Apartment
Great Location-Beautiful Friendly Andersonville Neighborhood
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
3 bedrooms1 bathroomSleeps 4990 sq ft
Popular amenities
Explore the area

Chicago, IL
- Place, Riviera Theatre16 min walk
- Place, Aragon Ballroom18 min walk
- Place, Lincoln Park19 min walk
- Airport, Chicago, IL (ORD-O'Hare Intl.)22 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,
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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Amenities
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor Space
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10.0 out of 10, Exceptional, (11 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 13-17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you complete the following before checking out:
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
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.
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
We should mention
A car is not required for transportation to and from this property
About the neighborhood
Chicago
Located on a lake, this apartment is in Uptown, a neighborhood in Chicago. Chicago Theatre and Art Institute of Chicago are cultural highlights, and travelers 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. Motor boating, sailing, and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

Chicago, IL
What's nearby
- Swedish American Museum Center - 3 min walk - 0.3 km
- Riviera Theatre - 16 min walk - 1.4 km
- Aragon Ballroom - 18 min walk - 1.5 km
- Lincoln Park - 19 min walk - 1.6 km
- Loyola University Chicago - 4 min drive - 3.2 km
Getting around
Restaurants
- The SoFo Tap - 6 min walk
- Cafe Libra - 7 min walk
- Hopleaf - 3 min walk
- Starbucks - 6 min walk
- Taco Bell - 6 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Nov 28, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2025
10/10 Excellent
NICK D.
Dec 16, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
NICK D.
Stayed 3 nights in Dec 2025
10/10 Excellent
Lukas H.
Oct 17, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lukas H.
Stayed 3 nights in Oct 2025
10/10 Excellent
Kathy B.
Sep 14, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kathy B.
Stayed 3 nights in Sep 2025
10/10 Excellent
Kim M.
Oct 29, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kim M.
Stayed 5 nights in Oct 2025
10/10 Excellent
Clare D.
Jun 10, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home in a beautiful neighborhood!
Clare D.
Stayed 4 nights in Jun 2025
10/10 Excellent
Marcus V.
Jul 26, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Andersonville, Wrigley Field, & Chicago
Marcus V.
Stayed 7 nights in Jul 2025
10/10 Excellent
Kerry S.
Apr 7, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for a comfortable stay in a cute neighborhood.
Kerry S.
Stayed 3 nights in Apr 2025
10/10 Excellent
Brian W.
Sep 9, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Brian W.
Stayed 5 nights in Sep 2025
10/10 Excellent
thayna b.
May 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Would stay here again!
thayna b.
Stayed 4 nights in May 2023
10/10 Excellent
Alexandra D.
Jun 11, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay
Alexandra D.
Stayed 6 nights in May 2023
10/10 Excellent
Hope L.
Jul 19, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hope L.
Stayed 30 nights in Jun 2025
10/10 Excellent
Nathaniel H.
Oct 10, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Andersonville
Nathaniel H.
Stayed 3 nights in Oct 2024
10/10 Excellent
Jeremy J.
Apr 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Stay
Jeremy J.
Stayed 3 nights in Apr 2023
10/10 Excellent
Megan S.
Mar 25, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location, Location, Location!
Megan S.
Stayed 3 nights in Mar 2025
10/10 Excellent
Kyrstie N.
Jan 2, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Love Chicago!
Kyrstie N.
Stayed 7 nights in Dec 2023
10/10 Excellent
Garry M.
Aug 13, 2018
Clean, fun decor. Great neighborhood.
Garry M.
Stayed 2 nights in Jul 2018
10/10 Excellent
Renee B.
May 8, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
The perfect Andersonville apartment
Renee B.
Stayed 6 nights in May 2025
10/10 Excellent
Suzy F.
Jun 17, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family time in Chicago
Suzy F.
Stayed 3 nights in Jun 2024
10/10 Excellent
Gary A.
Oct 5, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay
Gary A.
Stayed 32 nights in Sep 2024
10/10 Excellent
Priscilla O.
Sep 26, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Priscilla O.
Stayed 6 nights in Sep 2025
10/10 Excellent
Nancy H.
Jan 26, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location in a beautiful apartment!
Nancy H.
Stayed 3 nights in Jan 2025
10/10 Excellent
Kim A.
Apr 4, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in Andersonville
Kim A.
Stayed 4 nights in Mar 2025
10/10 Excellent
Lorena M.
Mar 16, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and property
Lorena M.
Stayed 30 nights in Jan 2025
10/10 Excellent
Amy P.
Aug 3, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Property
Amy P.
Stayed 5 nights in Jul 2023
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.
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
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