Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
Family fun awaits
Top rated for families.
Private garden
A rare find — relax in the peaceful, private garden space.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Near Aragon Ballroom
3 bedrooms1 bathroomSleeps 4
Popular amenities
Porch or veranda
Air-conditioning
Free Wi-Fi
Kitchen
Refrigerator
Onsite parking available
Explore the area
Chicago, IL
Riviera Theatre
Place, Riviera Theatre
18 min walk
Aragon Ballroom
Place, Aragon Ballroom
18 min walk
Lincoln Park
Place, Lincoln Park
19 min walk
Chicago, IL (ORD-O'Hare Intl.)
Airport, Chicago, IL (ORD-O'Hare Intl.)
30 min drive
Rooms & beds
3 bedrooms (sleeps 4)
Back bedroom
1 Queen Bed
Front bedroom
1 Double Bed
Middle bedroom
1 Queen Bed
1 bathroom
Bathroom 1
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden
About this property
Great Location-Beautiful Friendly Andersonville Neighborhood
City of Chicago Vacation LICENSE NO.: 2209341 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful tree-lined neighborhood of Andersonville.
Located in the FUN, EXCITING, ECLECTIC ANDERSONVILLE Neighborhood on the north side of Chicago less than 2-blocks west of Clark Street where you can find a wide array of Restaurants, Bars, Coffee Shops, Bakeries and Boutiques, etc.
This 2nd floor apartment has a private entrance and skylight above the front stair entry, with a balcony overlooking the tree lined street of Winona and in back a four season sun room overlooking the private back yard with a brick paver patio.
The Antique Furnishings complement the era of this turn of the century vintage home with some modern conveniences. You’ll love the hardwood floors, 9 foot ceilings, brick fireplace and exposed brick on the interior.
There are plenty of windows and beautiful warm colors throughout the home. There are 3-bedrooms, 1 bath, a front room leading to the balcony, a dining room, eat in kitchen with a pantry and a sunroom.
The apartment is located 2.99 Miles from Loyola University in Chicago and 5.99 miles from Northwestern University in Evanston. The apartment is located just 2-miles to Historic Wrigley Field and the Chicago Cubs.
Downtown Chicago and everything it has to offer is only a short distance when traveling by car you are just minutes to the beach’s of Lake Michigan and Historic Lake Shore Drive riding along the lakeshore looking toward the view of Down Town Chicago passing Belmont Harbor, Navy Pier, Oak Street Beach, Grant Park, The Magnificent Mile, Soldier Field and the Museums on Lake Michigan.
Downtown Chicago and everything it has to offer is only a short distance when traveling by public transportation. The Damen #50 bus and the Foster #92 bus are just 2-blocks from the apartment on Foster Avenue and Paulina. The Damen # 50 bus will take you to the Damen Avenue Brown-Line-L station. The Brown-Line-L will take you Downtown Chicago. The Brown-Line-L circles the Chicago Loop.
The Foster #92 bus will take you east to Broadway and you have your choice of the Argyle Red-Line-L station or the Berwyn Red-Line-L station. Both station stops will take you to the Chicago Loop. When you get to the city you may transfer to any one of the L-trains.
This location is very assessable by public transportation and by car. If you’re traveling from O’Hare Field, ride the Blue-Line-L train from the airport to the Jefferson Park stop and hop the Foster 92-bus to Paulina, just 2-blocks from the apartment. If you’re traveling from Midway Airport, ride the Orange-Line-L train from the airport to the Roosevelt Road stop and transfer to the Red-Line-L train and ride to the Berwyn stop and hop the Foster 92 bus to Paulina, again just 2-blocks to the apartment. Easy to find street parking on Winona Street. No Parking Permit Needed.
Keywords: Two Flat, Apartment, Beach, Wrigley Field, Loyola University, Northwestern University, Antiques, Bars, Restaurants, Shopping, Coffee Shops, Aragon Ballroom, Red-L-Station, Brown-Line-L station, Blue-Line-L-station, Metra Station, Bus Stop, Friendly Neighborhood, Lake Shore drive, Magnificent Mile, Millennium Park, Grant Park, Soldiers Field, US Cellular Park, Comiskey Park, Down Town Chicago, Chicago Loop, Hospital, theatres, loop, Navy Pier, O’Hare field, Midway airport, vacation rental, corporate rental, short term rental,
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The host requires you to complete the following before checking out:
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Hand wash any used dish's. You can leave them in the dish rack on the counter.
Bring the trash and recycle out. The containers are out back between the garages.
Place the towels in to the laundry basket across from the bathroom door. Hang any really wet towels over the side of the bath tub.
Failure to complete these may result in a negative review from the host.
Short Term Rentals Only 14 NIGHT MAXIMUM STAY
NO EXTENDED STAYS without owner Authorization
NO LARGE GATHERINGS in the apartment
Minimum Kid Age is 13
Shoes ARE NOT PERMITTED to be worn in the apartment Please REMOVE YOUR SHOES at the top of the front and back stairs before entering the apartment
LIMITED STORAGE. Best to bring smaller luggage for easier access and storage
NO SMOKING or burning candles in the apartment or on premises..
Important information
You need to know
Property # 302224vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Chicago
Located on a lake, this apartment is in Uptown, a neighbourhood in Chicago. Chicago Theatre and Art Institute of Chicago are cultural highlights, and some of the area's notable landmarks include Merchandise Mart and Cloud Gate. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center. Power boating, sailing and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Swedish American Museum Center - 3 min walk - 0.3 km
Andersonville Galleria - 5 min walk - 0.4 km
Riviera Theatre - 18 min walk - 1.5 km
Aragon Ballroom - 18 min walk - 1.5 km
Lincoln Park - 19 min walk - 1.6 km
Getting around
Chicago Ravenswood Station - 14 min walk
Argyle Station - 15 min walk
Chicago O'Hare International Airport (ORD) - 36 min drive
Restaurants
The SoFo Tap - 6 min walk
Replay Andersonville - 9 min walk
Starbucks - 6 min walk
Hopleaf - 3 min walk
Meeting House Tavern - 5 min walk
Frequently asked questions
Is Great Location-Beautiful Friendly Andersonville Neighborhood pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Great Location-Beautiful Friendly Andersonville Neighborhood?
As of 15 June 2026, prices found for a 1-night stay for 2 adults at Great Location-Beautiful Friendly Andersonville Neighborhood on 8 September 2026 start from NZ$504, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Great Location-Beautiful Friendly Andersonville Neighborhood?
On-site parking is available at the property.
What time is check-in at Great Location-Beautiful Friendly Andersonville Neighborhood?
Check-in begins at 4:00 PM.
What time is check-out at Great Location-Beautiful Friendly Andersonville Neighborhood?
Checkout is at 10:00 AM.
Where is Great Location-Beautiful Friendly Andersonville Neighborhood located?
Located in Uptown, this apartment building is 1 mi (1.6 km) from Riviera Theatre and within 3 miles (5 km) of Lake Michigan and Wrigley Field. Lincoln Park and Aragon Ballroom are also within 1 mile (2 km). Argyle Station is 15 minutes by foot and Berwyn Station is 16 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The space was clean and inviting with a fantastic location on a quiet street a stones throw from everything Andersonville has to offer. Would absolutely stay again!
Joseph T.
Stayed 5 nights in May 2026
Response from VrboOwner on 27 May 2026
Joseph, I'm so happy you enjoyed your stay. We pride ourselves in keeping the apartment clean and inviting.
This Vintage 2-flat is in such a nice quiet tree-lined neighborhood just a couple minute walk to Clark Street and downtown Andersonville. Ty, Paul
Luz, I'm so happy you found my apartment to be clean, spacious, cozy, and in a great location. I work hard between each guest stay to make sure all my guest feel the same way that you did when you walked into the apartment. You messaged me and said the place was beautiful. I really appreciated your positive response. Thank you. Paul
We had a great stay in this VRBO. The communication was great, never had an issue with our stay. Thanks so much for opening your home to us for our family trip for my son’s 16th birthday! It was very memorable!
Jen F.
Stayed 3 nights in Jun 2026
Response from VrboOwner on 14 June 2026
Jen, I'm so happy you had a Great and Memorable stay for your son's 16th Birthday. Ty, Paul
A beautiful home in a perfect neighborhood. Walking distance to public transportation and many shops and restaurants. Very clean and comfortable home. Plenty of amenities. Lots of room for a family of four.
jzdescoto
Stayed 8 nights in May 2026
Response from VrboOwner on 8 June 2026
I'm so happy you appreciated our clean spacious home in this beautiful Andersonville neighborhood, so close to public transportation and all the restaurants and shops downtown Andersonville has to offer.
The house was charming and gave the perfect old Chicago feel.
Alissa C.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 21 April 2026
Alissa, I'm so happy you appreciated our vintage Chicago 2-flat building. I hope for all my guests to have a good experience while staying in Chicago. I take a lot of pride in maintaining this home to give my guests a good comfortable place to vacation. Ty, Paul
Beautiful and calm neighborhood withing great walking distance of any desirable location. The location itself is a well preserved slice of Chicago history.
Gabriel B.
Stayed 3 nights in Mar 2026
Response from VrboOwner on 20 March 2026
I'm so happy you liked the neighborhood and the accommodations. This truly is a vintage Chicago 2-flat. I'm so proud of it.
Lesley, Thank you for appreciating our great location just 2-blocks from Clark Street and downtown Andersonville. We work hard on keeping the apartment clean and comfortable. Thank you for the 5-Star Review!
This is not the first time we stayed here.The owner is accessible, place is clean, parking available , great for 2-4 guests and reasonable cost for location.Hope to return
Kathy B.
Stayed 3 nights in Mar 2026
Response from VrboOwner on 11 March 2026
Kathy, It was nice to have you as our guest once again. I'm happy that you like the apartment and the neighborhood. I work hard at keeping the apartment clean and comfortable. We hope to see you again. Paul
Great, quiet apartment with three comfortable rooms. Great for a weekend, close to numerous restaurants on Clark within an easy walking distance. Parking was pretty crowded but we were able to find a spot on Winona Rd within a couple of blocks all weekend. Check-in was easy and exactly as described. We'll definitely consider this again next time we are in Chicago!
Jason N.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 28 April 2026
Jason, I'm so happy you liked the apartment and our location. Just a few minute walk to Clark Street, "Downtown Andersonville" with all the restaurants, bars, coffee shops, local shopping, CTA and Metra Public transportation. Normally, parking is pretty available during the day on Winona Street. (No Parking Permit Required) The street parking will start filling up later in the day. That's why I recommend parking your car on Winona Street and taking public transportation to the city. I'm glad your check-in was easy and I hope to have you as our guest when you come back to Chicago. Ty, Paul
The house was beautiful and spotless. Quiet location, short walk to Clark St with all the stores and restaurants. Would stay here again!!
Jane J.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 12 November 2025
Jane, I'm so happy you like the apartment and the Andersonville location so close to Clark Street with all the restaurants, coffee shops and shopping.
Thank you for the 5-Star Review.
It was very nice - just as described.We loved the location- quiet street near so many things
Kathy B.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 16 September 2025
Kathy, I'm so happy you liked apartment and the location on our beautiful quiet tree lined street in the Andersonville neighborhood. Our guest love our location because it is a couple minute walk to shopping, restaurants, bars, coffee shops, public transportation and so much more.
Beautiful and comfortable! My friends and I stayed here over the weekend and loved it. Convenient location within walking distance to come of the city’s best restaurants and bars. Clean, sunny and the beds were cozy! We will definitely consider staying here again.
NICK D.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 18 December 2025
Nick, I'm so happy you enjoyed your stay here at Winona. As you said, the neighborhood speaks for itself. Vintage tree-lined quiet neighborhood, just a a couple minute walk to Clark Street and downtown Andersonville with so many restaurants, bars, coffee shops, local shopping and so much more. We work hard at keeping the apartment clean and comfortable. The bedding is always washed and changed over after each and every guest have checked out. We would love to see you again in the future. Ty, Paul
We had a great stay and loved walking around Andersonville. We will definitely be back!
Clare D.
Stayed 4 nights in Jun 2025
Response from VrboOwner on 11 June 2025
Thank you for the Great Review. Andersonville is such a beautiful neighborhood on the north side of Chicago. My apartment is a few minute walk to Clark Street with so many restaurants, bars, coffee shops, public transportation and so much more.
Great for a comfortable stay in a cute neighborhood.
Clean, quiet and comfortable! Close to Andersonville shops and restaurants. Great location in city!
Kerry S.
Stayed 3 nights in Apr 2025
Response from VrboOwner on 8 April 2025
Kerry, Thank you for the Great Review! It was nice to have you and your family here for a Great Cubs weekend! I pride myself in keeping the apartment clean. I always follow up after the cleaning crew has cleaned the apartment to do a top cleaning and to make sure the apartment is ready for the next guests. You can't beat this location just on the edge of Clark Street and downtown Andersonville. And just 2-miles north of Wrigley Field.
This home is a fabulous place in an excellent neighborhood, close to restaurants and a quaint downtown area. The host is very responsive. Home is comfortable, clean, and spacious.
Kim M.
Stayed 5 nights in Oct 2025
Response from VrboOwner on 29 October 2025
Kim, I'm so happy you enjoyed the apartment and the Andersonville Neighborhood. I love my home, I work hard at making it a nice place for my guests to stay and it's only a couple minute walk to downtown Andersonville on Clark Street where you find restaurants, bars, coffee shops, local shopping and public transportation. Thank you for the 5-Star Review! Paul
Great property, thoughtfully curated, and well cared for.
Marcus V.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 28 July 2025
The apartment is in a Vintage Chicago 2-Flat Building. I take pride in taking care of the apartment and decorating it with Chicago Memorabilia. I want my guests to have a nice comfortable place to stay while they are in Chicago.
Wonderful experience and location. It was a great place to stay and return to Chicago with our family to share where we once lived. Thank you for the great accommodations.
Jeremy J.
Stayed 3 nights in Apr 2023
Response from VrboOwner on 13 April 2023
Jeremy,
I'm so glad you enjoyed your stay.
thank you again,
Paul
Beautiful, clean apartment in an excellent location to walk to all of the shops and restaurants in Andersonville. Really nice being able to get to the redline into the city easily or take a long walk or very quick drive to the lake beach.
Hope L.
Stayed 30 nights in Jun 2025
Response from VrboOwner on 28 July 2025
The apartment has so much to offer being a Vintage Chicago 2-Flat, in the Beautiful Andersonville Neighborhood, just minutes walk to Clark Street, restaurants, bars, coffee shops, local merchants and public transportation to downtown and Lake Michigan.
About the host
Hosted by Paul Harty
I am a 4th generation Chicagoan. My roots are very deep in the City of Chicago going back to my Great, Great Grandparents on both side of the family. I love Chicago and I currently live in the first floor apartment of The Winona Residence with my wife Cathy and our Irish Terrier Mickey. I am the Vice President of our Family owned heating and air conditioning company in the west suburb of Schaumburg Illinois. I have been in the heating and air conditioning business since 1976. I am a licensed electrician and I have a Managing Brokers Real Estate License.
Why they chose this property
The Winona Residence is located in the Chicago north side neighborhood of Andersonville. Andersonville is listed by Red Fin in 2015 as one of the Top Ten Neighborhoods in the USA. Listed at #7. The location is wonderfully located for easy access for all public transportation to downtown Chicago. The public transportation downtown Andersonville and Lake Michigan are within walking distance from the apartment.
What makes this property unique
This property is one of the First Vacation Rentals in then City of Chicago. Since 2010. This home is unique because of its vintage character from the early 1900’s and friendly neighborhood. Being on the second floor you get privacy from the tree lined street. You can admire the view while out on the front balcony or sit in the back sunroom looking out to the backyard. This location is very accessible to downtown Chicago and the walk is less than 2-blocks to the heart of downtown Andersonville.
Languages:
English
Premier Host
They consistently provide great experiences for their guests