Vacation rentals with outdoor seating in South Loop, Chicago

Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

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.

Loved everything about this place! I cannot say enough good things about my stay. I will say, it is quite far from Chicago. It didn’t quite matter for me as I knew I wanted to find a place away from the city but on a week day it is about an hour or so from downtown. The place was quiet, pillows insanely comfortable, amazing shower, kitchen was great and well equipped, clean washer and dryer, easy to get in and out of the place. Great place to stay.

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.

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.

An absolutely fantastic location and cozy airbnb for my sister and I’s trip to Chicago to see Beyoncé. Tons of restaurants a short walk and drive away, there’s a train station 3 blocks away as well, and Dark Star coffee was a great rec. Loved the airbnb, it may look small but it is so spacious. We each had our own amount of privacy and didn’t feel on top of each other. Only thing that I would recommend is packing on the lighter side for there are quite a few steps to climb to get up to the airbnb. But all in all worth it. Definitely bookmarking their place for future Chicago visits.

This place is exactly as you see in the pictures. Edward is a great host and I definitely would stay here again and I highly recommend it. I don’t even have one negative thing to say about the place. Thank you Edward for letting me stay in your beautiful home.

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!

I loved everything about my stay ! Very nice and clean and the host were amazing

Kasey and her husband were awesome host!!They were kind & responsive! My friend and I come during a time in winter and Kasey was very quick to keep us warm! Although they do have a child it was very rare when we were disruptive by noise! Love the vibes of the Airbnb and the fact that I felt like home says something! I definitely recommend staying here. Such a co beautiful and peaceful area as well.

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.

This is a really nice spot. Had everything we needed. Lot of small shops and restaurants nearby. If you like to walk (which we do), downtown Chicago is only a couple miles away. It’s also not too expensive to uber there either. Had a great time!

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!

Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!

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!

Cody’s place was a perfect hideaway from which to venture into the city, and both far enough away to be peaceful but close enough to a string of good restaurants and cafes to be walkable. Check-in and house instructions were comprehensive, Cody himself was proactive and communicative, and the hot tub was a major plus on cool nights. Looking forward to another stay!