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Boutique Andersonville Stay in a Historic Prairie School Home

Maximaliste et Magnifique

2 BR 3 BD | Historic Stay | Green Mill, Eat, Shop

Maison Winona is a 1908 Prairie School gem in Andersonville, named Best Neighborhood in the U.S. With a Walk Score of 95, this apartment offers easy access to vibrant dining, and cultural hotspots. Bold maximalist design, boutique comfort, and a private balcony await. Enjoy free street parking and walkability to Lake Michigan, the Green Mill, the Aragon Ballroom, Chicago Magic Lounge, and Clark Street’s best spots. A perfect retreat for design lovers seeking a unique Chicago experience.

Chicago, IL, United States
6 guests
2 bedrooms
1 bathroom

What this place offers

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • TV
  • Wifi

Bathroom

  • Bathtub
  • Body soap
  • Conditioner
  • Hot Water
  • Shampoo

Bedroom and laundry

  • Bed linens
  • Extra pillows and blankets
  • Hangers
  • Iron
  • Room-darkening shades
  • Clothing storage

What this place offers

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • TV
  • Wifi

Bathroom

  • Bathtub
  • Body soap
  • Conditioner
  • Hot Water
  • Shampoo

Bedroom and laundry

  • Bed linens
  • Extra pillows and blankets
  • Hangers
  • Iron
  • Room-darkening shades
  • Clothing storage

Entertainment

  • Sound system

Family

  • Board games

Heating and cooling

  • Ceiling fan

Home safety

  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector

Kitchen and dining

  • Baking sheet
  • Blender
  • Coffee
  • Coffee maker
  • Dining table
  • Dishwasher
  • Freezer
  • Hot water kettle
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Wine glasses

Location features

  • Beach access
  • Lake access
  • Laundromat nearby

Outdoors

  • Beach essentials Beach towels, umbrella, beach blanket, snorkeling gear
  • Patio or balcony

Parking and facilities

  • Free parking on premises
  • Paid parking off premises
  • Free street parking

Accessibility

Neighborhood

Bienvenue à notre quartier — where things get delightfully EXTRA. Andersonville— named the “second-coolest neighborhood in the world” by Time Out— Maison Winona sits within one of the most richly diverse pockets in the nation. With Clark Street as its beating heart, you’ll find a proud LGBTQIA+ spirit, acclaimed restaurants, and indie boutiques, and Lake Michigan a quick 12min walk away. Here for a show? You’re in the right place The Aragon Ballroom and Riviera Theatre are just a 7-minute walk from Maison Winona, hosting everyone from indie icons to disco legends. Prefer something with a little more brass and bourbon? The Green Mill swings seven nights a week — live jazz, strong cocktails, and serious Prohibition vibes (yes, Al Capone was a patron). Whether you're here for the headliner or just chasing a soundtrack for your evening, Uptown nightlife hits all the right notes — no rideshare required. Restaurants, restaurants, everywhere. Good luck picking just one! Sun Wah BBQ (5-min walk) is a James Beard Award–winning Chicago icon — their Beijing duck dinner is carved tableside and served with fanfare. Kiē Gol Lanee follows with bold Oaxacan flavors and a Michelin Bib Gourmand to prove it. Cariño, awarded a Michelin star in its first year, offers an exclusive late-night taco omakase that’s as intimate as it is unforgettable. Bar Roma serves Roman pastas with candlelit swagger, while Vincent gives Dutch comfort food a seasonal, modern twist. Little Bad Wolf delivers the burger that launched a thousand TikToks, and The Good Wolf features a lobster Reuben, a top-notch hot dog, and a classic Italian beef — all served in a speakeasy atmosphere that feels equal parts cozy and clandestine. Big Jones brings the biscuits (and the bourbon) to one of Chicago’s most celebrated Southern brunches. But the cravings don’t stop there. Uvae pairs oysters with an ever-changing wine list and a stellar happy hour. Tesfa brings Ethiopian heat and hospitality, Herb offers serene, elevated Thai, and Yoo Yee is the viral darling of your social feed. Birrieria Zaragoza’s goat birria? Worth the buzz — and then some. This isn’t your ordinary neighborhood. It’s a culinary crawl in a 15-minute walk radius. Is beer your love language? Welcome home. Hopleaf (9-min walk) isn't just any bar — it has been voted #1 beer bar in the world by Craft Beer & Brewing. With an extensive selection of Belgian brews and its famed moules frites, it's a pilgrimage site for those seeking the divine in hops. But the beer journey doesn't end there. Just beyond Maison Winona, a constellation of top-tier breweries awaits: Half Acre, Spiteful, Dovetail, Is/Was, and Urban Brew Labs each offer their own devotion to the craft. From crisp kölsches to barrel-aged wild ales, saisons to sours, this stretch of the North Side is essentially a self-guided tasting tour — bring your thirst and a designated walker. Need groceries? You’re surrounded. From the fresh herbs and produce at Tai Nam and Talard Thai to the spicy treasures of Middle Eastern Bakery and Old World Market, you're never more than a few minutes from something delicious. For specialty cheese and tinned fish (so much tinned fish), Andalle delivers. Park to Shop is your go-to for pan-Asian staples, while Edgewater Produce, Jewel, Mariano’s, Aldi, and Whole Foods cover the classics. Looking for a proper butcher? Gene’s Sausage Shop in Lincoln Square is worth the detour. Heading north? Devon Market and Morse Street Market bring global flair to your fridge. If you must cook, you’ll do so with more specialty shops, mom-and-pops, and culinary curiosities than you can shake a fennel frond at. This isn’t just a grocery run. It’s an international scavenger hunt with very chic tote bags. (P.S. Maison Winona has grocery bags for you — please don’t forget them. Stores are required to charge 15¢ a bag.) Here to connect with the vibrant LGBTQIA+ community? You’re spoiled for choice. From Marty’s to Meeting House & the SoFo Tap, Nobody’s Darling to Big Chicks & Farraguts — with patios, playlists, and people who get your pronouns right. And the celebration doesn’t stop there: Kathy Osterman Beach (aka Hollywood Beach/Ardmore Beach) brings a high-energy, pride-soaked vibe by the lake. The Leather Archives & Museum showcases rich queer history, and the Northalsted district buzzes with nightlife, Pride Fest, and Market Days — all just a quick 15-minute drive away. Need a break from the city’s buzz? Just walk east. The lake awaits. Foster Beach is your closest patch of sand — a quieter, more relaxed stretch perfect for a peaceful stroll, a solo sunbath, or a dip without the larger crowds Just a few blocks north, Hollywood Beach (aka Kathy Osterman Beach) delivers the energy — rainbow flags, curated playlists, and Aura, the beachfront restaurant slinging lobster nachos, fish tacos, and island-worthy cocktails. With table service in lounge chairs right in the sand, you’ll swear you’ve left the continental US entirely. Further south, Montrose Beach is where the action lives: volleyball courts, paddleboard and kayak rentals, and The Dock, a lively bar and grill with frozen drinks, live music, and sandy patio seating. On the quieter side of Montrose Harbor, you’ll find a peaceful bird sanctuary and one of the city’s best-kept secrets — panoramic views of the Loop skyline that hit especially hard at golden hour. Visiting Chicago in the summer and skipping the beach? Don’t do it. You’re missing one of the city’s most joyful, unexpected experiences — miles of freshwater shoreline, right at your feet. No need to bring beach gear in your luggage — Maison Winona has you covered. We provide beach towels, beach mats, beach bags, a wagon, backpack coolers, and a rolling cooler — so all you have to do is show up and choose your spot in the sun. Want to explore even more lakefront? Hop on the Red Line and head south to Oak Street Beach, Ohio Street Beach, or 31st Street Beach, or further north to Loyola Beach — all easily accessible and offering their own take on Chicago’s shoreline charm. Whether you’re chasing waves, tunes, skyline views, or just a bit of lakeside magic, the Foster Beach shore is just a 12 minute walk from Maison Winona — no car required. Public transit? Mais oui! The Red Line whooshes you to Wrigley, the Loop, Lollapalooza, Northerly Island, and Chinatown faster than you can say The Devil in the White City. Bienvenue à Maison Winona!

Guest Access

Guest Spaces: Private Second Floor Apartment Airbnb guests have full access to the entire private second-floor apartment—your chez-vous during your stay at Maison Winona. Thoughtfully designed within our 1908 Prairie School home, this space is both private and serene, offering vintage charm with modern comforts. It’s all yours for the duration of your reservation. Second Floor Balcony Enjoy exclusive access to the private second-floor balcony with sunrise & sunset views—a quiet, elevated escape nestled beneath the eaves. Whether you prefer your mornings with a café crème or your evenings with a clink of rosé, this private perch is yours alone. Shared Spaces: First Floor Balcony Lush with tropical hibiscus, cannas, and vibrant greenery, this front balcony is a shared space — and one of our favorite spots in the home. We hope you’ll treat yourself to a quiet café moment in the morning, a golden hour apéro as the sun begins to set, or a stylish pause while waiting for your ride-share (which usually arrives in 3–5 minutes, comme par magie). With its open-sky views and botanical beauty, it’s a little escape — no passport required. First Floor Front Entry Door & Hallway The main front entry and hallway are shared areas, part of the rhythm of life at Maison Winona. You may cross paths with us or our personal guests from time to time—day or night. We do our best to keep things quiet and courteous, and we’re grateful when guests do the same. Merci beaucoup! Back Entry Door & Stairwell To access the back door, Airbnb guests may stroll down the driveway and through the backyard—your own little detour en route to comfort. This entrance is available to you at any time. Just a heads-up: our two resident cats have claimed the stairwell as part of their personal promenade, so don’t be surprised if one of them offers a curious greeting along the way. They’re charming, opinionated, and consider themselves part of the welcome committee. Host’s Private Spaces Backyard The backyard is a private area reserved for the host and our personal guests. As you pass through to access the back entrance, you may spot us enjoying a meal, chatting with friends, or tinkering with the grill. We’d love to invite you to join us—but alas, City of Chicago regulations prohibit hosts from sharing food or alcohol with Airbnb guests (quel dommage!). We kindly ask for privacy during these moments and appreciate your understanding. The grill is for our personal use and not available to guests. Please note: the backyard is visible from the second bedroom closet, back stairwell, and the storage room off the kitchen. When in use, you may hear some gentle hums of life below—think of it as Maison Winona’s background soundtrack. Driveway The driveway is reserved for the host and our guests. You’re likely to see us coming and going at any time. We kindly ask that Airbnb guests do not park here—any vehicles found in the driveway may be towed, with fees billed to the guest. That being said, we welcome you to park briefly (20 min) in the driveway to unload your belongings upon arrival and load your belongings on departure. Merci beaucoup! Street parking is usually available nearby—please let us know if you’d like recommendations.

Good to know

🚗 PARKING - Free Street Parking 🧳LUGGAGE DROP-OFF - Free after 12 Noon on day of arrival. 📍 PRIME LOCATION (95 Walkability Score) - 9 min walk to Clark St The shop local capital of Chicago (Over 80 Restaurants, Cafes, Shops) - 6 min walk to Redline Argyle Station/SunWah BBQ/Yoo Yee/Fat Miilk, Patisserie P. - 12 min walk to Lake Michigan (Foster Beach) - 9 min walk to Green Mill/Riviera/Aragon Ballroom/Chicago Magic Lounge -15 min walk to Cariño. 2025 NYT 50 best Restaurants in US. 🛏️ BEDROOM 1 (Primary) - King bed - Hotel quality linens - Vintage chaise lounge - Walk-in closet - AC (Midea U 12K BTU smart inverter) - Ceiling fan - Full length mirror - Luggage rack 🛏️ 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 – Seats 6 (sofa, loveseat, vintage chairs) – Decorative (non-working) fireplace – 45" LG Smart TV – Hulu & Disney+ (No Ads) provided – Use your own login to access a variety of streaming apps – Samsung Bluetooth soundbar system – AC (Midea U 12K BTU smart inverter 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 🛁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 Titan ice packs PRIVATE COVERED 2ND FLOOR BALCONY – Seats 6 OPEN 1ST FLOOR BALCONY (SHARED) – Seats 5 📷 CAMERAS There are 8 exterior cameras: - 1 doorbell camera, and camera at the front door - 1 on the exterior first floor entry and hallway - 2 on the exterior second floor balcony - 1 on the exterior first floor balcony - 2 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. 🎓 Nearby Universities - Loyola: 7 min drive - Northwestern: 21 min drive - DePaul: 16 min drive 🚗 PARKING DETAILS: – Free street parking. Free street parking can easily be found on neighboring streets north of Foster on Magnolia, Wayne, and Lakewood. It is unlikely you will need to use paid parking but if you do try these parking apps: – Paid street parking via ParkChicago app – Paid nearby options via SpotHero app Both of these apps are useful if you are parking your car throughout Chicago. SpotHero specifically can save you a significant amount of money. On-site un-loading & unloading is available upon arrival and departure. TRANSPORTATION – Uber/Lyft: typically 3–5 min wait – CTA Red Line: every 3–9 min (day), 15–20 min (night); operates 24/7 – CTA Bus 10-20 min wait. – Divvy bike rental station 3 min walk. GETTING TO MAISON WINONA 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. ________________________________________ 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. ________________________________________ House Rules Agreement – Booking our property equals guest agreement to comply with House Rules and the rental agreement. – Violations may result in: – Notification to Airbnb and/or local authorities – Booking termination without refund – Guest liability for damages, fees, legal expenses ________________________________________ Optional Add-Ons – 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.

Other Details to Note

A rare architectural gem designed by Frederick Schock in 1908, this home was built for Lyman A. Budlong of the Budlong Pickle empire. Schock, a notable Chicago architect born to French immigrants and best known for four Victorian-style homes in the Austin neighborhood, was a contemporary of Louis Sullivan and Frank Lloyd Wright. Some historians claim that Wright copied Schock when he built his first residence in Oak Park in 1899. Scandalous? Peut-être. Delightfully plausible? Absolument! This greystone is one of Schock’s rare Prairie School designs, and we feel truly honored to steward and share it as Maison Winona. Our home is not a museum, but a lived-in love letter to design history. The interiors blend authentic Arts & Crafts elements like William Morris, Cole & Son, & House of Hackney wallpaper with bold nods to Art Nouveau, Art Deco, Victorian maximalism, and hints of mid-century and contemporary revivals of those styles. The vibe is infused with a touch of whimsy and a wink of kitsch, the kind that suggests we take beauty seriously, but not ourselves. We especially enjoy hosting fellow architecture and design enthusiasts—but truly, this home is for anyone who appreciates comfort, character, and a bit of story in their surroundings.

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Reviews

Kaitlin
October 2025 · Airbnb
This was undoubtedly one of the best AirBnB locations I’ve ever stayed at. It was SO beautiful and eclectic, not to mention incredibly clean and well-stocked. They’ve really thought of everything. The location was also amazing, within walking distance of so many neat shops and restaurants. Could not have been more pleased. Thank you for the warmth and hospitality!
Holly
September 2025 · Airbnb
We were completely blown away by this space! First, it is just a really cool and unique building and a place you’ll want to hang out in. Every detail and bit of decor is just so cool, and the balcony was so enjoyable for morning coffee on a sunny late summer weekend. The place was immaculately clean; we were all in awe how there wasn’t even a speck of dust anywhere! It was so comfortable from the beds to the hanging out spaces, we just didn’t want to leave! And the hosts are so considerate. Everything you could think of needing, the hosts already thought of and made available for you to feel at home and welcome. From brunch to beer to beach and everything in between, this is THE place to stay in Chicago! It made our weekend so special.
Alec
August 2025 · Airbnb
I can’t say enough great things about this Airbnb. The interior was absolutely stunning and you can tell the hosts put a lot of thought into it. I really appreciated all the little details. Johanna was always very responsive and provided lots of great recommendations. The location is super convenient as well. At the corner of Andersonville, Uptown, and Edgewater, there is a ton to do nearby. The Red Line is a 10-15 minute walk, and there are multiple bus lines very close as well. Highly recommend this place for someone wanting to experience what life in a Chicago neighborhood is like.
Johanna
August 2025 · Airbnb
Absolutely loved my stay here! The space is beautifully decorated with so much thought put into the design—it felt warm and inviting the moment I walked in. Super quiet and peaceful, which made it easy to relax. The home was stocked with literally everything you could need, which made the stay even more comfortable. Honestly not a single complaint—would happily stay again.
Antoinette
August 2025 · Airbnb
This home looks even better than the photos. I felt like I was staying at a friend’s home. Everything was wonderful. The couches and chairs and beds were all comfortable. The pillows, lighting, throw blankets were perfect. The bathroom and kitchen was stocked as if we were long awaited and cared for friends. It’s the best stocked air b n b I have ever stayed at. It’s a beautiful home AND the hosts are exceptionally thoughtful. I have to say I left wanting to be their friends!
Adam
July 2025 · Airbnb
This Chicago stay was perfect for our family of five. From the moment we arrived, it was clear that Johanna had thought of everything to make our trip seamless and enjoyable. The space was immaculately clean, beautifully decorated, and equipped with every amenity we could possibly need. What set this place apart were all the thoughtful touches - from having essentials like extra towels, toiletries, and special ice trays already stocked, to providing an extensive beach wagon with towels, mats and beach bags. The beds were comfortable, the WiFi was reliable, and there was plenty of space for our whole family to spread out and relax after busy days exploring the city. The location was very cool with easy access to the L train, and Johanna was responsive to our questions while still giving us complete privacy during our stay. If all Airbnbs were run with this level of care and detail, more people would choose them over hotels. We hope to stay here again!
Felix
July 2025 · Airbnb
Johanna is a truly wonderful hostess—gracious, thoughtful, and attentive to every detail. Her apartment is an absolute gem and one of the most best Airbnbs we've ever stayed in. It feels more like stepping into a beautifully curated home than a rental. Every corner is thoughtfully designed, with vintage touches, elegant furniture, and a charming collection of objets d’art that give the space real character and warmth. What really sets this Airbnb apart is how thoroughly it's equipped. Johanna has anticipated every possible need: there are not only kitchen essentials but also unexpected touches like rain ponchos, umbrellas, and an assortment of books and board games that were a big hit with our preteen kids. They especially loved exploring the apartment and discovering its cozy nooks and delightful details—it made our stay feel like a mini adventure. This is a place that welcomes you in and makes you feel instantly at home. We felt so comfortable and well cared for during our stay,
Susan
July 2025 · Airbnb
One of the most beautiful places I have stayed at. Truly, everything you would want and more. The hosts thought of every detail. They were so responsive and gave wonderful recommendations on places to eat at. The location is perfect for exploring a fun neighborhood. I will definitely stay there again. If I could give more stars I would.

Find us

Getting Around No car? No problem. You're just steps from the Red Line (Argyle station), which zips you downtown in about 30–40 minutes — straight to the Art Institute, Millennium Park, or that deep-dish you're pretending to try for the first time. Prefer pedal power? Divvy bikes are nearby, and Chicago’s lakefront trail offers breezy rides with skyline views. Lyfts and Ubers appear comme par magie, and street parking on Winona is free — though finding a spot can be a bit of a sport during peak hours (we’re in high demand, darling). For savvy parkers, nearby side streets like Lakewood, Wayne, and Magnolia are your hidden gems. Heading further afield? The Red Line connects you to nearly everything southbound — from Wrigley Field to Lollapalooza, to Chinatown, and all the eats, museums, and lakefront beaches in between. Maison Winona’s neighborhood trifecta — Andersonville, Edgewater, and Uptown — is best explored on foot. So grab a latte, hit the sidewalk, and let the day surprise you. (Hint: it usually ends with vintage finds and something très tasty.)

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Approximate location. Full address will be provided on booking.