Top 10 Exclusive Airbnbs in Illinois, USA For A Deluxe Experience

Getting the most expensive Airbnb in the world can be magical, but you have to pick the right one. So here is a list of the best 10 exclusive Airbnbs in Illinois USA that will give you a deluxe experience worthy of royalty.

Heading over to Millenium Park or Chicago Botanical Gardens can be exciting. Or dining at Everest or Shanghai Terrace. But all those experiences are more complete if you are staying in your home away from home. Staying at a hotel can be practical, but it remains impersonal and not so private. Booking an expensive Airbnb in Illinois can make a huge difference on your next trip there, so take a look at the hand-picked list of top 10 exclusive vacation rentals for a glorious experience.


Stunning Old Town Penthouse with Private Rooftop – About $1,199

Airbnb Illinois Stunning Old Town
Credit: Airbnb

A spacious penthouse situated in historic Old Town Chicago is one of the most expensive properties Airbnb in Illinois. A vintage French door will be separating you from a wonderful balcony. With 5 bedrooms and 4 bathrooms, this most exclusive Airbnb can receive over 16 guests. You will be amazed by 20-foot tall ceilings, and especially by the rooftop patio and jacuzzi tubs.

16+ guests | 5 bedrooms | 8 beds | 4 baths

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Resort-like estate over 7,000sf w/inground pool – About $950

Airbnb Illinois Resort like estate
Credit: Airbnb

In the world of luxury homes Airbnb this resort is close to O’Hare Airport, golfing courts, restaurants. Located in Riverwoods, this Airbnb in Illinois features 6 bedrooms and 5 and a half bathrooms, a large pool, basketball court, indoor gym. This is an ideal location for couples, families with children, but also business travelers.

14 guests | 6 bedrooms | 7 beds | 5.5 baths

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Laid-back luxe~minutes to McCormick Place! – About $1,000

Airbnb Illinois Laid back
Credit: Airbnb

One of the best vacation rentals in Chicago is this most expensive Airbnb home two minutes away from McCormick Place. The perfect Airbnb rental in Illinois is a modern 3000 square feet modern home that features 4 bedrooms and 3.5 bathrooms, kitchen, office, roof deck. The unique decor will leave you breathless, and the proximity to the new boat harbor and lakefront makes this home that much better.

8 guests | 4 bedrooms | 4 beds | 3.5 baths

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Wrigley Mansion – Sleeps 16+ – About $3,000

Airbnb Illinois Wrigleyville Mansion
Credit: Airbnb

For those of you who are searching for Airbnb exclusive homes to host a grand event, we have the ideal spot to do that. One of the best Airbnbs in Illinois sleeps between 16 and 24 people. Over 6,000 square feet of space inside this majestic mansion and 3,000 square feet of open air private land surrounding it. With so many interesting things to do in the house, you will scarcely find the time to explore the area.

16+ guests | 6 bedrooms | 12 beds | 5 baths

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Elle & Beck’s 2 story suite – About $1,350

Airbnb Illinois Elle Beck
Credit: Airbnb

Right in the center of Main Street in Galena, is a 5,000 square feet 2-story suit over 16 guests. This enormous Airbnb features 7 bedrooms and 4 bathrooms. It is located right across all the fun and must-see sites, restaurants, designer shops where you can spend your afternoons, but still, be only a couple of feet away from your luxurious loft.

16+ guests | 7 bedrooms | 8 beds | 4 baths

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Greenbriar Country Inn and Suites..Free Parking – About $1,200

Airbnb Illinois Greenbriar Country
Credit: Airbnb

With 12 bedrooms and 12 bathrooms, this exclusive Airbnb in Illinois offers its visitors a unique chance of enjoying the country charm. Located in the heart of Galena, this wonderful house has free, off-street parking, and it is only a short walk away from all historic sights, museums, but also restaurants and shops. Full maintenance and security is provided 24/7.

16+ guests | 12 bedrooms | 15 beds | 12 baths

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Gold Coast Designer Home Near The Magnificent Mile – About $1,500

Airbnb Illinois Gold Coast
Credit: Airbnb

The most exclusive Airbnb in the luxurious Gold Coast Area will be an ideal base for groups of 8 people. The sophisticated decor performed by a master interior designer will make your stay unforgettable. The downtown is only a few steps away from this incredible Airbnb, as well as many designer shops, mind-blowing restaurants, and North Avenue Beach.

8 guests | 4 bedrooms | 4 beds | 4.5 baths


Family Reunion Gem in Charming, Historic Riverside – About $995

Airbnb Illinois Family Reunion Gem
Credit: Airbnb

Victorian-era expensive Airbnb rental is perfect for family gatherings. Exclusive property boasts 5 bedrooms, a huge kitchen, dining and living room, as well as furnished front and back porch. Tucked away in a National Historic Landmark village near Chicago where over 16 guests can sleep. After a long day of exploring the area, you can spend your evenings relaxing in the hot tub.

16+ guests | 7 bedrooms | 24 beds | 3.5 baths


Designer Gold Coast Home | Steps from downtown – About $1,500

Airbnb Illinois Designer Gold Coast Home
Credit: Airbnb

A group of 7 can enjoy this 4-bedroom designer Gold Coast Airbnb in Illinois. Everything about this home exudes luxury and lavishness. The impressive master bedrooms, and crystal chandeliers, combined with high-ceilings and works of art on the walls will leave any guest completely satisfied after visiting one of the best places to stay in Chicago.

7 guests | 4 bedrooms | 4 beds | 4.5 baths


HUGE 8BR Wicker Park Complex – sleeps 18+ adults! – About $999

Airbnb Illinois HUGE 8BR Wicker
Credit: Airbnb

Modern and equipped with all the necessary house amenities but still with a lot of lavish spirits, this home will be a unique base for large groups of more than 18 people. $ kitchens, 4 living rooms, 4 bathrooms, and 8 bedrooms will provide enough space and comfort for each guest. You can stay together with all of your co-travelers but still have the privacy of traveling alone. Use the coziness of private deck space and lovely backyard to find a piece of mind after a long and tiresome day.

16+ guests | 8 bedrooms | 8 beds | 4 baths


Did You Like It?

It all comes down to you and your opinion of these extraordinary homes. If this article has been of assistance and you have found your home away from home, let us know. Tell us all about your trip, and what were your impressions of the vacation rental. We can’t wait to hear all about your exquisite journey!

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Kris Ryan Quirino
Kris Ryan Quirino

I'm a travel writer, researcher and engineer with two wonderful little kids. When I'm not taking care of my kids. I'm travelling and writing for various blogs online. My passion is renewable energy and I am currently completing a Masters part time in solar systems.

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