Step into vintage charm at Maison Winona, a 1908 Prairie School stunner by Chicago architect Frederick Schock, in the heart of Andersonville. With interiors that whisper ooh là là, Maison Winona blends boutique comfort with a maximalist vibe. Enjoy a lush private balcony, and free street parking. A 10-min stroll brings you to Lake Michigan, the Green Mill, Chicago Magic Lounge, and Clark St’s top restaurants. Perfect for families, friends, and bon vivants seeking a one-of-a-kind Chicago stay.
PARKING - Free Street Parking
The space
PRIME LOCATION
- 6 min walk to Redline Argyle Station/SunWah BBQ/Yoo Yee
- 9 min walk to Clark St (Over 80 Restaurants, Cafes, Shops)
- 12 min walk to Lake Michigan (Foster Beach)
- 9 min walk to Green Mill/Riviera/Aragon Ballroom
Nearby Universities
- Loyola: 7 min drive
- Northwestern: 21 min drive
- DePaul: 16 min drive
BEDROOM 1 (Primary)
- King bed
- Hotel quality linens
- Vintage Chaise Lounge
- Walk-in closet
- AC
- Ceiling fan
- Full Length mirror
- Luggage rack
- Ensuite bath with walk-in shower & thermostatic system
- Spa tub inside walk-in shower
- Dedicated workspace with LED vanity mirror
BEDROOM 2
- Queen bed
- Hotel quality linens
- Blackout curtains
- Ceiling fan
- Closet
- Mirror
- Bedrooms 1 & 2 share a hallway
LIVING ROOM 2 (Flex Room)
- Day bed with queen size-trundle
-Balcony access
- When fully extended, the trundle fills most of the room — still walkable, just snug
-Low-profile bed sits directly at floor level — a slumber party feel with grown-up style
LIVING ROOM 1 & ENTERTAINMENT
– Seats 6 (sofa, loveseat, vintage chairs)
– Decorative (non-working) fireplace
– 65" LG Smart TV
– Hulu & Disney+ (No Ads) provided
– Use your own login to access a variety of streaming apps
– Samsung Bluetooth soundbar system
– AC
– 2 Gbps high-speed Wi-Fi
DINING ROOM
- Vintage Dining table seats 6
- Cocktail cart with shaker, tools & ice bucket
COFFEE & TEA READY
- Coffee bar with drip + French press
- Local Whole Bean Coffee, creamers, & sweeteners
- Pour-over tea kettle + tea selection
KITCHEN + BUTLER'S PANTRY
- Fully equipped Kitchen with quartz countertops
Other things to note
BATHROOM
– Clawfoot tub/shower combo (porcelain)
– Grab bars for entry/exit
– Tub is shorter than standard and requires high step-in
– Towels: 2 of each (bath, hand, washcloth) per guest
– 2 Conair InfinitePRO hair dryers
– Aveda Rosemary Mint: shampoo, conditioner, body wash, hand soap, lotion (starter supply – 12 oz each)
BEACH GEAR
– 6 beach towels, 3 queen-size mats, 6 beach bags
– 1 beach wagon
– 2 Titan backpack coolers, 1 Igloo wheeled cooler
– 6 reusable Titan ice packs
PRIVATE COVERED 2ND FLOOR BALCONY
– Seats 6
OPEN 1ST FLOOR BALCONY (SHARED)
– Seats 5
CAMERAS
There are 5 exterior cameras:
- Doorbell camera at the front door
- One on the second floor balcony
- One on the first floor balcony
- Two in the backyard
EARLY CHECK-IN OPTIONS
Early arrival is available for 75% of the average daily rate or your reservation if approved. Message us 24 hours in advance. Not available if another guest has booked or if maintenance is scheduled.
LATE CHECK-OUT
Late check-out is contingent on turnover needs. In the event that it is available, the rate is 75% of the average daily rate of your reservation. Please ask if interested.
PARKING DETAILS:
– Free street parking (limited 6 PM–8 AM)
– Paid street parking via ParkChicago app
– Paid nearby options via SpotHero app
– No on-site parking
Transportation
– Uber/Lyft: typically 3–5 min wait
– CTA Red Line: every 3–9 min (day), 15–20 min (night); operates 24/7
– Divvy bike rental station nearby
From O’Hare (ORD) (~1 hr 15 min):
– CTA Blue Line from terminal toward Forest Park
– Transfer to Red Line at Jackson (walk one block east)
– Red Line toward Howard
– Exit at Argyle
– Walk 2 min west on Argyle. Walk 3 min north on Broadway. Walk 1 min west on Winona. Maison Winona is directly West of the Dunkin Donuts.
From Midway (MDW) (~1 hr):
– CTA Orange Line toward Loop
– Transfer to Red Line at Roosevelt
– Red Line toward Howard
– Exit at Argyle
– Walk 2 min west on Argyle. Walk 3 min north on Broadway. Walk 1 min west on Winona. Maison Winona is directly West of the Dunkin Donuts.
Rental Agreement (Required)
– After booking, guests complete a rental agreement outlining house rules, occupancy limits, confirmation that unregistered overnight guests as well as unannounced guests are not permitted, check-in/out procedures, and Chicago’s Shared Housing Ordinance requirements.
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About the Space
Guest Private Spaces
– Entire second-floor apartment with covered balcony
Shared Spaces
– First-floor balcony
– Front entry & hallway – Shared; you may see us or our guests occasionally. We aim to be quiet and courteous—merci for doing the same!
– Back stairwell – Accessible via backyard. Our 2 resident cats may greet you—they're friendly and nosy.
Host’s Private Spaces
– Backyard – Private; not available to guests (City of Chicago prohibits food/alcohol sharing).
– Grill – Not for guest use.
– Visibility – Backyard may be seen from Bedroom 2, back stairwell, and storage room. Sound may carry lightly.
– Driveway — Guests may use the driveway for check-in and check-out only. It’s reserved for host use at all other times. Free street parking is available. Vehicles parked in the driveway during a stay risk being towed.
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House Rules Agreement
– Booking our property equals guest agreement to comply with House Rules and the rental agreement.
– Violations may result in:
– Notification to VRBO and/or local authorities
– Booking termination without refund
– Guest liability for damages, fees, legal expenses
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Optional Add-Ons
– Early Check-in / Late Arrival – 75% of average daily rate (when approved by host)
– Lost Item Return – $150/item for domestic shipping (restrictions apply – see House Rules)
– Cleaning during stay $275 when available. Must request 36 hours in advance. Payment in full required to reserve this service.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:As part of our booking process, guests must sign a short rental agreement after confirming their reservation..For everyone’s safety and enjoyment, reservations must be made by the actual guest(s) staying at the property. Third-party bookings are not accepted.,Quiet hours are from 10 PM to 8 AM, per city ordinance. Maison Winona is equipped with noise monitoring devices..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan main living space, soothing grays throughout, and an outdoor lounge space.
We strive to make your stay with us as great as possible and in order to ensure that we exceed your expectations we have some rules that will make sure your visit goes smoothly.
-Please do not use our towels to remove makeup or anything else that will stain them. If our towels are permanently stained we will charge a fee to replace them.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
A comfortable garden unit in a well cared for 3-flat, in a wonderful and safe neighborhood. Easy access to the lake front, dining and shopping. A great weekend getaway or a place to call home for a few months. Public transit is nearby, trains and express buses to downtown. Ride a bike home from downtown along the lakefront.
A neighborhood on Chicago’s north side, Andersonville is known for its Swedish roots, historic architecture, and bustling urban main street, Clark Street. When you arrive in Andersonville, you feel you have arrived someplace special.
Note: Being a garden unit, take note of the dropped heating pipes, particularly if you are taller than 6'2". Please see pics.
While our roots are Swedish, we are also recognized as the “shop local capital of Chicago,” supporting the largest network of local and independent businesses in the area.
Home to one of Chicago’s largest LGBTQ+ populations, Andersonville is a community full of pride and a commitment to equality.
* Parking is free on the street, no permits and easy
* Public transit is nearby
* Walk to neighborhood shops
* Little known secret: Take express bus to downtown shopping in 20 mins along lake shore drive, optionally ride bike home along the lakefront. The train is also an option.
My favorite places are the Hopleaf for a Belgian style brewpub atmosphere, very popular and Little Bad Wolf for dining. There is so much along the Clark St strip for shopping, don’t miss the Andersonville Galleria, a collection of shops in one venue. The brown elephant is another interesting thrift store for treasure hunts. Everything is close to your location. You’ll also want to go to the lakefront, just walk east down Berwyn, then at Sheridan look for a parkway to the north of Berwyn at Sheridan to get to the lakefront parks, great place for a bike ride. Ride north and it gets busier along the path. You’ll notice a Mariano’s grocery store (my favorite one) at Sheridan and Foster (you can get to the lake from Foster as well). There are two other grocery stores close by as well, depending on the direction you are headed. Oh, another great spot you’ll need to book in advance… Chicago Magic Lounge, a newly renovated flashback to a mid century atmosphere with reminiscent cocktails and a cozy setting for a magic show, a unique experience.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:Not responding to questions in a timely manner may result in cancellation of the booking..Respect the neighbors, particularly between the hours of 10pm - 8am,Do not dispose of anything in the toilet or hang anything on the pipes. This home is meant for work and rest - no other enterprises..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.
With a stay at The Guesthouse Hotel in Chicago (Uptown), you'll be within a 5-minute drive of Wrigley Field and Lake Michigan. This hotel is 5.9 mi (9.5 km) from Michigan Avenue and 6.7 mi (10.7 km) from United Center.
Enjoy recreation amenities such as a fitness center or take in the view from a rooftop terrace. Additional features at this hotel include complimentary wireless internet access, concierge services, and barbecue grills.
Featured amenities include a 24-hour business center, complimentary newspapers in the lobby, and a 24-hour front desk. Self parking (subject to charges) is available onsite.
Make yourself at home in one of the 25 air-conditioned rooms featuring kitchens with full-sized refrigerators/freezers and microwaves. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided on a limited basis.
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,About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 13-17.About customRules: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..NO Smoking or burning candles in or around the apartment building.,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.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
La Maison Verte is a Parisian-inspired 2nd floor walk up in a traditional Chicago 2 flat with vintage charm and modern amenities.
As you step inside you’ll be whisked away to a traditional Parisian flat with 9 foot ceilings, loads of natural light, custom wood panel molding, ceiling medalians, white marble, and brass finishes.
The French-inspired kitchen features blue cabinets and brand new Whirlpool appliances including gas range, ice maker, and stacked washer and dryer. Fully stocked with vintage glassware and dishes sourced from local antique shops.
Spacious 6 seat dining table with original built-in hutch which houses vintage barware and drink mixers.
The master bedroom features an 1880’s French walnut Queen bed with a full length gold mirror and kidney shaped desk for any work from home needs.
The home is a plant lovers dream with over 70 different plants sprinkled throughout. There is no better place for your morning coffee than the sun room/conservatory as you sit on a custom green velvet French Settee among the plants basking in the morning sun.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Our home is located in the quiet, but centrally located Buena Park neighborhood in an updated antique building. The location provides easy access to the Red and Purple train lines, as well as multiple bus lines to move you throughout the city. Nearby you will find many bars, restaurants, concert venues, and other great Chicago sites such as the Green Mill. Walking distance to Wrigley Field and Clark St. bars, Montrose Beach, Lakeview and Boystown bars.
The space
Roommate style 2 bedroom condo. Each room has an attached bathroom. The back room has access to the back entrance of the building. The condo comes with washer and dryer. All kitchen appliances are new. There is plenty of room to spread out and make yourself comfortable. Wifi is provided, as well as toiletries, linens & towels, hair dryer, ambient noise machine, umbrellas, iPhone charger with Bluetooth speaker, and other creature comforts. I will also provide you with the basics (folding chairs, beach towel, picnic and beach blanket, large hand cooler, speaker, etc.,) for an enjoyable time at the beach, lake, riverwalk, or park.
Room #1- The space is a large private room w/private entrance, bathroom, and fully furnished patio -all for your use only. This room is separated by two doors and a hallway from the rest of the condo, so you have full privacy, especially if you decide to use your private entrance. There is a queen bed that sleeps 2 and a twin folding bed (see last picture) that sleeps 1. The room also comes with a SAMSUNG 30" - 100" The Freestyle FHD HDR Smart Projector Home Theater. The bathroom has been recently renovated. This room has a kitchenette with a medium side fridge, microwave, Keuring coffee maker, air fryer, dishes, silverware, glassware, and a dinning room table for four.
Room #2- This room has its private bathroom. There is a queen bed that sleeps 2 and a twin folding bed (see last picture) that sleeps 1. Two large closets.
The train runs behind the building so expect occasional, but brief noise. No Parties are allowed- only the guests registered can be in the property unless you obtain special permission from me. Outdoor cameras monitor the back and front entrance.
Guest access
The whole condo
Registration number
R22000088593About pets:Pets allowed: dogs and cats (limit 1 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Welcome to our stunning retreat, perfect for families or friends seeking a stylish getaway. This beautifully designed unit boasts spacious living and dining areas, a playroom and a fully equipped kitchen, making it the ideal destination for relaxation and entertainment. The space is perfect for large groups and has everything you need to make your stay unforgettable.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Welcome to our cozy and stylish unit in the vibrant Andersonville neighborhood of Chicago! Nestled in the heart of this charming and lively community, your stay will be a perfect blend of comfort, convenience, and local charm.
Beyond the neighborhood, Chicago's renowned attractions are just a short distance away. Jump on the nearby CTA train or bus, and within minutes you can find yourself exploring the iconic architecture of the Loop or strolling along the scenic Lake Michigan shoreline!
The space:
This a large studio unit with anything you might needs for a comfortable stay. When you first walk in you are greeted by an expansive living room with a large sectional sofa. Near the living area is also a designated workspace with a large desk, mirror and cushioned lounge chair. Walking past the living area you will find 2 comfortable queen beds as well as a closet to hang your clothes. Opposite the sleeping area is a full bathroom with a tub. At the end of the unit you will find a full kitchen with a refrigerator, stove, dishwasher, microwave, kettle, toaster, and coffee machine. In this space is also a dining table that seats 4.
Guest access:
Guests are free to use any space within their unit as well as any of the outdoor spaces which include the front patio or lawn.
Other things to note:
This is an older building and there are tenants above the unit you will be staying in. The tenants are careful to avoid making any loud disturbing noise but if at any time it is too loud please message me and I will let them know immediately.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
This newly constructed studio offers a stylish, modern space just steps from Clark Street—home to some of the best restaurants, bars, and local shops in the city. With sleek finishes, smart design, and brand new furnishings, this space is perfect for solo travelers or couples looking for comfort and convenience. Whether you’re here to explore the city or just enjoy a weekend getaway, you’ll love being so close to the action while still having a quiet, cozy place to call home.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Welcome to one of the best home rentals in Chicago! Built in 2015, this 5 bedroom, 6 bathroom also boasts has an office, rec room/playroom and gym. Walkable to both Wrigleyville and Southport corridor, featuring a fully equipped kitchen, 2 fireplaces, 2 washer/dryers, wine fridge and radiant floors in basement and master bath. Outside has a spacious front yard, top floor roof deck, and an entertainers dream backyard including built in grill. Great for a weekend rental or longer stay.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.