Get us in your inbox

Third Coast Cottage Airbnb
Photograph: Courtesy AirbnbThird Coast Cottage

The 10 most romantic Airbnbs near Chicago

Plan a romantic weekend away with these swoon-worthy properties

Written by
Morgan Olsen
Danielle Goldstein
Alex Floyd-Douglass

Sometimes sparking romance is as simple as changing your scenery – especially when Valentine's Day is around the corner. Get out of the apartment and hit the road for an intimate weekend away near Chicago. These romantic Airbnbs will take care of everything else, with amenities like hot tubs, fireplaces, and luxurious beds you'll be hard-pushed to get out of. There's something for every couple, too, whether your idea of romance is rustic and remote or sleek and in the center of it all. Browse the most romantic Airbnb properties in the Midwest and request that time off work – it's time to get away.

RECOMMENDED: The best secluded Airbnbs near Chicago

This article includes affiliate links. These links have no influence on our editorial content. For more information, click here.

Romantic Airbnb rentals near Chicago

The urban sanctuary in Kilbourn Park, Chicago
Photograph: Courtesy Airbnb

1. The urban sanctuary in Kilbourn Park, Chicago

As soon as you walk into this handsome studio apartment, the first thing you'll spot is the big canopy bed – it beckons with its white fluffy linens. A small kitchen has everything you need to prepare a quick bite and the bathroom is spa-like. Fun touches – like a wicker swing chair that hangs from the ceiling – make it feel like a great place to hole up.

The modern farmhouse in Kansas City, KS
Photograph: Courtesy Airbnb

2. The modern farmhouse in Kansas City, KS

There's a lot to love about this sweet and spacious 1930s bungalow, like the turquoise kitchen, the modern soaking tub, and the date-night–ready dining room. The hosts go above and beyond to make sure guests feel cared for, so expect a pile of chopped wood for the outdoor fire pit as well as lavender-scented pillows to lay your head on at night.

The glass cabin in South Bloomingville, OH
Photograph: Courtesy Airbnb

3. The glass cabin in South Bloomingville, OH

We can almost guarantee that you've never stayed in a place quite like this midcentury modern cabin that's perched on the edge of a 50-foot cavern. The floor-to-ceiling windows allow for jaw-dropping views of the surrounding forest and the sleek amenities make the stay feel luxe. Head outside to enjoy several patios, a massive hot tub, and an outdoor fireplace – all the trappings you need to set the mood. Come daytime, it's off to Hocking Hills State Park, where you'll find hiking paths and scenic views galore.

The secluded cottage in Miller Beach, IN
Photograph: Courtesy Airbnb

4. The secluded cottage in Miller Beach, IN

Hot tub? Check. Fire pit? Check. Proximity to a National Park? Check. This renovated 1920s cottage is a stone's throw from the Indiana Dunes National Park and offers plenty of romantic amenities for homebodies, too. Plus, the entire property is surrounded by a fence for maximum privacy while you soak in the six-person jacuzzi or enjoy dinner under the stars.

The tiny house by Off Grid Inn in Fall Creek, WI
Photo: Airbnb

5. The tiny house by Off Grid Inn in Fall Creek, WI

Become one with the woods when you book a retreat at this truly unique tiny house that's nestled deep in the Wisconsin wilderness. The minimalist and chic cabin is ideal for couples or solo travelers who are craving some serious time away (complete with spotty cell service). In addition to a queen-size bed, the cabin also features a small kitchenette and a shower room. Come summer, guests will enjoy panoramic views of thick green forest; in the winter, the cabin becomes your own private snow globe.

The restored cabin in Normal, IL
Photograph: Airbnb

6. The restored cabin in Normal, IL

If you don't mind getting a little rustic, this restored 1865 cabin is a charming landing pad for a weekend away. Nestled on a working farm, the one-bedroom abode looks out over miles of picturesque countryside. There's even a small no-frills kitchen and an outdoor fire pit for cooking a romantic meal together. But be sure to pack some layers and prepare to cuddle – the walls don't have drywall or insulation.

The Plāhaus in Nashville, IN
Photograph: Courtesy Airbnb

7. The Plāhaus in Nashville, IN

Nestled in the woods of Brown County, Indiana, this wonderfully modern abode serves log cabin vibes without the kitschy decor. Whether you want to hole up and watch old movies or disconnect over some classic board games, Plāhaus has it all. But we imagine you'll spend most of your stay on the elevated patio out back, which affords guests stellar views of the surrounding nature – a focal point no matter the season.

The designer apartment in Lincoln Square, Chicago
Photograph: Courtesy Airbnb

8. The designer apartment in Lincoln Square, Chicago

If you need to get out of your apartment for a few nights but don't want to splurge on a pricey hotel, consider this one-bed in Lincoln Square. Conveniently located above Dollop Coffee, this tasteful hideout has everything you could need: a full kitchen with a table for four, a nicely decorated living room, a modern bathroom, and an inviting bedroom.

The dreamy tiny house cottage in Nashville, TN
Photograph: Courtesy Airbnb

9. The dreamy tiny house cottage in Nashville, TN

Up for a long drive? Tennessee's most wish-listed home is worth the trip. This fairytale-esque tiny cottage is filled with vintage furniture and playful touches. Spend the day reading books on the day bed, admiring the backyard, or sipping beers on the patio. When night falls, there's a lofted bed that's tucked above the kitchen.

The star-gazer sky cabin in Upsala, MN
Photograph: Courtesy Airbnb

10. The star-gazer sky cabin in Upsala, MN

Is there anything more romantic than gazing up at the galaxy together? This stilted treehouse is surrounded by woods and countryside, making it easy to spot stars in the night sky. Adventurous couples will love the fact that it's located near the 27-mile Soo Line Trail, where visitors are welcome to walk and bike in the summer and snowmobile in the winter.

Looking to go off the grid for the weekend?


    More on Airbnb

      You may also like
      You may also like

      The best things in life are free.

      Get our free newsletter – it’s great.

      Loading animation
      Déjà vu! We already have this email. Try another?

      🙌 Awesome, you're subscribed!

      Thanks for subscribing! Look out for your first newsletter in your inbox soon!