There’s much more to be found in Illinois than Chicago, including rolling hills and a quiet way of life best enjoyed in a delightfully unique Airbnb.
Outside of Chicago, Illinois is probably best known for miles of farmland and Illinoisans’ profound love for “Da Bears.” But lesser-known to American travelers is the state’s exciting things to do outside of Chicago, including the charm of small-town Galena, the Shawnee National Forest, and the wine trails that cross the state.
Whether you’re planning a trip to The Windy City or looking to get away from civilization, these lovely Illinois Airbnbs are sure to make your trip one to remember.
Related Read: 12 Stunning Chicago Vacation Rentals for a Lively Windy City Stay
1. Logan Square Apartment
Why you should stay: A cozy top floor walk-up apartment with a magical balcony and a shared garden patio.
- Location: Chicago
- Sleeps: 5
- Minimum stay: 4 nights
- Rates start from: $169/night
Catching the attention of Buzzfeed, Chicago’s Logan Square apartment is a spacious two-bedroom apartment filled with fun and patterned decor. The hosts go above and beyond to provide helpful travel information for guests via their things to do bulletin board and custom map that shares their recommended neighborhood businesses.
The surrounding residential neighborhood of Logan Square is a historic Chicago district where visitors can experience the city like a local. This apartment is also near the Blue line that for convenient transport between the city and the O’hare International Airport.
Check AvailabilityRelated Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway
2. The Has Bin
Why you should stay: A rural farm-stay in a converted grain bin surrounded by country views.
- Location: Alvin
- Sleeps: 4
- Minimum stay: 2 nights
- Rates start from: $115/night
Escape to a simpler time at The Has Bin — a unique Illinois stay surrounded by the tranquil views of farm fields blowing in the breeze. Antique furniture and vintage accents set the scene in this renovated silo. The interior is divided into a ground level with a sofa bed and a lofted bedroom with an upper-level balcony overlooking the neighboring train tracks.
The property also features a fire pit, gas grill, and outdoor pavilion. This little piece of rural paradise is 40 minutes from the University of Illinois Champaign and 10 minutes from Danville.
Check AvailabilityRelated Read: 9 Delightful Weekend Road Trips From Columbus, Ohio
3. The Owl House
Why you should stay: A historic 1880 red-brick renovated warehouse near the Iowa border.
- Location: Galena
- Sleeps: 4
- Minimum stay: 2 nights
- Rates start from: $271/night
Historically once a warehouse, today The Owl House is a beautifully restored home with vintage yet modern touches that include owl-detailed windows, exposed brick interior walls, and contemporary furnishings. In the back, a screened-in porch looks onto the private yard with cafe-style seating.
This stylish airbnb is centrally located a block from Galena’s Main Street, where the city’s landmarks, shops, and restaurants are all within walking distance. Galena is a classically Midwestern small town that’s home to noteworthy buildings dating back to the 1800s, not to mention pretty vineyards.
Check AvailabilityRelated Read: 10 Exciting Weekend Road Trips From Indianapolis, Indiana
4. Emil Bach House
Why you should stay: An architectural wonder designed by the famous Frank Lloyd Wright with an exquisite Japanese tea room.
- Location: Chicago
- Sleeps: 6
- Minimum stay: 3 nights
- Rates start from: $386/night
As one of the world’s greatest architects, Frank Lloyd Wright found his first job drafting homes in Chicago, and the Emil Bach House is one of his works that still stands in the city today. Built in 1915, this historical home features natural prairie materials and forms that Wright was famous for, such as hardwood floors, exposed brick, and neutral tones.
This famous home also has unique amenities that include a sunny and modern four-seasons porch, an upper-level terrace, and a spacious garden and yard that’s a luxury in the city. Lake Michigan’s Jarvis Beach and Loyola Beach are conveniently a few blocks away.
Check AvailabilityFollow ‘em: @emilbachhouse
5. Havisham House
Why you should stay: A beautiful vintage home in southern Illinois surrounded by the Shawnee National Forest and Illinois wine country.
- Location: Alto Pass
- Sleeps: 6
- Minimum stay: 1 night
- Rates start from: $236/night
Tucked away on the southern border between Illinois and Missouri, the Havisham House is a spacious brick home in the heart of the Shawnee National Forest region that acts as a perfect event space or romantic getaway. Guests can enjoy local hiking trails through serene and quiet farmland and to the top of the Alto Pass Overlook.
The interior boasts a historic elegance married perfectly with today’s design aesthetics, which can be found in the charming wood crown molding, stained glass windows, brick accent walls, and delicate chandeliers.
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6. Rocky Hill Retreat
Why you should stay: A unique four-bedroom chalet on the outskirts of the city a short distance from Chestnut Mountain Resort.
- Location: Galena
- Sleeps: 10
- Minimum stay: 2 nights
- Rates start from: $364/night
The Rocky Hill Retreat is a family-friendly four-bedroom home surrounded by the quiet of a forested property conveniently located to the area’s top ski destination: Chestnut Mountain. Whether you’re a ski buff or just seeking a place to unwind, Rocky Hill offers guests a cozy place to stay in Illinois that’s thoughtfully decorated and sparkling clean.
Through the back sliding glass doors, a furnished patio complete with a dining table and a gas grill welcomes family cookouts. There’s also a fire pit for roasting marshmallows in the evenings.
Check AvailabilityFollow ‘em: @rockyhillretreat
7. Wicker Park Loft
Why you should stay: Sleep steps from Wicker Park in a trendy converted factory featuring brick walls, exposed ducts, and other industrial touches.
- Location: Chicago
- Sleeps: 2
- Minimum stay: 3 nights
- Rates start from: $150/night
For an ultimate Chicago experience, this Wicker Park loft places you right in the heart of one of the city’s hippest neighborhoods in close proximity to popular bars, restaurants, and terraces. This Airbnb Plus experience is housed in a historic brick building and melds together Chicago’s hyper-industrial vibe with Asian-inspired touches.
The space is an open floor plan and features a gourmet kitchen, eclectic design, and soaring ceilings. The bathroom has been outfitted with luxury touches, including a bidet, a Japanese soaking tub, and a rain shower.
Check AvailabilityRelated Read: 9 Delightful Weekend Road Trips From Columbus, Ohio
8. Enchanted Garden Treehouse
Why you should stay: A private room that comes packaged with a cool backyard treehouse and a hot tub.
- Location: Schaumburg
- Sleeps: 3
- Minimum stay: 1 night
- Rates start from: $239/night
This enchanted garden treehouse is a hidden gem in the suburbs of Chicago that offers a reprieve from the daily grind.
While technically this vacation rental is for a private room in the host’s primary residence, it comes with access to the property’s cedar treehouse set above a lush garden where a waterfall flows into a picturesque koi pond. The yard also has a cozy hammock, fire table, and grill for outdoor fun.
Check AvailabilityRelated Read: 9 Fabulously Unique Places to Stay in Illinois
9. H&H Farmhouse
Why you should stay: A spacious five-bedroom farmhouse near popular state parks such as Starved Rock and Matthiessen.
- Location: Magnolia
- Sleeps: 14
- Minimum stay: 2 night
- Rates start from: $250/night
H&H Farmhouse is a classically designed cabin with updated amenities that include a homey mudroom for storing outdoor gear, a lovely screened-in porch, and a relaxing hot tub.
The host has stocked this classy farmhouse with groups in mind and has countless board games, yard games, hammock chairs, and a circular bench fitted around the bonfire for your entertainment. There are also hiking trails that lead through peaceful woods to the Illinois River.
Check AvailabilityRelated Read: 10 Romantic Getaways Near Chicago, Illinois
10. Audrey’s Abode
Why you should stay: A quaint log cabin in a quiet rural community about 30 minutes from the state’s capital.
- Location: Jacksonville
- Sleeps: 8
- Minimum stay: 1 night
- Rates start from: $109/night
Audrey’s Abode is a charming little cottage that has been lovingly restored with reclaimed building materials from local farms and houses. It’s owned by superbly hospitable hosts who welcome furry friends and offer homemade coffee at check-in as thanks for your stay.
The nearest small town is only ten minutes away in case you’re in need of groceries, and Springfield is a pleasant 30-minute drive for those who wish to visit the capital. Guest Margie remarks, “Audrey’s Abode is absolutely adorable. It feels like you’ve gone back in time, yet still have modern-day conveniences.”
Check Availability11. The Barn
Why you should stay: Escape to the heart of Illinois wine country in an expansive luxury cabin.
- Location: Pomona
- Sleeps: 16
- Minimum stay: 2 nights
- Rates start from: $269/night
The Barn is a massive Illinois Airbnb in every way imaginable, with its 3100 square feet of space, five-bedrooms, and 70 acres of yard. It was once a barn that today features a sunny ground floor, an upper-level balcony, and a custom spiral staircase.
The property is an excellent option for large gatherings or events and has a playground to occupy the kids and a patio with outdoor seating and a fire pit for the adults. Popular attractions nearby include the Shawnee Wine Trail and the award-winning barbecue joint, 17th Street Barbecue.
Check Availability12. The Sedona
Why you should stay: Experience European charm in northern Illinois in a Spanish-style home with an enchanted Cantina, balcony, and five patios.
- Location: Rockford
- Sleeps: 8
- Minimum stay: 1 night
- Rates start from: $280/night
An unlikely sight in the Midwest, The Sedona is an intricately detailed Spanish-stye villa with a beautifully landscaped yard. As you step inside, tall ceilings, elegant furnishings, and vibrant pops of colors catch your eye.
This whimsical home also features a luxurious bathroom with a jetted tub and a walk-in shower. Other high-end amenities include a hot tub and various themed lounging spaces inside and out. The shops and eateries of Rockford are all only ten minutes away by car.
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Seen in: Illinois, Midwest, Where to Stay, Where to Stay in the Midwest
