed, large closest and washer/dryer. The kitchen had all that we needed although we never needed to cook. It had all that you could want for a relaxing, carefree stay! We were steps away from some of the best restaurants, bars and nightlife. You can walk to so much that Chicago has to offer. It’s a short walk to the Lincoln Park Zoo, the beaches at Lake Michigan, the shopping and fantastic dining in the Gold Coast. We also took in a show at Second City which was so close-by. Thank you to Nicole and Matt, they were great hosts - very responsive and flexible. They left clear check-in/check-out instructions. We thoroughly enjoyed our stay here and would not hesitate to stay here again!

Our stay at Chicago Hospitality Club was great! It was so quiet! Beds were comfy and there was so much space! We enjoyed the outdoor space as well. The views were stunning!! It was very close to the red line and walkable to Lake Michigan, Buckingham Fountain, the Bean, and the aquarium. Just a mile from theatre and shopping on State Street. We found a lovely Italian restaurant in Printers Row on Dearborn, named Sofi. We had a couple issues that came up with the space and the Hospitality Club was super responsive and went above and beyond to bring resolution.

The apartment was impeccably clean. Was traveling for business had everything needed. It is loft style with open bedroom ceiling. Restaurants nearby

The apartment is beautiful and just as the photos showed. I loved the spaciousness of the kitchen/dining area/living room. Nicely decorated. The beds were a little too firm for me and quite high, perfect for tall people, but us 5' 0"ers need to crawl up (you'll get the hand of it). Hubby loved the bed, I loved the sheets and bedding, very comfy. Rooms are also very spacious and the light in all rooms is great because of the large windows! Host provided ear plugs for the noise (near the L), but we didn't need them... the sounds really didn't bother us. Only noted issue is you might want to bring adult size towels with you. The 4 in the apartment are all hairtowel sized, kinda small for full body drying. Plenty of wash cloths, though. Overall, our stay was verycomfortable and I would book this place again when we return!

It was a perfect place to stay for a few days. The skylights and all the beautiful plants really stood out. We really enjoyed the coffee bar to start our mornings. Lots of indoor and out door space. The room had the ability to adjust temperatures for each room. Great communication on check in etc.

Run, don't walk, to book this location for your Chicago stay. The view of the Chicago skyline is perfect, even better than if you stayed in Downtown itself, sometimes all you see is the wall of another building and no view. The instructions how to get there are very clear, if you're a little intimidated like I was about going to a big city never fear. The instructions are clear, easy to follow, and transit is close by to take you wherever you want to go. Overall great trip, thank you!

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.

Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!

David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

Great place nice views , communication with host very smooth !

Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.