Holiday rentals with outdoor seating in Old Town, Chicago

We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !

Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

I enjoyed my stay here which enabled me to be close enough to Northwestern’s campus as I worked on a writing project. Being minutes from downtown Wilmette was a plus—be sure to check out Saint Roger’s Abbey bakery for wonderful French pastries! The house was neat, tidy, and matched the description. I also appreciated the record collection!

Had a great five night stay, still only scratched the surface on what this fun neighborhood has to offer. Cute little house, squeaky clean and well organized and quiet even though close to anything you would want (including blue line). Host team super responsive, would 100% stay again!

We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

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.

Mindy & Tony’s place is well located - easily walkable to transit & the cute West Town neighborhood restaurants & shops. The room was very nice - I especially liked enjoying sunset tea on the wisteria-covered deck. Thanks for a cozy stay!

Even better than described. Good out door decks, comfortable beds. Parks across the way, quiet area, felt spacious but also next to a ton of stuff to do. Not congested but also close to everything- like a few mins walk. Song is wonderful and clear. Perfect communication.

lovely stay in nice neighbourhood with great bars and restaurants close by . Easy access for train to city.

I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.

The space is exactly as described. Loved how close it was to public transportation. The space is great for a weekend away.

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!

Caroline and Rey are great hosts. Great setup in the heart of a fun Chicago neighborhood. Short walk to Wrigley. Really enjoyed our stay. Caroline genuinely offered for us to call with any questions or concerns. But it wasn’t necessary. We were warmly greeted. Nice family. Great apartment. Thanks for a wonderful visit.

Absolutely loved staying here! The apartment is stunning—stylish, super clean, and thoughtfully put together down to the smallest detail. The location couldn’t be better, and the host was incredibly kind and quick to respond to anything we needed. I’ve been staying here for years and will definitely come back! It’s the perfect apartment to explore Chicago.

Matthew's home was incredible! It was a beautiful and comfy space and immaculately clean. The instructions he provided to check-in, where to find things, etc. were very accurate and well thought out. There were more amenities than mentioned in the listing. It really felt like staying in a real home and not a normal Airbnb rental. Matthew was very responsive and really made our stay special. He really went above and beyond any host I have seen before. We were in Chicago for my daughter's college graduation and he made a personalized welcome and congratulations sign in the kitchen just for us. Additionally, on our first morning, there was a chance of rain in the area and on his own, Matthew went out and purchased and provided umbrellas in case we needed them. Above and beyond hosting! I can't recommend this home highly enough!

Great place! Everything was clean, in a good location and they communicated well.

John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!

We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

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.

Awesome spot Kelsey has! We loved the location. Easy trip to basically anywhere in Chicago and safe area. Thanks for having us!

Our group of 4 had a wonderful stay: Incredibly communicative host, beautiful and Blue Line-accessible property, lots of local eateries within walking distance, and very spacious rooms throughout the home. Hans was super helpful with our group's late check-in time and was always accessible. Definitely would recommend for both small and larger groups, and we hope to visit again in the future!