Guesthouse holiday rentals in Chicago

Place was fantastic. Everything as advertised. Niles was a pleasure to deal with and even leaves some nice extras for you too. One of the most comfortable beds in any B&B I’ve stayed in. Perfect for business or pleasure. Five stars all the way. Definitely using again!! Parking too!!!!

Liz’s place is very special indeed!! It is beautifully decorated, immaculately clean and cozy. It’s walkable to a great supermarket, downtown Wheaton and Wheaton College. It really felt like a home away from home. I’ll be back!

Mat is an amazing host. His property is incredible and he's extremely responsive. Would definitely recommend this airbnb!

We had a great time here! We really liked the area it’s in, and finding parking was easy. The house itself self is very cute and clean. Thanks so much for a great stay!

Very nice place and very comfortable. Only a block away from a street full of shops, restaurants and bus stops. It was also about a 10 minute walk to the blue line. Very quiet and secluded spot as it was behind the main house and had an alley behind it.

We've stayed at quit a few places near Wicker Park and the Ukrainian Village. Each was unique and charming. Joe's place is equally so, and what really made this special is the welcoming atmosphere and astonishing sophistication. Joe has obviously put a lot of work into making the coach house a space that is cool and comfortable. The space is quiet and feels remote, but just a few steps from some of the greatest coffee spots and eateries in the galaxy. We went to a show downtown and it was super easy to get to the metro station. Parking was great. Joe and his family are very helpful. (and we LOVED the shower & scrumptious towels). If you love coffee, Joe has the setup ready to go for you. This is a gem of a find. We look forward to staying again.

The location was perfect. Jury steps from Wheaton college. We stayed here during the Wheaton College Christmas Festival which we were able to walk to. Angel’s place was clean, had a Keurig with different choices, and filtered water. We had everything we needed for a short overnight stay. Thank you for a great stay!

thank you for the great place to rest

Lovely place to stay! Reminds you of home in a quiet neighborhood <3

We felt right at home at Daniel’s place. We had more than enough space for a family of four. Even though we had a night time arrival, self check-in was quick and easy due to Daniel’s detailed instructions. We spent most of our days out in the city, but it was so nice coming back to a quiet, warm, and cozy place in the evenings. I would highly recommend this place for UChicago alumni or families who are doing a college tour. It was a walk down memory lane for us visiting so many familiar places after so many years. 57th street is a very short walk from the Airbnb location. Location is so convenient to get around to many must see spots. Tip: If you need an evening coffee fix, go to Plein Air Cafe on campus. This cafe closes much later than other coffee shops in the neighborhood. The cafe is also adjacent to the Seminary Co-op and FLW’s Robie House, and has outdoor seating.

My family and I stayed at Casey and Esteve's place for 6 days. The hosts were responsive from the time of booking until the end of our stay. The location was great, 10-15 mins walk from public transportation which made Chicago downtown easily accessible. The house was clean and fully stocked with all the basic amenities plus some added bonus (coffee/creamer/sugar for the coffeemaker, toiletries, etc). The bed and pillows were very comfortable as well. My family and I will definitely stay again and would highly recommend this listing.

Due to a family emergency, I wasn't able to stay at Robin's place. However, Robin was very proactive, responsive, and prompt in communicating. Also, I know Evanston pretty well, and Robin's place is in a great area that is very walkable with lots to do within a short walk.

Emilia's place was a nice retreat for my 4 days of training in Chicago. The location was great, near the training and not that far from O'Hare. The place was very clean, all amenities that I needed, and I will plan on staying here my next trip to Chicago. Thanks Emilia!

I had to do a little teleworking on my trip and I was worried about how that would work out. Turns out it was easier to telework from Christina’s place than my own. It could not have gone smoother. I would absolutely stay here again!!

I recently stayed at this charming Airbnb, and it was an excellent experience from start to finish! The property is beautifully maintained, with a stylish interior that perfectly reflects the vibrant character of the neighborhood. The space was spotless and equipped with everything we needed for a comfortable stay, including a full-sized kitchen, cozy furnishings, and thoughtful touches like local guidebooks and snacks. The location is unbeatable. We loved being within walking distance of trendy cafes, restaurants, and unique shops. Public transportation was also conveniently close, making it easy to explore other parts of Chicago. Our host was outstanding—responsive, friendly, and eager to ensure we had a fantastic stay. They went above and beyond to provide recommendations tailored to our interests, which made our trip even more enjoyable.

By far the best place we’ve stayed in the Chicago area. So close to the airport, super easy check-in and check-out. The place was warm and quiet and had great towels and amenities. Couldn’t ask for more!

Comfortably fits 7 people! Being able to park on the property was a huge bonus!

Adorable place. Very quiet neighborhood. Everything you could ask for in a rental.

This was a very nice place to stay. Would recommend. Highly responsive and kind hosts.