Chicago Executive Rentals & Suites

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.