Vacation rentals with outdoor seating in South Loop, Chicago

Staying at Matt’s Air BnB was a fantastic experience. We stayed with our two kids and another couple and the space was perfect for our group. The spacious, fenced in yard made for a great hangout space for our toddler to safely run around. The house looks exactly like the pictures and was extremely clean. We will definitely stay here again! Thank you, Matt!

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!

Great clean place

O espaço da Janice é extremamente aconchegante. A cozinha é super equipada (geladeira, fogao, cafeteira, panelas e demais utensílios... alem de manteiga e temperos básicos). O quarto é lindo e a cama super confortável. O banheiro estava limpo e havia itens de higiene de ótima qualidade, além de um excelente secador de cabelo. A televisão era grande e a sala super confortável. Amamos tudo. Quando voltar à Chicago, será a minha escolha!!

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.

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!!

I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

The house is very beautiful. My family and I loved the place and how spacious it is.

We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!

Einfach nur wundervoll. Das war eine der schönsten Unterkünfte, in der ich je war. Die Wohnung ist total liebevoll eingerichtet. Alles war super sauber und ordentlich. Es gibt sogar Zahnbürsten, Zahnpasta und eine Schlafmaske, falls man sie benötigt. Die Küche ist auch super ausgestattet mit allem was man braucht. Der kurze Weg zur Metro war ebenfalls sehr praktisch. Wir würden definitiv wieder kommen.

We truly had the best time staying at Alec’s. The space is lovely, comfortable, and has everything you’d need. The outdoor spaces were beautiful and private with a high fence surrounding it. We enjoyed spending time by the fire and the neighborhood is great. Our favorite part by far were Alec’s two lovely pups Molcajete and Lobita. They were absolute ANGELS and made us so happy- we hated leaving them. Alec was a great host- super communicative, friendly, and just what we needed. When we come back to Chicago, we’ll definitely stay with him again.

5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!

We had a great stay in downtown Chicago at this apartment! Great views and we enjoyed having access to the pool since it was a beautiful weekend.

Loved everything. Great location. Really felt warm and comfortable. Nice touches—candy jar, fruit. Definitely would stay 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.

We really enjoyed our stay at this apartment. I stayed here with my sister and my parents, and the four of us were very comfortable here. We made breakfast one morning and had everything we needed. The Red Line L is literally around the corner and a 10-minute ride for $2.50 will spit you out downtown. We were also delighted to discover multiple bakeries and coffee shops within a 5-minute walk. The neighborhood overall felt very safe and walkable. We would definitely stay again!

Super séjour nous étions 5, bien aménager,équipement parfait, très propre, hôte très accueillant et réactif, à 10min à pied de la Green ligne, quartier très calme supérette à 15min à pied.

Good location. Condo was very clean with comfy beds. There are 3 flights of stairs to get to condo- no problem for us but be aware

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.

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.

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.