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Chicago Executive Rentals & Suites

Book short- term rentals Chicago for your corporate trip

About Chicago Business Travel on StayAndPlay

Planning your next business trip to Chicago? StayAndPlay offers a wide selection of vacation rentals and short-term stays tailored to your needs. Whether you're attending a corporate golf retreat, business conference, client meeting, or working remotely, discover a diverse range of golf resorts, luxury villas, vacation rentals, and executive accommodations—from premium stays to budget-friendly options, all with excellent amenities and top-notch reviews.

Traveling with colleagues or blending business with leisure? StayAndPlay provides spacious private villas and resort accommodations in Chicago to suit groups of any size, making it easy to enjoy work and play.

Whether relocating to a new city or seeking executive housing for a month-long project, StayAndPlay connects you directly with property owners and managers to secure the best furnished accommodations in prime golf destinations.

Need to book last-minute accommodations or find a place for an extended stay in Chicago? Explore StayAndPlay’s last-minute deals, enter your travel dates, and use our filters to choose by price, accommodation type, amenities, or ratings—making your booking experience seamless.

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Frequently Asked Questions About Executive Accommodation in Chicago

There are more than 6742 places to stay in or near Chicago listed on our site, and they come with amenities like gyms, pools, and spas.
Yes. Most of our 2-5 bedroom accommodations are suitable for colleagues traveling together. Check out the option of executive accommodations in Chicago to find one that works for you.
There are more than 6742 short-term rentals in Chicago that have either a private swimming pool or an indoor pool.
There are many popular rental properties listed on our website. These include: Top 5 Places to Rent in Chicago

See all holiday rentals in Chicago on StayAndPlay.

Yes, there are many luxury vacation rentals in or near Chicago. You can book a luxury place to stay in Chicago today.