Townhouse holiday rentals in West 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.

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!

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 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!

Wonderful! It is the perfect place for a family. Everything was done meticulously.

We had a wonderful stay at Marie’s place! The location was great, on a nice quiet street close to downtown. The home is beautiful, and very clean. I would definitely stay again if in the area.

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.

The home was cool and eclectic and was in a great area: so close to Wrigley and all that the area had to offer.

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.

We had a lovely stay at Steven and Lisa’s place while we were in Evanston for our son’s graduation. The place had plenty of room for the 5 of us and we felt right at home. There’s plenty of storage space and helpful amenities. The back patio is very peaceful. The location was convenient to Evanston and the city of Chicago. The neighborhood is peaceful and really beautiful. Thanks for a great 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 was spectacular! Very clean and organized space. All of the various amenities were available to use in the space which was lovely. We were in town to elope and so we only stayed two nights but we would definitely stay again! The beds were extremely comfortable and the AC worked well which I appreciated since I get very hot while sleeping. The area was also very walkable to different shops and restaurants. If you want a very luxury feeling space in the area then I highly recommend Rain’s place!

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.

Our family had a wonderful time and loved the neighborhood. It was near many places we wanted to visit and also near public transit. Our boys enjoyed the "movie theater" in basement and thought they had quite the special place to stay. We also enjoyed grilling out on the private patio. It was a nice weekend getaway.

Perfect Chicago unit in a great location. Walking distance to coffee, playgrounds, and great restaurants. We had no problem finding free street parking, even late at night. Host were very accommodating and great communication. Would love to stay here again!

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's townhouse was absolutely beautiful! One of my most favorite places to stay. Place looked brand new and decor was top notch! Large comfortable bed and nice bathroom and kitchen. It was literally minutes away from nice restaurants and shopping. Would definitely love to stay again 💕

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!

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!