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Frank Lloyd Wright’s Schwartz House in Two Rivers, WI
Photograph: Courtesy Airbnb

The 9 best historic Airbnbs near Chicago

Marvel at the architecture, old-school details and quirky charm of these historic homes on Airbnb

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Modern apartments aren't for everyone. Gray rugs, silver furnishings, matching furniture… It's nice, but not as nice as something with charm and character. Think apartments with antique vibes, vintage light fixtures, real fireplaces and maybe, just maybe, original stained-glass windows. Sound like a dream? Then consider one of these historic homes near Chicago for your next trip.

Whether you're looking for a smaller property on a budget or you want to go all out and splurge, this is the list for you. We can't forget that mainline Chicago is stunning and well worth a visit. But sometimes, it's good to have a change—a bit of peace and quiet. So read on for our top recommendations of historic Airbnbs near Chicago.

RECOMMENDED: The best boutique hotels in Chicago

Who makes the cut? While we might not stay in every Airbnb featured, we've based our list on top reviews, hosts and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines. 

Historic Airbnbs near Chicago

The Frank Lloyd Wright’s Schwartz House in Two Rivers, WI
Photograph: Courtesy Airbnb

1. The Frank Lloyd Wright’s Schwartz House in Two Rivers, WI

This home was actually originally designed by legendary architect Frank Lloyd Wright for a LIFE magazine feature in 1938. And now, it's available to rent on Airbnb. You might also recognize it from Netflix's The World's Most Amazing Vacation Rentals. Of the design, Lloyd Wright wrote: “American family life is unlike any other in the world and I think this plan recognizes it for pretty much what it is—a little private club—with special privacies, ultra conveniences and style all the while." So that's exactly what you can expect. It's a huge four-bedroom, with a fully equipped kitchen and wood finishes. What a mid-mod dream.  

Rooms? Four. Sleeps eight guests.
Mood? A slice of history. 
Location perks? Just off the shores of Lake Michigan in a little vacation town to explore.
Budget range? On the pricey side.

The charming farmhouse near Lake Michigan
Supplied by Airbnb

2. The charming farmhouse near Lake Michigan

This peaceful getaway with great 1930s charm is like something out of a magazine. It's perfect for a big family or a big friendship group, as it has five bedrooms, plus room to sleep more. You definitely won't struggle for space here. In the master bedroom, you'll find a heart-shaped jetted tub that you'll struggle to get out of. There is also a games room full of retro fun and Lewis Farm Market nearby. And it's not far from Lake Michigan, so there are limitless possibilities for day trips.

Rooms? Five. Sleeps ten guests.
Mood? Quaint country living.
Location perks? It's surrounded by four acres of cherry and apple orchards.
Budget range? Super affordable.

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The castle on Roanoke in Peoria, IL
Photo: Airbnb

3. The castle on Roanoke in Peoria, IL

Located in the Randolph-Roanoke Historic District of Peoria, this regal structure stands out among a sea of classic Victorians. The stone exterior and prominent turret give way to an updated interior with two bedrooms, two bathrooms and a fully equipped kitchen. Plus, it's usefully located only a short distance from some major attractions, including Peoria Civic Center, the riverfront and the warehouse district.

Rooms? Two. Sleeps six guests.
Mood? Queens and kings of the castle. 
Location perks? Located conveniently close to all Peoria has to offer if you fancy venturing out.
Budget range? Surprisingly cheap.

The wooden A-frame in Elkhart Lake, WI
Supplied by Airbnb

4. The wooden A-frame in Elkhart Lake, WI

Located about a mile from the village of Elkhart Lake, this wonderfully cozy cabin is in the perfect location for thrill-seekers. With Road America motorsport course and golf courses nearby, plus Greenbush Kettle Moraine trails for great hiking, mountain biking and cross-country skiing, there are endless things to do. As for the property, you'll find a thoughtfully designed A-frame ceiling and spiral staircase separating the upper and lower levels. There's unique architecture dotted around the whole property, a large fire pit area perfect for summer BBQs, and a wrap-around deck with hip patio furniture.

Rooms? Two. Sleeps five guests.
Mood? Rustic retreat.
Location perks? Perfect for adventurous folk looking for a weekend of exploring nature and eating al fresco.
Budget range? A great deal.

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The old family farm in Sturgeon Bay, WI
Photo: Airbnb

5. The old family farm in Sturgeon Bay, WI

This sprawling historic farm has been in the same family for generations—116 years, to be exact. Though it's been updated with central air conditioning and other modern conveniences, the home features original hardwood floors and decades of family art. The spacious property offers plenty of opportunities for outdoor fun, too. Visitors might enjoy hiking, birdwatching, biking, snowmobiling or roasting marshmallows at the fire pit.

Rooms? Four. Sleeps ten guests.
Mood? Family getaway. 
Location perks? Oh, just 100 acres of farm and woodland to explore. No biggie.
Budget range? Very affordable.

The Hamilton House in Whitewater, WI
Airbnb

6. The Hamilton House in Whitewater, WI

Built in the 1800s, Hamilton House is a stunning example of Italianate architecture, which was saved from demolition in the 1980s by the town's residents and businesses. It's now run by Gloria Marie, who rents out its eight bedrooms to those visiting historic Whitewater. Each room is sympathetically decorated in a Victorian style and breakfast is included. There are also local activities such as biking and hiking in the Kettle Moraine.

Rooms? One. Sleeps two guests.
Mood? Historic charm. 
Location perks? In the heart of downtown Whitewater.
Budget range? Spenny AF.

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The Victorian home in Watertown, WI
Airbnb Victorian house Watertown Wisconsin

7. The Victorian home in Watertown, WI

Calling all antique home lovers, this Airbnb with Victorian charm has your name written all over it. Nicknamed "Belle Maison", meaning beautiful house, it's newly restored, with two bedrooms and two bathrooms. And the best thing is that one bathroom has its original claw foot tub. You'd be just a block from Main Street, with plenty of shops and restaurants within walking distance. And when you want a bit of nature and scenic views, take a visit to the beautiful Rock River which is also nearby. 

Rooms? Two. Sleeps six guests.
Mood? Victorian delight.
Location perks? In the historic district of Watertown—time to get exploring.
Budget range? Surprisingly inexpensive.

The 1800s home on Indiana’s Historic National Road in Greenfield, IN
Photograph: Courtesy Airbnb

8. The 1800s home on Indiana’s Historic National Road in Greenfield, IN

This white-paneled house has a long history of hosting travelers, after all, it operated as a stagecoach during the 1800s. The renovated interior features a few unique architectural elements, including a sliding barn door and intricate built-ins. It’s pet-friendly too, so you can bring your bestie along. Be sure to check out the back building, which actually features an outdoor bar. We'll cheers to that!

Rooms? One. Sleeps one guest.
Mood? Blast from the past.
Location perks? Stay on Indiana's historic national road and come away with a story or three to tell.
Budget range? Cheap and cheerful.

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The old schoolhouse in Lena, IL
Photo: Airbnb

9. The old schoolhouse in Lena, IL

Kerlin Schoolhouse, a cute little cottage just a couple of hours' drive from central Chicago, was built in 1870 and sits just off the historic Stagecoach Trail that once connected Galena and the big city. This is proper rural, so be prepared to hunker down. Cornfields surround the property on all sides and there are no neighbors for half a mile. But there's plenty to occupy you onsite, including a smart TV, barbecue and fire pit. The inside is the very definition of cozy (it was once a one-room school after all), with warm wood-panelled walls, a wood-burning stove (though there is modern heating too), and a mezzanine level, where you'll find the bedroom.

Rooms? One. Sleeps three guests.
Mood? Old world charm.
Location perks? Two state parks within a ten-minute drive.
Budget range? Cheap.

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