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Cozy Chicago Airbnb Madison Street loft
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The coziest Airbnbs near Chicago

Whether you're looking to stay in Chicago or go for a weekend trip nearby, these Airbnbs offer an ultra-cozy escape

Written by
Emma Krupp
Contributors
Danielle Goldstein
,
Alex Floyd-Douglass
&
Camila Karalyte
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Sometimes you just have to pack your suitcase and head off on a break for a few days. You know, to 'find yourself' or at least avoid daily chores. So, why not take a day trip from Chicago and check out easy-to-reach Airbnbs just over the border in Wisconsin and Michigan, or even staycation closer to home? Both options provide ample possibilities for intimate evenings with loved ones or by yourself—no judgment.

Find your new favorite hideout and reconnect with yourself and nature at one of the most cozy Airbnbs near Chicago. The hard part will be choosing just one.

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Who makes the cut? While we might not stay in and review every Airbnb featured, we've based our list on our expert knowledge of the destination covered, editorial reviews, user reviews, hotel amenities and in-depth research 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.

The coziest Airbnbs near Chicago

The modern farmhouse cottage in southwest Michigan
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1. The modern farmhouse cottage in southwest Michigan

Looking to unplug in nature for a couple of days? Ditch the city and drive this sweet farmhouse cottage in Sawyer, Michigan. The 14-acre premises features pastures dotted with farm animals, woods and a barn. Inside the cottage, an elegant, modern kitchen—equipped with wooden butcher block counters and a bounty of cooking tools—offers an opportunity for whipping up a hot meal after a long day of hiking and exploring.

Rooms? One. Sleeps two.
Mood? Contemporary farmhouse vibes.
Location perks? Just under an hour and a half drive from downtown Chicago, with beaches, breweries and wineries nearby.
Budget range? Very affordable couple's getaway.

The whimsical cottage in Coloma
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2. The whimsical cottage in Coloma

Nothing is cozier than the soft glow of fairy lights twinkling around you. This whimsical cottage in the heart of Michigan's Great Lakes region is quaint, cute and steeped in history. The Airbnb sleeps up to four guests in twin trundle beds, but we think it's perfect on your own or with your other half. The vibes are enchanting and romantic, and it has everything you'll need for a cozy stay, including a fully-equipped kitchen, bathroom with shower, and an enclosed backyard with outdoor dining and a firepit. A small but homely space.

Rooms? One, but with room to sleep four.
Mood? Year-round wintery Christmas vibes.
Location perks? Easy access to the Southwest Michigan Wine Trail and the Fruit Belt.
Budget range? Affordable.

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The forest chalet on Lake Geneva
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3. The forest chalet on Lake Geneva

Enjoy the bustle of Lake Geneva at this peaceful cabin—billed as a "chalet" thanks to its ski resort vibes—tucked into the woods (even though it's only a two-minute drive to Williams Bay beach and other attractions). Cuddle up indoors under a furry blanket or endeavor to build a roaring fire in the pit in the backyard; either way, you're in for a restful weekend.

Rooms? Two. Sleeps eight.
Mood? Lumberjack, but make it fashion.
Location perks? With Geneva Lake and Williams Bay Beach so close, there is plenty of watersports fun to be had.
Budget range? Mid-range for two, budget for more.

The dreamy vacation home near Weko Beach
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4. The dreamy vacation home near Weko Beach

This stunning Airbnb in Stevensville has you—and 15 other guests—fully covered across five bedrooms and 14 beds. Unwind across the two acres of fenced land, featuring a fire pit, hot tub and wraparound porch for all of your outdoor endeavors. Cook up a storm in the open-plan kitchen before chilling by the indoor fireplace and giant flatscreen TV.

Rooms? Five. Sleeps 16+. Wowser.
Mood? Upmarket pine lodge.
Location perks? Stevensville is very much wine country. Look up the Grape & Grain tours, which offer complimentary transport.
Budget range? Eminently affordable if there are upwards of five/six guests.

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The cozy cottage in Southwest Michigan
Photograph: Courtesy Airbnb

5. The cozy cottage in Southwest Michigan

This southwest Michigan rental is the home of your cottagecore dreams, complete with eccentric decor, wood floors and a Jacuzzi in the master bathroom. Sit down with a good book in a rocking chair on the wraparound porch or cozy up beside the wood-burning stove. There are windows everywhere too, so it's wonderfully light-filled throughout.

Rooms? Two. Sleeps six.
Mood? Eclectic woodland hideout.
Location perks? Super close proximity to Lake Michigan—perfect for walks on the beach.
Budget range? Affordable for a couple.

The rustic lodge in North Chicago
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6. The rustic lodge in North Chicago

Who would have thought a garden unit could look so much like a Wisconsin lodge? This Rogers Park rental somehow manages to pull the effect off, utilizing soft carpet, fish-themed decor and wood-paneled walls to transport guests to the boreal environs of the Northwoods (minus the six-hour drive). Crack open a can of Schlitz in front of the fireplace and it'll be just like the real deal.

Rooms? One. Sleeps two.
Mood? Epitome of cozy.
Location perks? Walking distance to the red L-line, Loyola University is a few blocks away, and there are plenty of restaurants, coffeeshops and Lake Michigan beaches in the local area.
Budget range? Very affordable for two.

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The boho retreat in Racine
Photograph: Courtesy Airbnb

7. The boho retreat in Racine

Steal away from Chicago to this 1858 historic abode in Racine, Wisconsin, that's full of homey character. A couple of deep leather couches and some board games will make for lovely evenings spent by the hearth, while a two-story sunroom allows you to make the most out of winter light. Don't forget to read up on the history of the home before you leave!

Rooms? Three. Sleeps nine.
Mood? Classic meets contemporary in a historic building.
Location perks? Just five blocks away from the shores of Lake Michigan.
Budget range? Great value for money, even if you're traveling alone.

The bright loft on Madison Street
Photograph: Courtesy Airbnb

8. The bright loft on Madison Street

Hop on the Blue Line for a cozy escape to this luxe Forest Park loft located on the top floor of a renovated Masonic Temple. The apartment's exposed brick, leather, and burnished decor make for an almost speakeasy-type feel – but you'll also have access to a balcony if you'd like to take a break from the fireplace for crisp winter air and incredible views.

Rooms? Two. Sleeps four guests.
Mood? Minimalist design.
Location perks? Walking distance from the gorgeous Oak Park.
Budget range? Suuuuper affordable.

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The glamping cabin on Cold Spring Tree Farm
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9. The glamping cabin on Cold Spring Tree Farm

For a more rustic experience, head just over the border to this single-room cabin in Whitewater, Wisconsin, which is nestled on the premises of a 40-acre Christmas tree farm. You'll have to be comfortable with giving up certain conveniences (there's no running water, though fresh water in thermoses, an outhouse and an indoor bucket toilet are provided), but it's tough to beat the cabin's stone-walled charms: just imagine curling up in front of the toasty wood-burning stove after a long day of ice fishing.

Rooms? One. Sleeps four comfortably, more if you bring tents.
Mood? Back to basics.
Location perks? There's an indoor basketball court nearby, as well as wild swimming and fishing to be had in the pond (or skating in winter).
Budget range? Dirt cheap.

The country cabin near South Madison
Photograph: Courtesy Airbnb

10. The country cabin near South Madison

This farmhouse cabin just south of Madison is small and snug, making it a perfect getaway for a couple (and even a pet, as long as you ask ahead of time). Bring your binoculars to keep an eye out for birds – up to 46 species have been known to make an appearance on a good day. In the evening, soothe your tired muscles with a relaxing rest in the cabin's outdoor sauna.

Rooms? One. Sleeps two.
Mood? English country cottage.
Location perks? You can go cross-country skiing on the premises, they're so sprawling.
Budget range? Cheap for a couple.

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The log cabin in the woods in Geneva
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11. The log cabin in the woods in Geneva

Few styles of homes scream "cozy" more than a log cabin—and this rental, located in the popular weekend getaway of Geneva, is no exception. Settle in among the creekside spot in the Fox Valley and relax in front of the central fireplace, or bundle up for a spot of stargazing around the outdoor fire pit (all th better with a warm beverage in hand). The home has three bedrooms, two bathrooms and a laundry room in the basement.

Rooms? Three. Sleeps seven.
Mood? Rustic woodland living.
Location perks? Minutes from downtown Geneva, with its 8-square-mile lake, surrounded by a tree-lined Shore Path, and numerous unfussy eateries.
Budget range? Affordable if split between four, a bargain between six.

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