Boutique Andersonville Stay in a Historic Prairie School Home

Maximaliste et Magnifique

3BD, 2BR | Vintage Vibe | Lake, Music, Eats

Step into vintage charm at Maison Winona, a 1908 Prairie School stunner in the heart of Andersonville, voted Best Neighborhood in the U.S. This spacious 2-bedroom, 3-bed apartment pairs boutique comfort with bold maximalist style and a whisper of ooh là là. Enjoy a private balcony, free street parking, and walkability to Lake Michigan, the Green Mill, the Aragon Ballroom, Chicago Magic Lounge and Clark Street’s top restaurants. Perfect for families & friends seeking a one-of-a-kind Chicago stay.

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

What this place offers

Common

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

Bathroom

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

Bedroom and laundry

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

What this place offers

Common

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

Bathroom

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

Bedroom and laundry

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

Entertainment

  • Sound system

Family

  • Board games

Heating and cooling

  • Ceiling fan

Home safety

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

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

  • Lake access
  • Laundromat nearby
  • Beach access

Outdoors

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

Parking and facilities

  • Free street parking
  • Paid parking off premises

Accessibility

Neighborhood

Bienvenue à notre quartier — where things get delightfully EXTRA. Perched at the crossroads of Andersonville, Edgewater, and Uptown (a trifecta so charming it sounds made up), Maison Winona sits within one of the most richly diverse pockets in the nation — equal parts history, hedonism, and highballs. One moment you’re weighing the merits of Chimay vs. Delirium at Hopleaf, the next you’re debating jazz history with a saxophonist outside The Green Mill (they win). Need glitter? It’s on tap. Queer joy and craft cocktails flow from Marty’s to Meeting House, Nobody’s Darling to Farraguts — with go-go boys at Atmosphere and conversation that sparkles brighter than the disco ball. Need a moment? Lake Michigan is just 12 minutes east — bring a baguette, some aged brie, and your best existential crisis. Public transit? Mais oui. The Red Line whooshes you to Wrigley, the Loop, and Chinatown faster than you can say The Devil in the White City. Ready for dinner? You’re spoiled for choice — Korean fried chicken, Roman pastas, Southern biscuits, Taiwanese noodles, and over 20 James Beard and Michelin Bib honorees. It’s a global tasting tour within a half-mile radius. Need groceries? You’re surrounded. Specialty shops, mom-and-pops, and more tinned fish than you can responsibly consume. This neighborhood plates up every craving — with a side of people-watching that’s practically performance art. In short: if Wes Anderson moved to Paris, but it was Chicago, and everyone was just a little bit weirder (in a good way)? That’s the neighborhood. 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 📍 PRIME LOCATION - 9 min walk to Clark St (Over 80 Restaurants, Cafes, Shops) - 6 min walk to Redline Argyle Station/SunWah BBQ/Yoo Yee/Fat Miilk - 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 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. 🎓 Nearby Universities - Loyola: 7 min drive - Northwestern: 21 min drive - DePaul: 16 min drive 🚗 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 – CTA Bus 10-20 min wait. – Divvy bike rental station 3 min walk. 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.

Check availability

Reviews

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.
Patrick
July 2025 · Airbnb
Absolutely beautiful, well-stocked space, with amazing attention to detail. Do note, the owners who love downstairs do pay very careful attention to their doorbell cameras or something and messaged me at 1 AM politely requesting an immediate explanation because I had a single woman over for dinner and she was still in the apartment. They are within their rights on that, so it's still 5 stars from me, but this is atypical for AirBnBa, so just warning that you do need to register each and every guest in this spot or expect issues.
Amber
July 2025 · Airbnb
We loved our stay here and even my husband was saying it was the best Airbnb we have stayed at, he’s the picky one! It was beautiful, super clean, had everything you could need and then so much more! I would highly recommend this place!

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.