This property was perfect for me and three teens heading to Lallapalooza. The layout of apt worked, especially liked spending time on the deck to start and end the day. Everything was convenient—shops, restaurants, bars. I liked the neighborhood so much I never made it downtown (though the nearby CTA brown line stop makes that easy). Do eat at Kitchn’s across the street. Bonus: Chicago Music Exchange is only 3 blocks away—if you are a guitar enthusiast plan to spend 3 or 4 hours there to play vintage and high-end instruments.

My husband and I had a wonderful three night stay!! The neighborhood is so welcoming and had everything we needed within a few minutes from the apartment. Jon, the owner, was easily accessible and had wonderful recommendations when we needed. A less than 10 minute walk to the train and we were in the city in no time. We definitely hope to visit this spot again!!

Jon's property is in a great location for walking to a Cubs game, shopping, and great food. The description is accurate! Jon was great about communication. Lovely place!

Very clean; pictures and reviews are very accurate. Place has a lot of character. I didn't love lugging the luggage up the steps and particularly the spiral staircase but once we were there it was great. Being over a restaurant/bar was a little noisy late at night but it really didn't disturb us. Highly recommend this place.

A wonderful stay in Roscoe Village. The location was absolutely perfect, and delightful to be in such a charming neighborhood away from the city. Loads of restaurants in walking distance. Only drawback were the stairs as we had far too many cases, but couldn’t be helped as we live internationally. We will definitely return!

We loved this place - great location - as described in the listing - easy access to everywhere we wanted to be in Chicago.

Clean, comfortable space above a sweet restaurant/wine bar. Had everything we needed. We enjoyed our comped bubbly in a patio cabana, and discounted bfast across the street. Had everything we needed in a cool, walkable area.

We really enjoyed our stay here. It was very comfortable and felt quite private for us even though we are in the city and above a venue. The location is great for restaurants, bars, sightseeing and visiting friends. The loft is well equipped and the rooftop deck makes it quite special. We will definitely stay here again when we are back in town.

Well equipped and clean. Access to the loft via circular staircase can be challenging if one has large luggage or a cooler.

If going to Chicago this is perfect place to stay. It’s in perfect location for anything you want to see and such a great friendly neighborhood. Jon was so great to work with and so easy to communicate with. Highly recommend to anyone.

Incredibly nice place to call home for 5 days/4 nights. Travelled with a friend for a couple of shows and ballgame in town. Very convenient location with numerous transport options nearby. We utilized busses, rail lines, Uber and bicycle rentals without any issues. 3 day "go anywhere" transit passes purchased at O'Hare was perfect. The penthouse was very roomy for 2 people, probably a bit big for our purposes, but felt great to be able to stretch out and relax. Super clean with every amenity you could imagine and super comfortable. Grocery items available from nearby stores if cooking. Lots of dining options within a few blocks and more than you'll need if you expand out a few more. The owner was available whenever needed, but we never once felt like we were staying in someone else's place (had privacy), which helped us feel totally relaxed. He even accommodated a special last minute request we had while he was in the middle of a busy time at his restaurant, which was above and beyond what was expected. Really can't say enough nice things about the place/location. Highly recommended!

The penthouse loft was as advertised: clean, well stocked, roomy, great location, and very comfortable. In addition, Jon, the owner was very accessible and helpful when I needed him. We will stay there again. Paul and Ellen

Walk to Wrigley location. Above a fantastic wine bar. Easy on street parking. Nice private terrace. Clean. Attentive ownership. Will definitely stay again when in town.

We love that we have family living in such a fun neighborhood in Chicago. Our rental was a perfect spot to enjoy all the local activities.

I must preface this by saying that I have never lived in the city - I grew up in the Chicago suburbs, so this was a great adventure for us. Roscoe Village is a darling neighborhood! You can enjoy walks along tree-lined streets, and there are boutiques and restaurants all up and down Roscoe. Family obligations prevented us from trying Volo, but we LOVED Kitchen on Roscoe (directly across the street from the apartment). We ate both a breakfast AND a lunch there and the food is TO DIE FOR. They have a nice outdoor patio in the back if the weather permits - You can't see that from the street so I mention it for those that like to dine outside like I do. Now on to the apartment - Can't say enough good things about it! It is comfy and beautifully decorated, and bedding and towels are all really nice quality. The bed and sofa are both very comfortable and there are skylights throughout that provide lots of natural lights - It is a HAPPY place! We enjoyed drinks on the rooftop patio one evening - very relaxing! It was also an unexpected treat to watch the Hawks at Riverview Tavern (although they didn't win, darn it) while we enjoyed Chicago pizza and craft beers. Wrigley Field is within walking distance and another plus - you can catch the "el" at Addison Station a few blocks away and take that into the city. We strongly recommend a visit to Millenium Park and Maggie Daley Park. We will most definitely be staying at Jon and Helene's on our next visit - I hope it is longer next time!

This was my first time booking a place on VRBO. If places turn out to be this nice I will be using this site a lot more. I was pleasantly surprised with the cleanliness, amenities and location. I wish I had my wife with me on this trip, it would have been a perfect spot for a romantic getaway! Directly below is VOLO restaurant!!! YUMMY! Also the outdoor patio was a perfect spot to enjoy the Chicago air! I would definitely RECOMMEND! Jon was a wonderful host and awesome guy if you get a chance to chat with him.

We stayed in the Penthouse and loved being above the Volo Wine bar where the staff were friendly and had great recommendations and ate twice across the street at Kitsch'n. John was very accommodating, was nice sitting out on the deck and there's lots of natural light coming in to provide an open roomy feel of comfort to the penthouse. I would definitely stay here again.

Overall, the place was great. Many amenities and well stocked kitchen and bathroom. No need to worry about bringing a hair dryer, shampoo, conditioner or body wash. Plenty of towels supplied. Kitchen even had some popcorn and air popper, coffee, tea. Nice, modern decor. Queen bed was comfortable for two. Unfortunately, the the pull out was not comfortable. Definitely needs a foam or temperpedic mattress pad to cushion the bars. The couch itself was deep enough after removing cushions to sleep on without pulling out the bed. Plenty of bedding was supplied which was needed since the slip cover looked like it needed a good washing. There was no window treatment on the patio doors so the street light was shining in. We just covered it with a throw blanket since there was a rod. On our day of departure we did find curtains on a hanger in the bedroom closet that I suspect were for the patio doors. We only had wifi for half of our stay. Jon came to reset it however neither my iPad or iPhone located it again. It was not that big of a deal to us since my daughter lives a block away. It might matter to others. I do think we will come back for another stay.

Jon was very accommodating. The place was comfy, clean and close to public transportation, plenty of yummy restaurants and parks for the kids. Would definitely return!!

We had a fantastic stay at this big, bright, adorable apartment in Roscoe Village! The location is amazing - right above Volo Wine Bar on Roscoe & N. Damen, on of the main intersections in the neighborhood. (Although despite the central location it was never loud in the apartment.) The balcony is large and overlooks the street - a GREAT place to hang out during the summer. Check in and out was super and easy and the owner, whom we happened to meet downstairs (he owns the wine bar) was very friendly and helpful. The place is clean and comfy, well stocked and decorated. The kitchen is small but well equipped for cooking (although I don't know why anyone would want to cook with all the great restaurants within walking distance). The Queen bed was quite comfortable and the pullout couch was fine for my son. This is a very family friendly, quiet but fun neighborhood. The public transportation is great, although we did rent a car. Street parking is easy to find within a block of the apartment. Whatever brings you to Chicago, you will feel like home at this apartment. I know we will be staying there again!

I write this only because I wish I had read a truthful review of this VRBO apartment. The owners are very nice ~ when I let them know there was an ant invasion they responded with action quickly. But......this is a very small, cleverly photographed (notice no bathroom photo.......) rather dumpy and dirty apartment in an area of town far from the top interesting spots for tourists to visit (aside from a great 30 minute walk to Wrigley Field) that was so far from the MOST EXCELLENT SPOT TO STAY EVER that I rather cringed coming in the door every time we did. 'We' being me and the just turned 50 year old I was treating to an ultimate adventure in Chicago. If this apartment were closer in price to a reasonable hotel room, I would have no issue - but we found the DIY decking an accident waiting to happen (with furniture SO rickeddy it begs to be replaced!), the steep spiral staircase up to the "penthouse" is a sadly overlooked detail for those staying with more than a backpack, the food across the street at Kitcsch'n was bad enough that we walked away at the first two bites, the list goes on and on (from 2 who have stayed at many VRBO apartments around the globe).....as 2 hardworking (overworked) women from Mpls who run a successful restaurant and constantly struggle to keep standards the highest, I encourage the owners to fix up the bathroom (!!!!!), and tend to some details in the apartment.

My friend and I were visiting Chicago for the first time and found this place to be exactly what we were looking for: relaxing, comfortable, clean and in a great location. The place is above a cute wine bar, and located on quiet street nearby lots of cafés and shops. It was only 20-30 min by train into the heart of downtown. Extra perks included the gift certificate for one of the local restaurants and wine bar located below. We thought that was a nice touch.

We had a great week in the penthouse loft. Loved the private deck in front especially on the warmer nights. Nice location situated between bars and restaurants. Didn't need to drive anywhere to have a great time. Jon the owner was very friendly and thoughtful. Apartment was well equipped with almost anything one would need. Would recommend this spot to everyone.