Townhome vacation rentals in South Side

If you stay at Cary's place (and you should!), be sure to ask him for restaurant recommendations! He knows these restaurants, knows the owners, and even knows what some of their specialties are! This condo is amazing and we will be staying again.

Alexandra was on top of it and the location was convenient to the best of Chicago. Old Town is safe to walk around and the location was conveniently located to transportation. Really appreciated the parking space that was included.

I can’t say enough good things about this Airbnb! The location was absolutely unbeatable—perfectly situated for exploring Chicago and incredibly convenient for ride shares, which made getting around the city a breeze. The home itself was immaculately clean—truly one of the cleanest Airbnbs I’ve ever stayed in. You can tell Mosmi takes great pride in maintaining a comfortable and welcoming space. This was the ideal stay for travelers who just need a reliable, clean, and comfortable place to come home to after a long day of sightseeing. It had everything we needed, with no unnecessary fuss—just a reliable, peaceful place to recharge. Mosmi was fantastic—super responsive and proactive, making check-in seamless and ensuring we had everything we needed throughout our stay. Best of all, there were zero bad surprises—just a smooth, stress-free experience from start to finish. I’d 100% stay here again next time I’m in the city. Highly recommend!

I stayed here for 3 months to visit Argonne National Laboratory, and it was the perfect place to stay! Supermarkets such as Walmart, Meijer, Tony's and many chain restaurants are around a few minutes away by a car. It takes around 10 mins to get to the Argonne Lab. If you're planning to visit the Argonne Lab, this could be your best choice :) Although it's half-basement, the place is so spacious, so I'm 100% sure it would be better than just living in other small Airbnb rooms. Rose is really understandable easy going person, and she always respect my privacy! And if something happens, don't worry she's gonna text you back so quickly There's a cute dog named Lucy, she is really adorable. If you're a pet lover, you must like it!

One of the best air b&b’s that I’ve stayed in! Petra was a wonderful host, responsive and helpful. The space felt large, clean, and comfortable. Roscoe Village is a lovely neighborhood with lots to do. I highly recommend and would stay again in a heartbeat!

Perfect accommodations for a family of 6. AC was great. Back deck was enjoyable for evening dinner and conversation. Suitable for kids. Always felt safe and parking was available on the street when our truck was too BIG for the garage. It’s Big, so a regular non lifted vehicle would fit. The house was clean and Joyce was available when we had questions. There is a nice grocery story within walking distance and we use the bus to navigate Navy Pier and downtown.

An Unforgettable Experience in Chicago 🌟 Our stay in Chovago was simply amazing. From the very beginning, everything was perfect — the Airbnb exceeded our expectations: comfortable, cozy, and with every detail thoughtfully arranged to make us feel at home. Getting there was super easy and hassle-free. The city’s transportation was also a pleasant surprise — affordable, efficient, and very accessible. The Airbnb’s location was ideal: with a bus stop right on the corner, it was incredibly easy to get to the city center, either by walking or using public transport. We’re leaving with our hearts full of beautiful memories and deep gratitude for the warmth of this place and how easy everything was. Thank you for everything, Chicago. We’ll definitely be back!

Super clean well designed tasteful and nice surroundings. Book this place. Thank you Valerie and Cary.

We are so grateful for Doug and his listing! We had a different air b&b reserved and upon arrival someone was living in our rental and the host was unresponsive. We ultimately had no where to go and we all came from out of state. I reached out to Doug about his listing and he was incredible! He was flexible with our check in, so kind, so helpful and we seriously can not thank him enough. The beds were super comfy, the place was cute and we felt right at home. Thank you SO much.

Second stay at Howard’s place. Easy to communicate with. Great location for Cubs games. Lots of privacy and very comfortable. Rooftop is a bonus!

I booked this space for my sister who is a professional pastry chef. She was in town for my wedding and tasked with creating the wedding cake. This space filled all of the requirements we needed for the project. Right in my neighborhood that I know and love and with a fully functioning and pristine chef's kitchen. The setup could be featured on a food network show, the natural lighting and giant countertops made for beautiful staging. I would absolutely book this space again for a friend or a chef visiting.

This is probably the best Airbnb I’ve ever stayed at, and it has very much to do with the great host that Raminder is. The apartment was clean, spacious, and had absolutely everything we needed. And there was a great amount of snacks & other provisions provided, which also was extremely helpful to us. Raminder was extremely responsive and friendly. I cannot wait to stay here again one day!

We loved this home away from home for our family. Thank you for opening up your well designed home for us. The location is perfect - quiet enough but near Wicker happenings & grocery etc. The hosts were very helpful, responsive, gracious when we messed a couple things up. We really appreciate such a great stay. My only small qualm is the lack of new/clean/working high end appliances we would ordinarily find in a home of this cost. However we booked last minute and didn’t specifically request anything. And found everything we needed to do the job. I highly recommend this Airbnb stay!

My place was being renovated, so I just needed a place to be during the process. This location was great and near my job and my daughter’s school. If needed, I would rent again. Thank you

This place is why I'm hesitant to mediocre Airbnbs a 5 star rating - because this place deserves it! Loved the amenities and layout! Excellent location! Will definitely stay here again if it's available for my next trip to Chicago.

Gabriel was an amazing host who made it very easy to check in and was easily available. The place itself felt more spacious than the photos. It's an extremely functional place. and it was so convenient to the relatives we were visiting in Winnetka, which is such a beautiful town.

Very clean well appointed space. An older townhome, the unit is fully stocked with everything one would need, and parking behind the unit was extremely convenient. Jay was very responsive and helpful. Close walk to train station and restaurants, on a quiet block, with everything one might need.

As Airbnb first timers, Marco & Sarah made a great impression. They were such considerate hosts and accommodating to our situation. They were responsive to all of our questions, from booking through checkout. Their home was clean & cozy; the perfect place to relax and unwind. It was bright, with lots of windows to let in light. The decor was peaceful. The fragrance in the rooms reminded us of a spa, as did the amazing rain shower head in the main bathroom. Guests will appreciate so many amenities, like AC/heat and fans; hand soap/body wash/shampoo/conditioner in the bathrooms; a full kitchen with utensils, gadgets & pans to use, including a Keurig coffee maker and electric kettle; a full washer and dryer w/ detergent; a few games; use of random pantry items; baby & toddler amenities/utensils; even q-tips, tissues and a loofah. Note- there are 2 sets of tall stairs in the unit, but they are sturdy. And, if you come home late at night, you will find parking, but at the end of the street.

Very clean and everything looked as posted. Walking distance to nice restaurants and Walgreens on the corner. Very pleased with the space and everyone was comfortable. Would definitely stay again.

Moh was a great communicator. The space worked out very well and actually felt bigger than what the pictures showcased. The house felt like a home with the small touches and would definitely recommend staying again when in the area.

Great place to stay for a traveling family with pets/service animals. Conveniently located close to train station for those looking into spending time in Chicago without having to pay for parking. Habeeba was very informative and response time was quick. I really enjoyed my stay and what a relief to have a fenced backyard for my dogs to stretch their legs and play. Thank you for being a great host!

Thank you for a great stay. It worked out well for us while attending a conference.

amazing stay! super close to the blue line and lots of restaurants. end unit which made it feel quiet and secluded. fireplace in the back was great!

We had a great stay at the Lucky Penny! Kelly made everything about the stay a breeze, and is a wonderful host who has clearly put a lot of effort and thought into her place and welcoming her guests. Her home is clean and so much fun to hang out in, especially on the rooftop balcony. We loved the neighborhood, and were easily able to get to attractions around the city. Overall this place is an absolute gem, our kids had a blast and said if we ever come back we 100% have to stay here again!