7 Mind-Blowing Airbnbs For The Ultimate Illinois Staycation

You could travel further afield, but these Illinois staycation options prove that some of the best places are on your own doorstep. Sometimes you don’t even need to leave your own state to have the most magical vacation experience.

These large Airbnb properties are the ideal place to escape with family, friends or even for a business retreat. With larger group bookings, Airbnbs often happen to work out as a more affordable option than hotels.

All you have to do now is round up a big group and start planning an Illinois staycation.

Best Airbnbs in Illinois for a Staycation

1. Resort-Like Estate – Riverwoods

This place is close to golfing, restaurants and O’Hare Airport, right off I-294, located in a breathtaking setting of Riverwoods .

You’ll love the house because of the resort-like feel in a private setting featuring extra-large pool, a basketball court, large dining room with custom table that sits 20+ people. The home is ideal for entertainment or corporate events or large family gatherings.

It sleeps 15 guests and comes in at just over $1000 a night.

2. Gigantic Sunlit Loft – Chicago

This gorgeous sun filled loft is as unique as they come. A former factory converted to a luxury home and quipped with a 26′ timber beamed ceiling, skylights running throughout the main room, and a massive gourmet kitchen.

A truly one of a kind space that creates an indescribable environment for personal & business connections, while also providing private space when desired.

It sleeps 16 people and comes in at around $750 a night, depending on the time of year.

3. Secluded Getaway With Private Beach

This is a secluded, beautiful lake home with a sandy beach right out back. Multiple levels of decking, multiple levels of interior living, yet you can find quiet nooks to be alone or have conversations.

The property is remote, yet close enough to town to go in for a movie or dinner.
The current arrangement includes actual beds to sleep 28 guests, which makes it a great place for large family or business getaway.

The house will set you back about $750 a night depending on the time of year.

4. The Aerie – Greenville

Secluded and large comfy lake home where you can come and enjoy all sorts of water sports. The house is secluded and has its own private pier and boat house.

There are lots of entertainment options for people of all ages in the house with ping pong, fosseball and all the latest entertainment systems and TVs.

With room for 16 guests and total privacy, the house is great value at just $700 a night.

5. Peaceful Retreat – North Shore Chicago

This amazing estate is perfect for corporate stays, and small gatherings of family and friends. 7 bedrooms, 6 bathrooms and even a theater seating kitchen with double ovens, double dishwashers and gas stovetop.

There is an elegant pool with rock waterfall and spa, outdoor seating, barbecue grill, grand piano and sitting room and a full size basement for family hang outs.

You will be able to sleep 14 people here comfortably and it comes in at $1,500 a night.

6. Private Mansion – Northbrook

A superb getaway for a personal or business trip. This 6,000 square foot mansion boasts luxury with an open floor plan and large room sizes

The property was just totally remodelled and is conveniently located 20 minutes from O’Hare International Airport, 30 minutes from Downtown Chicago. The Botanic Gardens, and Northbrook Court (upscale mall) are just around the corner.

The house sleeps 14 and costs just under $1,000 per night.

7. Designer Logan Square Home – Chicago

This truly one of a kind luxury experience in Chicago boasts a combined 6,000 square feet, 8 bedrooms, 5.5 bathrooms and complimentary garage parking during your stay.

Logan Square is a vibrant neighborhood filled with amazing art, restaurants and architecture. The neighborhood provides easy access to downtown while avoiding downtown hotel pricing for larger groups.

It sleeps 16 people and costs around the $1000 mark per night, depending on the time of year. The perfect base for a fun Illinois staycation.

Spending time in Illinois? We have a huge range of guides on what to do, see and eat while there.