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
Exceptional
3 bedrooms1 bathroomSleeps 492.0 sq m

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Outdoor space
  • Parking available
  • Free WiFi

Explore the area

Map
Chicago, IL
  • Aragon Ballroom
    ‪2 min drive‬
  • Loyola University Chicago
    ‪4 min drive‬
  • Wrigley Field
    ‪4 min drive‬
  • Chicago, IL (ORD-O'Hare Intl.)
    ‪36 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,

Property manager

Paul Harty
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Please do not wear shoes in the apartment
NO Smoking or burning candles
For easier check-in it is best to bring smaller luggage that can be easily carried up the stairs. Do not roll luggage across the stairs or floor

Important information

You need to know

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

We should mention

A car is not required for transport to and from this property

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. Lincoln Park Zoo and Field Museum of Natural History are not to be missed. 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

  • Riviera Theatre - 19 min walk - 1.7 km
  • Aragon Ballroom - 2 min drive - 1.8 km
  • Loyola University Chicago - 4 min drive - 3.3 km
  • Wrigley Field - 4 min drive - 3.6 km
  • Montrose Beach - 11 min drive - 3.1 km

Getting around

  • Chicago Ravenswood Station - 14 min walk
  • Argyle Station - 15 min walk
  • Chicago O'Hare International Airport (ORD) - 36 min drive

Restaurants

  • ‪SoFo Tap - ‬6 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪Replay Beer & Bourbon - ‬9 min walk
  • ‪Lady Gregory's - ‬6 min walk
  • ‪Atmosphere Andersonville - ‬9 min walk

Frequently asked questions

Is Great Location-Beautiful Friendly Andersonville Neighborhood pet-friendly?

No, pets are not allowed at this 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). Chicago Ravenswood Station is 14 minutes by foot and Argyle Station is 15 minutes.

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. 167 out of 179 reviews
Rating 8 - Good. 12 out of 179 reviews
Rating 6 - Okay. 0 out of 179 reviews
Rating 4 - Poor. 0 out of 179 reviews
Rating 2 - Terrible. 0 out of 179 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

10/10 Excellent

Kim A.

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

Great stay in Andersonville

Fantastic location and wonderful property. Walking distance to lots of restaurants, cute stores, the Swedish Museum, and the train to go downtown. We loved the charm of this older home. Everything was very clean, the beds were soft, and the shower great! I was a little concerned about on street parking but we were always able to find a spot near by.
Stayed 4 nights in Mar 2025

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

10/10 Excellent

Lorena M.

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

Great location and property

this house was perfect for my parents to stay over the winter months. Paul was a wonderful host, communicated regularly with them when needed. The place was extremely clean and just as described. There was plenty of spaces to be in inside of the house which was helpful in the cold winter days. Would stay again.
Stayed 30 nights in Jan 2025

10/10 Excellent

Nancy H.

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

Great location in a beautiful apartment!

Beautiful building! Comfy beds, well-stocked pantry with essentials. Great location, 2 blocks from CLark Street, but really quiet. Paul was great with communication.
Stayed 3 nights in Jan 2025

10/10 Excellent

andix3gmail

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

Nestled in neighborhood

Quaint and well appointed Victorian B and B. Tastefully decorated and only walking distance from nice shops restaurants and stores. Host quickly responds to questions. Very comfortable with all the comforts of home.
Stayed 3 nights in Jan 2025

10/10 Excellent

Sue F.

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

Family Winter Vacation

We came to Chicago for the Winter Classic. My grown kids and myself. To say the property was well maintained is an understatement. We loved the place. We would definitely recommend staying there and would love to stay there again. Our property owner Paul was wonderful so helpful we appreciated his hospitality if I could give 10 stars I would!!!
Stayed 4 nights in Dec 2024

10/10 Excellent

Karen O.

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

Holiday Stay

We stayed in this apartment over the Christmas holiday. It was very comfortable and conveniently located. We walked just about everywhere we went. Paul was a great host —helpful and available!
Stayed 5 nights in Dec 2024

10/10 Excellent

Ayden D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Oct 2024

10/10 Excellent

Verified traveller

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

Sister visit

My sister and I stayed in this lovely apartment for four days, and it was everything we needed it to be (and more, since we didn't take advantage of the well stocked kitchen; we were on vacation, after all). Lovely setting for a fall visit to Chicago. Everything was very comfortable and clean and the owner was very responsive to messages and even inquired if we were warm enough when the temperatures turned a little chilly one day. I hope I might get a chance to stay here again, perhaps for a friends' weekend.
Stayed 4 nights in Oct 2024

10/10 Excellent

Marisa F.

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

A Dream Accommodation!

This property is truly a beautiful and comfortable space with all of the amenities you could want. The host was proactively communicative and welcoming and the neighborhood gives off the same vibe. All the stars, highly recommend. Thank you again!
Stayed 3 nights in Oct 2024

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

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

10/10 Excellent

Family L.

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

Loved it.

Great apartment right by the village. It was even an easy walk home from Wrigley. Very comfortable, clean and nice decor.
Stayed 4 nights in Aug 2024

10/10 Excellent

Peter L.

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

Great Stay!

Nicely decorated, quiet and clean 2nd floor unit. Great communication with owner. Easy walk to Andersonville. Walkable to Lincoln Square, Wrigley, and lake. Highly recommended!
Stayed 7 nights in Aug 2024

10/10 Excellent

Stephen Y.

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

Chicago vacation

Paul's place was perfect for the four of us and came as advertised!! Close to all forms of public transit so it was easy to get to downtown, or just about anywhere else. If you don't want to go far, Andersonville has many dining options a close walk away.
Stayed 4 nights in Aug 2024

10/10 Excellent

Michael R.

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

10/10

Our host and the apartment were perfect. This is an experienced host… Exceptionally clean and well appointed place. We and our international guests were very comfortable and happy here.
Stayed 4 nights in Aug 2024

10/10 Excellent

lynn M.

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

Lovely Andersonville Apartment

We thoroughly enjoyed our stay in this lovely and very clean Andersonville Apartment. It's on a beautiful and quiet tree lined street, yet it's only a couple of blocks to all the fun of Clark Street. Paul was the perfect host and responded to any questions very quickly. I would highly recommend this property!
Stayed 4 nights in Jul 2024

10/10 Excellent

Senta C.

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

Quiet neighborhood in Chicago

Better than the pictures. Completely charming and very very quiet street. Parking is on the street but we didn’t have any problem finding a spot every day. Great communication with owner, quick response and a very nice person. Clean and well appointed. Would stay here again for sure and are sad to leave.
Stayed 4 nights in Jul 2024

10/10 Excellent

Rachel M.

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

Wonderful

This is great!
Stayed 3 nights in Jun 2024

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

8/10 Good

Karen F.

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

Perfect location

We attended my daughter's graduation at the United Center. This property was in a perfect location in Andersonville. So happy we also got to visit the town which was perfect. We enjoyed our stay
Stayed 6 nights in Jun 2024

10/10 Excellent

Korie S.

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

Lovely place to stay

We enjoyed our stay here very much. So much charm. The beds were comfortable, the neighborhood was quiet, and many stores and restaurants were in walking distance. We also walked to Wrigley Field which was an enjoyable walk down Clark St.
Stayed 4 nights in May 2024

10/10 Excellent

regina s.

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

great location and perfect condition

Went up for a quick Memorial Day weekend with family (18 years old daughter and 16 year old son). The place was absolutely charming and spotless and large enough that we didn't get in each other's way, even with only 1 bathroom. Paul, the owner was easy to communicate with and extremely accommodating. The neighborhood is safe and has lots of great restaurants within walking distance. Would absolutely stay here again.
Stayed 3 nights in May 2024

10/10 Excellent

Karen G.

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

Perfect

We were visiting for our daughter’s college graduation from Loyola. Really nice location. Many good restaurants to choose from within walking distance. Parking was very easy on the street. We always found a spot in front of the house. We appreciated all of the amenities provided: Kuerig with pods, plenty of high quality TP, high quality linens, comfortable beds, very quiet neighborhood, and clean updated furnishings. We noticed the attention to detail in the decorating with the Chicago theme. We’d stay here again for sure.
Stayed 3 nights in May 2024

About the host

Hosted by Paul Harty

Host profile image
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