Apartment vacation rentals in Old Town, Chicago

Niki's place in East Village was a perfect place for us - close enough to downtown Chicago, in a charming neighborhood with lots of good restaurants. Easy to walk around, get Uber or catch a train. The house itself is old and quaint, with a lot of character. Large windows bring plenty of light into the house. We did not use the kitchen, but Niki had ramen and other snacks on the shelf if we wanted. The bathroom was small, but it was not a problem for us. The house has a small front and back yard with trees, plants and ivy. Overall, we loved staying at Niki's place. We highly recommend it!

We enjoyed the outdoor space and the indoor space was perfect for our trip. I loved the details of the construction.

This apartment is ideal for a couple staying in Roscoe village. Close to many pubs, restaurants and shops . The balcony is a bonus nice to sit out with a drink in the sun. We only stayed 4 nights visiting family but love Roscoe village and would definitely stay again in Dennis’s apartment.

We stayed for a week in Chicago and Cathy's apartment was perfect for us. The apartment was clean and comfortable, just as described, with all the facilities we needed. Great location, close to two stations, shops (including a great bagel shop and an ice cream shop), plus a short walk to plenty of restaurants. We would definitely stay again.

Lesley's place was even better than I had pictured: A cosy (yet spacious) apartment, that was clean and comfortable to stay in. It was also really well located (there's a bus stop right outside the apartment that can take you to downtown), and the neighbourhood itself was safe. Lesley herself is incredibly sweet, generous, and accommodating. I'm very glad I chose to stay there for 10 days in Chicago.

We had an amazing time on our Chicago trip & this Airbnb was perfect for our needs. The location was excellent for daytime activities and we really loved relaxing back “home”.

Friendly, communicative host. Great location. Will be back.

Steve and Long are amazing and friendly hosts, eager to accommodate their guests. They live in a beautiful neighborhood just around the corner from Aragon Ballroom. Their house is older but well kept. Not a ton of natural light, and the sides of the walls are slanted in so watch your head. The neighborhood is very quiet, which is nice given the typical noise pollution of Chicago neighborhoods. The bed is super comfortable and we kept the room cold all night. We could not ask for a better location or sweeter hosts. We loved our stay with them and look forward to booking there again soon!

We had a great long weekend stay in Chicago and the unit was perfect for our needs. Located on a quiet residential street and a short walk to L station Brown Line and also easily walkable to Wrigleyville and other nearby dining and shopping. The apartment was nicely furnished, very clean and had thoughtful amenities (snacks, drinks, extra towels). We had no issues during our stay, but John was proactive to occasionally check on our status and was available if needed. We would gladly stay here again on future visits to Chicago.

We enjoyed our stay at Mark's studio in Logan Square. It is about 10mins walk from the CTA station and the neighborhood is very walkable. We were able to drop off our bags a little earlier which was helpful, and Mark was very responsive. Will recommmend!

Rob’s place was great. Easy to find/get into, and very comfortable. Lots of thoughtful details included - loved the complimentary ear plus 😅 yes, the street is lively and therefore a little loud, but also my husband snores. Would definitely book again!

This place ticked off all my boxes for a great Airbnb. The space was clean, well decorated and had all amenities I needed. A big bonus was how quiet the neighborhood was and its easy access to the Blue Line train. The king-sized bed was the best for a good night's sleep and super comfortable. I would, without a doubt, stay here again on another Chicago visit.

Perfect place for a weekend trip to Chicago. Centrally located to all the activities and you can walk everywhere. If that's not your thing, a quick cheap Lyft/Uber to downtown, Chinatown, etc is the best option. We didn't drive so we didn't need parking, but Bel left out parking passes. That was a nice touch. Cozy bed, spacious bathroom, and nice kitchen. If we didn't have dinner plans both nights we could have cooked a whole meal. No issue with feeling unsafe. Such a beautiful neighborhod. We will try to seek this property again next time we're in the area! Highly recommended.

PROS: - 1 min walk to the Blue Line - Surrounded by amazing food options for all hours of the day and night - Felt very secure with sturdy doors, deadbolts, a swing bar door guard, and bars over the windows - Such a comfy bed! - Great natural light throughout the apt all day - Loved the extra fan, robes, slippers, toiletries, sleep masks, etc. - The space felt homey, like somewhere people live rather than a hotel - The host was very responsive and kind - There was a lovely bottle of bubbly with a welcome to CHI note in the fridge! - Check in and check out were easy and quick POTENTIAL CONS (neither of these were cons for me personally, but I could see them being cons for other guests): - The music from Logan 11 and the train passing by did make the apt vibrate at times - You have to go up two flights of stairs to get to the apt, so carrying heavy luggage might be tough

The apartment is beautifully renovated with a huge shower, fully stocked kitchen, and comfortable furniture. Even the bathroom is well stocked with toiletries! It’s located in a perfect spot just off Michigan Ave and only a couple of blocks from the Loop, Starbucks Reserve Roastery, and shopping. Bus stops and trains are also close by making it easy to navigate and experience all the city has to offer. Music from the bar can be heard at low volume in the living room (nothing the TV doesn’t easily drown out) and is barely noticeable in the bedrooms. The Armenian restaurant on the first floor serves excellent shawarma, kebabs, and mezza and is a must try!!! Tatiana and Roupen are wonderful, highly responsive hosts who provided everything we needed. We’d definitely stay here again!

Staying at this Airbnb was wonderful and cozy! It was a perfect home base for exploring the city, and Paul was incredibly responsive and helpful.

Josh’s place was wonderful. It was very clean. Even though there are people above you we barely heard them. Having a Keurig with k cups to start your vacation was very nice.

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

This cozy place was perfect for my husband and I visiting and watching our son for the marathon. The views from the floor to ceiling windows were spectacular. The location was perfect for us and very walkable to West Loop shopping and dining. It had very simple decorations and was very clean. Also the bed was super comfortable. Definitely got good sleep there. Can’t say enough good things about this property!

We had a great time in Chicago at this apartment. It was wonderful to be able to see Lake Michigan from the balcony. Walkable to a lot of restaurants and the Lake and Pier. Seriously was great for our large family - would definitely stay here again.

This was the perfect place for our group. We were only in town for one event so we spent a lot of time at the bnb. There was always something to do and none of us ever felt bored. Excellent spot to relax and unwind All of us are definitely keeping this place in mind if we ever need another weekend away!

I absolutely loved staying at this property. Everything about the location and the property was more than we expected. I highly recommend this property to anyone looking to explore Chicago.

It was a great spot, great location! The rooftop pool and upstairs lounge area was amazing! Would highly recommend staying here if you’re visiting Chicago

Lovely spot in Ukrainian village. Highly responsive host, good amenities, great location for a Chicago trip.