Holiday rentals with outdoor seating in South Loop, Chicago

We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

We enjoyed our stay. The place is located in a convenient location close to many shops and restaurants and just around the corner from an L station. The home was very spacious and comfy for our short stay. You can hear the train in the house however it wasn’t bothersome even for our toddlers when they were asleep.

We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=

Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

My husband and I really enjoyed our stay. Arlene was super proactive with communication and made everything very clear. It was easy to find and get inside. The bed was also extremely comfortable. I was really impressed with the location and the space. Extremely walkable to everything we needed for a wedding weekend at Tied House.

We had a great stay at this place. The location is very nice. Get to be outside of downtown still while close enough to visit whenever you’d like. The retro vibes of the home itself is very cozy and unique. Will definitely book again if we ever come back.

This place was amazing! My friends and I were scared about the parking at first but it was pretty easy. Instructions were really clear and the host was really amazing with their communications. The area that the home was located in felt safe and is pretty quiet. The home itself had great designs and decorations which made the home feel really cozy to me. I would definitely stay here again and I recommend it to others who are traveling to Chicago.

I loved the little cottage. Quiet neighborhood, felt safe. Restaurants were walkable. Reached out to Marilyn for a breakfast recommendation and checked out bacon and jam, amazing. House was easy to find. Clear instructions. Felt at home.

What a delightful place this was to stay at! Loved the wood floors and comfy bed. Peaceful and safe area for a solo business traveler. Plenty of parking in front. Deck was adorable with the flowers. Had a full kitchenette stocked with tea and coffee. Mindy was so responsive and kind!! One of the best places I’ve stayed at!!

Khong was a great host and super communicative. The place was as described. Everything was clean and the fenced in yard was a nice bonus. The drive into the city was anywhere from 30-45 minutes depending on traffic. There is a garage to park a small car in, I was able to find parking on the street as well. Something to note is that this is in the south side of Chicago so it’s not the greatest area. There was a lock on the gates to get to the house so I didn’t necessarily feel unsafe. Overall, a great stay.

One of our favorite Airbnbs in Chicago, it has a great central location and great street parking (with a permit). It's cute. clean, and quiet. I highly recommend!

We loved our stay! It was so clean and very close to public transit! We navigated the trains to and from Cicero into Chicago NP! We will definitely be back and we would definitely recommend staying at this Airbnb!!!

I loved this place. Christine was such a great communicator , took initiative and very prompt to respond to text and resolve any issues, which we had none. She contacted me a day before stating they had HVAC issues but would try hard to resolve it Before we arrived and it was! Loved the location, loved the decor, 2 bedrooms so my brother and I enjoyed our separate spaces . Easy and accessible. No issues with parking. Low key , chill. Never saw Christine but she responded within 15' of text through the airbnb app, Chicago is chilly right now, the unit had extra blankets, floor heaters and a wall booster to circulate the heat and great instructions in the house manual for working the wall thermostat. Great coffee bar/area. Would recommend! My impression of the space was Bohemian Chic and felt like home. Thank you! Her neighbors were also very considerate . I was a bit disappointed it was raining because we never got to utilize the outside patio/balcony!!!!!

This was my first time booking with Airbnb and all I can say is that it could not have been a better experience! Aaron was so nice and beyond helpful. The apartment was the perfect size for my husband and I. It is in a good location, we were able to get to anything we needed or wanted with just a short walk. Not only that but the building itself was so cool, the lobby is beautiful and the amenities were spectacular. We ventured to the rooftop many times because of how nice and peaceful it was. We attended a concert at the Aragon Ballroom and it’s the first time we’ve not stressed about how to make the trip there and back. It was maybe a 3-5 minute walk at most! Overall it was beyond what I was expecting. If available, anytime we will be in the area this will be our first choice!!

great location. very responsive. Definitely would book again

Sarah’s place was lovely! We had a wonderful time — it was within walkable distance to main attractions, and the neighborhood itself was safe, nice, and clean.

Planned a trip to Chicago for a weekend get away and Michael’s house did not disappoint. Free parking with unlimited parking passes, probably the most friendly/sweet neighbors you’ll find and just a very beautiful home 100% recommend very close to the green line train which we used to get to the loop every day book this house before it’s gone!

Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

This is our 3rd time staying at Thomas and Cynthia place. We would have it no other way. Home away from home every single time.

This was a fabulous place to stay! My brother and I could easily walk to the "L" and head downtown. The pizza place right downstairs was delicious - we ate there twice in three days! The beds were comfortable, the couch and living room set up was cozy. I would absolutely stay there again!

One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

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.

We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!