Apartment

Great Location-Beautiful Friendly Andersonville Neighborhood

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Winona Residence Since 1905
Winona St & Ashland Ave
Large Spacious Dining Room & Front Room. Table has been changed to seat 6
Large Spacious Dining Room & Front Room. Table has been changed to seat 6
Spacious Front Room with Cable TV and NetFlix

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Fenced yard
  • Free Wi-Fi

Explore the area

View in a map
Chicago, IL
  • Place, Riviera Theatre
    ‪18 min walk‬
  • Place, Aragon Ballroom
    ‪18 min walk‬
  • Place, Lincoln Park
    ‪19 min walk‬
  • 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,
Our prices include all fees. No hidden fees.

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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 travellers looking to shop may want to visit Michigan Avenue and Navy Pier. 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.
Map
Chicago, IL

What's 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
  • ‪Taco Bell - ‬6 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪Cafe Libra - ‬7 min walk
  • ‪Macaron Bar Andersonville - ‬4 min walk

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 190 out of 204 reviews
Rating 8 - Good. 14 out of 204 reviews
Rating 6 - Okay. 0 out of 204 reviews
Rating 4 - Poor. 0 out of 204 reviews
Rating 2 - Terrible. 0 out of 204 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Luz L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, spacious, cozy, great location.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 6 May 2026
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
Verified

10/10 Excellent

karen e.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great location! Loved Andersonville. Would definitely stay there again!
Stayed 7 nights in May 2026
Verified

10/10 Excellent

Alissa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was charming and gave the perfect old Chicago feel.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 21 Apr 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
Verified

8/10 Good

Gabriel B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and calm neighborhood withing great walking distance of any desirable location. The location itself is a well preserved slice of Chicago history.
Stayed 3 nights in Mar 2026
Response from VrboOwner on 20 Mar 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.
Verified

10/10 Excellent

Lesley M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location and very clean.
Stayed 4 nights in Nov 2025
Response from VrboOwner on 29 Nov 2025
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!
Verified

10/10 Excellent

Kathy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 3 nights in Mar 2026
Response from VrboOwner on 11 Mar 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
Verified

10/10 Excellent

Lukas H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a nice and clean space with 3 bedrooms and comfortable beds. It's a well decorated place in a beautiful area. We really enjoyed our stay.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 19 Oct 2025
Lukas, Thank you for the 5-Star Review! I'm so happy you enjoyed the apartment and the Andersonville neighborhood. Thank you again, Paul
Verified

10/10 Excellent

NICK D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 18 Dec 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
Verified

10/10 Excellent

Kathy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was very nice - just as described.We loved the location- quiet street near so many things
Stayed 3 nights in Sep 2025
Response from VrboOwner on 16 Sept 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.
Verified

10/10 Excellent

thayna b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Would stay here again!

Clean, great neighborhood, perfect for our family of four!
Stayed 4 nights in May 2023
Response from VrboOwner on 12 May 2023
Thayna, I'm so glad you enjoyed your stay. Thank you again, Paul
Verified

10/10 Excellent

Clare D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home in a beautiful neighborhood!

We had a great stay and loved walking around Andersonville. We will definitely be back!
Stayed 4 nights in Jun 2025
Response from VrboOwner on 11 Jun 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.
Verified

10/10 Excellent

Kim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Oct 2025
Response from VrboOwner on 29 Oct 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
Verified

10/10 Excellent

Alexandra D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

Host and neighborhood were wonderful!
Stayed 6 nights in May 2023
Response from VrboOwner on 14 Jun 2023
Alexandra, I'm so happy you enjoyed the apartment, the neighborhood and that the Cubs won a couple games while you were here. Thank you again, Paul
Verified

10/10 Excellent

Kerry S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for a comfortable stay in a cute neighborhood.

Clean, quiet and comfortable! Close to Andersonville shops and restaurants. Great location in city!
Stayed 3 nights in Apr 2025
Response from VrboOwner on 8 Apr 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.
Verified

10/10 Excellent

Marcus V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Andersonville, Wrigley Field, & Chicago

Great property, thoughtfully curated, and well cared for.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 28 Jul 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.
Verified

10/10 Excellent

Nathaniel H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Andersonville

Great place, friendly host. Definitely would stay again.
Stayed 3 nights in Oct 2024
Response from VrboOwner on 11 Oct 2024
Nate, I'm so happy that you and your family enjoyed the apartment and would like to come back to Winona in the future. Ty Paul
Verified

10/10 Excellent

Brian W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was ideal. Amazing!
Stayed 5 nights in Sep 2025
Response from VrboOwner on 16 Sept 2025
Brian, Thank you for the 5-Star Review! I'm glad you were happy with the apartment and the Andersonville Neighborhood.
Verified

10/10 Excellent

Jeremy J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Stay

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.
Stayed 3 nights in Apr 2023
Response from VrboOwner on 13 Apr 2023
Jeremy, I'm so glad you enjoyed your stay. thank you again, Paul
Verified

10/10 Excellent

Hope L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 30 nights in Jun 2025
Response from VrboOwner on 28 Jul 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.
Verified

10/10 Excellent

Kyrstie N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love Chicago!

Perfect location for us!
Stayed 7 nights in Dec 2023
Response from VrboOwner on 4 Jan 2024
Hi Kyrstie, I'm so happy you love Chicago! Ty, Paul
Verified

10/10 Excellent

Garry M.

Clean, fun decor. Great neighborhood.

I have stayed here before and will again. No surprises and easy access to restaurants and activities.
Stayed 2 nights in Jul 2018
Verified

10/10 Excellent

Megan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, Location, Location!

Beautifully appointed apartment in the perfect location for all Andersonville has to offer.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Suzy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family time in Chicago

We had a great time in this lovely apartment
Stayed 3 nights in Jun 2024
Response from VrboOwner on 17 Jun 2024
Hi Suzy, I'm glad you enjoyed the apartment. Thank you for the Nice Review! Paul
Verified

10/10 Excellent

Gary A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another wonderful stay

Our second, and most certainly not last, trip to the Winona property. Absolutely perfect stay again. See you next year.
Stayed 32 nights in Sep 2024
Response from VrboOwner on 6 Oct 2024
It's so nice to have repeat guests like Gary who return to the Winona Residence for a comfortable home away from home when visiting their families and the city. Ty
Verified

10/10 Excellent

Amy P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Property

We had a great stay at this property. It was clean, comfortable and well organized. We would highly recommend anyone choosing this apartment for your visit to the Chicago area.
Stayed 5 nights in Jul 2023
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