Holiday rentals with outdoor seating in South Loop, Chicago

We had a great stay. The house was perfect for our group - 4 adults and 1 baby. Very clean, with great facilities. The wireless chargers were so helpful as we were international visitors. Also, the provision of tooth brushes, mouthwash and razors in the bathroom was a great bonus. Plenty of towels, comfortable beds and lovely location near the Prairie path made it a wonderful stay.

Best Airbnb we’ve stayed at yet! Thanks to Giovanni we were able to visit with our family for Easter. The previous Airbnb we booked cancelled on us at the last minute; hours before we were set to arrive in Chicago from Detroit. The space was just like the pictures. It was clean and we felt right at home. The backyard was spacious and is fenced.

2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂

Thanks so much for everything! I have a reactive dog that has never been left in a doggy daycare, and Miranda helped me experiment to find the right fit for him. I was able to attend my conference and I am very grateful. Great place and great host!! <3

Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.

rob and sue were great hosts. easy, timely communication. the house has everything you’ll need and is spacious and quiet, despite being close to some busy streets. walkable to diners, restaurants, and some shopping. . will definitely book again.

BART and Team were very helpful. The place is great for families.!

Adam’s house was amazing, the location, the decor, the back yard. Everything was clean and comfortable and he went above and beyond to help us with a random request. Highly recommend.

Great place to stay, just the right amount of space for two couples and really well located for exploring the neighborhood. We particularly enjoyed the large deck, very nice in good weather!

We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

A very nice and welcoming place to stay!

me and my fiance stayed just a few days and I didn’t want to leave! The space was even better than expected. Having almost everything you’d need to cook, plenty of towels, clean bedding. It was so clean and beautiful inside and the view from the balcony was gorgeous. Felt just like home. The neighborhood was very nice and peaceful as well. We will 100% be back!

I was there with 2 friends for a guys weekend and a Saturday Cubs game. The stadium was walkable and Terry was great. We had a small hiccup when checking in but was completely my fault. Terry was home and helped us get in. For what we needed it was perfect.

We really enjoyed our stay! We really like Roscoe Village and this apartment was perfectly located. Close to shops, coffee and restaurants. The check in process was easy and the apartment was well appointed with everything we needed. Parking was very easy as well. This was a great find for us and we will plan to visit again!

I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!

Great place, beautiful attic and great amenities from host!

Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

This was a great place to stay while in town with friends for a weekend! Walkable to great restaurants and shops, and the place was extremely clean and filled with natural light. Comfy beds and good shower pressure. Would stay again!

Our group had a wonderful stay at Alex's place! He was so accommodating setting us up for our stay, allowing an early check in, getting parking passes and a crib set up prior. We appreciated his quick response times and thoughtful communication - it is apparent he wants his guests to have a relaxing and enjoyable stay. We recommend this place to anyone! 10/10.

It was exactly as it was pictured except the front door is adjacent to a beauty salon and a bit hidden at first. The place was immaculate - very clean and the kitchen in particular was excellently appointed. It is on the third floor in an older building so there are stairs. The building was quiet. With gated and lit parking provided nearby our vehicle was safe.

Great location. Accommodation just as described-fun decor. Comfortable beds.

Under the category of actions speak louder than words, I have stayed at Allan's place about five times, and it remains my first choice when visiting Chicago.

Adrian’s condo was perfect! We had the most incredible stay! Gorgeous design, comfortable beds, great bathrooms, felt very safe, amazing communication, etc! So impressed! We will definitely be back and will recommend to family and friends!

Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!