Townhome holiday rentals in Near North Side, Chicago

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.

This home in Chicago was exactly as advertised. Perfect for a girl's weekend in Chicago. Plenty of space for sleeping, large bathrooms with plenty of mirrors to get ready. The house was well stocked with everything we needed for a perfect weekend. The location was great too. was able to walk to bars and restaurants or take short Uber anywhere we needed to go. Having off street parking made it even better for out of towners who drove to the destination. I would definitely book again when traveling with a large group.

Great location, would stay again. Very walkable to metro station and Fulton Market. Place was quiet and safe. Easy access instructions, simple to follow. Host was very clear with instructions and responsive.

Had a great stay at Steve's place with my friend and our 2 dogs. Nice quiet neighborhood.

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!

I know people read the latest reviews, so I am always writing the same thing. Petra's place is a gem, my favorite in Chicago (I have to come to work 6 times a year). It is extremely clean and confortable, you have 2 very spacious rooms, closet and drawers to unpack, nice bed. No kitchen, but you can microwave meals and the restaurants in Roscoe Village are great. Bus nearby and Metro 15mn walk.

My partner and I were visiting Chicago to celebrate his birthday and stayed here about 2 weeks ago. I'm a very experienced traveler but this was my first time staying in an Airbnb since 2019, and I love the comfortable feeling of being in a home while on the road. This spot was very conveniently placed around Logan Square and the neighborhood felt safe. The host was very helpful, super quick to respond, respectful and gave us tons of itinerary recommendations. 💯 I liked the medieval decor around the apartment. It was very suiting for our trip since we went to Medieval Times Dinner and a dungeon synth show during our stay in Chicago. ⚔️ I will be using Airbnb more often in the future.

We had a fantastic month-long stay with Tony and his family. Even before our arrival, Tony was incredibly responsive, allowing us to drop off our luggage before check-in so we could explore the city. The room and bathroom were spacious and separate from the main living area, which we appreciated. The kitchen was well-equipped with everything we needed, and we loved chatting with Tony and his wife, as well as interacting with their adorable baby. They always provided excellent recommendations for restaurants, local attractions, and transportation tips for getting around the city. The location was ideal, with a grocery store and great restaurants in Old Town all nearby. Bus stops and train stations were just a short walk away, allowing us to get around the city with ease. This was a wonderful experience, and we couldn't have asked for better hosts! We know we can reach out to them if we visit again, and we will certainly be back!

This was very comfortable and perfectly located. Parking was especially helpful. It really is a home, unlike many Airbnb that are investment properties, and you could feel it. Thank you Marie.

We absolutely love this stay. As a full time traveler, this has been one of my greatest stays! We were actually looking for upcoming dates to utilize the spot again, as I am in and out of the area frequently, but it is filling up fast! I’d recommend this place to anyone and I’m pretty picky. We only wish for blackout curtains in the main bedroom. Place is 10/10

We had a great stay and enjoyed the apartment!

You cannot pick a better place in the area. In fact I book here at least once if not twice a year. She is the absolute best person and so kind and accommodating. If you have been thinking about booking here, stop thinking and book!

Well, It is certainly, a nice, peaceful, and cozy house, I had a very comfortable rest and a delicious coffee every morning. Thanks to this, I could fulfill my commitments of the day in Great Lakes, IL. Simply Great! Thank you Habeeba!

The place was very clean, easy to find. The host was very responsive and friendly. Would definitely recommend this place if you don’t have issue with no bathroom in master bedroom.. Great place and would stay again. Lamar

In town with friends for a show. The home accommodated us perfectly and Karen was great!

Excellent stay and service.

We found Jay's place to be an excellent value: great location close to public transportation & within walking distance of good restaurants (& a terrific Italian bakery). The kitchen amenities were excellent, & the whole place seemed to have been renovated recently. We'd definitely stay there again when visiting Chicago.

Had a nice stay at this location. Host was very responsive to any issues. Space is very well stocked for everything you need and the location is fantastic. Outdoor space is a great plus as well.

Overall we had a great experience with this rental. Some of the vents were heavily dusty and would be only area of improvement I’d encourage. To the guests, a warning is there are stairs immediately upon entering, so don’t pack super heavy. Otherwise, the listing matched its description and my friends and I enjoyed our stay.

We were coming in for a funeral and had much of the family with us. The place was perfect for gathering and everyone found the accommodations comfortable and homey. It’s in a nice, safe area of Oak Park, near several Frank Lloyd Wright homes.

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!

I appreciate the quick responses to all my inquiries. We stayed in January and there was some snow and ice, it was taken care of so quickly! Before we realized there was ice, there was salt and clear drives and sidewalks! Beds and pillows very comfortable. The entire stay was a “staycation “ for us to be closer to visiting family, this suburban location was perfect . All appliances were new and felt like an upgrade to what we have! Would definitely stay again

Gabriel’s home was an oasis for a girls weekend. The home itself was the perfect size and in the perfect location. We spent the entire weekend walking to 2 cute shopping districts with great restaurants and to the beaches at Michigan Lake. We also loved walking the neighborhoods. Gabriel made us feel right at home.

I really can't think of anything I would change about this airbnb. Location was great with lots of shopping, restaurants, and coffee shops within walking distance. It was very clean and spacious with all the dishes, towels, extra bedding, etc that we could possibly need. I loved that the bedrooms had ceiling fans and beds were very comfortable. It was also a huge plus that there are two bathrooms with showers in each. Hien was very responsive when I had a couple questions. I definitely hope to stay here again.