Kid-friendly holiday rentals in Downtown Chicago

Jennifer and David were awesome hosts! So friendly, helpful and accommodating! I had some of the best-ever homemade cookies that Jennifer baked! I'm hoping to make them my Evanston place when I return to the Chicago area annually. Thank you, Jennifer and David!!!

This place was perfect for two of us! Everything about the description was accurate. It was very clean, super easy to access, and in a perfect spot-walkable to tons of restaurants, coffee shops, and even a few gyms we tried. Water pressure in the shower was phenomenal. Neighborhood felt safe for late night walking to and from restaurants. Hosts were communicative without being over-the-top. Would book again in a heartbeat!

Wonderful home close to train station. Very convenient and cozy. Would recommend!

This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!

One of the best Airbnbs I have stayed at. It was beautifully decorated and super clean. Had everything I needed to feel comfortable and at home. The host was extremely responsive. The parking was a bit difficult but would not deter me from staying there again. Very close to downtown, about 10 minutes. Highly recommend.

Great

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.

Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!

I was very impressed and pleased with all of the thoughtful details and extras like Keurig pods, filtered water and parking stickers. The space was cozy and perfect for our small family. It had every possible amenity needed to make ourselves at home for a week and cooking was a breeze. The location was ideal both due to the proximity to our daughter’s place, but also very quiet and walkable to everything you need including restaurants, stores, light rail and bus lines. Leigh-Anne was super responsive and flexible. The only word of caution would be that guests who are very tall (like over 6’) might find the ceilings too low, though they were perfect for us. We would definitely stay here again on a future trip.

A-MAZ-ING stay! My wife and I had such a blast in Chicago. GOGO was very kind and inviting, good energy! The place was exactly what we wanted with all the amenities. Sparking water in the fridge which was a treat after waking 18k everyday. As a runner, there was plenty of sidewalk and things to see. I recommend running up LEAVITT to 18th street and take 18th down for a nice 3 to 5 mile run. The L train “pink line “ was close and walking back at night we felt relatively safe. I would high recommend staying here in Pilsen area the next time you are in Chicago. Mahalo

Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!

There is no way I/we can do a review of Elizabeth's beautiful apartment in just 1,000 characters. Met Elizabeth personally, made a wonderful connection. It's the most awesome airbnb we've ever stayed at. The apartment has been beautifully remodeled. As a retired general contractor, I was very impressed. The neighborhood is fantastic; great for walking, shopping, and there are restaurants galore. The location is fantastic for touring Chicago. The neighborhood is beautiful with lovely architecture and interesting shops. There are lots of families; couples walking, biking, babies-buggying. We enjoyed walking around the neighborhood after a walk to dinner or lunch. The bed/bedding is very comfortable and we slept very well. Great temp control, lots of windows, and a 65"flat screen TV. The bathroom is large and airy with a walk-in shower. The unit is very quiet, with dual-pane windows and black-out shades for sleeping in late. Stay here for the best Chicago experience.

Well kept, quiet environment. Host is responsive.

If it’s open. Book it! You won’t be disappointed. No matter where you’re going in Chicago or surrounding suburbs this location is a winner. Easy access to both CTA and Metra Union Station and the host are the best!

El departamento es muy pequeño pero tiene lo necesario para una estancia de pocos días. Es un edificio antiguo pero bien conservado. El departamento estaba limpio y la cama es cómoda. Está bien ubicado, con excelente conexión a todos los medios de transporte y cerca de muchos de los sitios importantes. El único problema es que el tren pasa a pocos metros y es bastante molesto. El otro problema es que el wifi no anda muy bien. Es muy lento y por momentos se corta. El equipamiento de cocina es muy limitado pero alcanza para lo básico. Además solicitamos una tostadora y enseguida nos trajeron una nueva . En ese sentido, Ping tuvo una excelente disposición para responder y resolver lo que necesitábamos. En síntesis, es un lugar recomendable.

Erika’s place was so convenient for going to University of Chicago Convocation activities. Close enough to the school (beautiful 25 min walk) yet far enough from the convocation traffic! I was able to always find car parking within one block from the airbnb. The place is bigger than the photos suggest. The living room is especially comfy! Perfect for 1-2 people.

We loved our stay at Danny's place! This was our first time visiting Lincoln Park, and the location of the home was perfect. We walked to restaurants, the Lincoln Park Zoo, and the beach. We appreciated being able to have our dogs with us and found the area very dog-friendly on our walks. Danny was kind and thoughtful with all the extra touches and responsive communication. He even caught us in person to make sure we had everything we needed. Our family felt safe walking in the neighborhood day and night. We even took the bus to downtown Chicago, which is only a few miles away. The house itself was very clean and large - our family of 4 plus 2 dogs had plenty of room to spread out and feel comfortable. We highly recommend the home to others and hope we can return again someday!

We had a great time here. The place is really cozy and located in a nice neighborhood with plenty of stuff in walking distance. Totally worth it.

Great location and responsive host. The amenities in the place are great and the bed is amazingly comfy. The airbnb was a bit dusty everywhere (the bottoms of our feet were black after walking around barefoot), but that seems par for the course for basement apartments that just hang on to dust.

Great location and property!

Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.

Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai

This is the second time I’ve stayed at this condo, and as always, it didn’t disappoint! It’s close to great restaurants and lots of things to do. I absolutely love the shared outdoor space as well.