We are Chicago based hospitality company that manages a diverse portfolio of properties, including the renowned The Robey Hotel, the vibrant Chicago Getaway Hostel, and the bustling Canal Street Eatery & Market. With a commitment to excellence and a passion for creating unforgettable moments, Spearhead Hospitality continues to expand its reach, with potential for managing additional properties in the future.



Perched high above the big intersection of Damen, Milwaukee and North Avenues in an Art Deco masterpiece formerly known as the Northwest Tower—stretching 203-feet tall and the only skyscraper for miles—The Robey captures the storied spirit of Chicago: a bustling, ever-changing, big-shouldered town.


Getaway Hostel reinvents the hostel for the modern wanderluster without breaking the bank. Pairing hotel-style services with killer specials, this prime spot in Chicago’s historic Lincoln Park elevates the experience with a list of freebies like WiFi, communal kitchen, free coffee bar, weekly social events, and much more!


Canal Street Market & Eatery, located in Chicago’s West Loop, is an all-day market with coffee, breakfast, and lunch, as well as an Italian bar and restaurant offering lunch and dinner. At the market, guests can order breakfast and lunch items made fresh, or grab something on the go. The Eatery offers handmade pizzas, pastas, New American favorites, as well as an Italian-inspired wine list and cocktail bar. Guests can enjoy outdoor seating and activities at the Green at 320.


Afterbar is an intimate cocktail lounge overlooking the park at 320 S Canal. The menu is helmed by Laine Peterson and Jeromiah Liver and features classic and creative cocktails, wine, beer and bar snacks.


Our neighborhood cafe serves up Chef Michael Elliott’s seasonal comfort food – against the backdrop of Wicker Park and Bucktown’s bustling six-corner intersection. Join us for all-day brunch, every day of the week.


Clever Coyote is a 90s-inspired bar where tiki-inspired drinks, steamed buns reminiscent of classic sandwiches, and irresistible wings collide to create a nostalgic experience like no other. Celebrate the youthful nostalgia of the 90s, inviting you to relive your favorite memories and create new ones in an atmosphere that embraces the spirit of the past while celebrating the present.

Visit Clever Coyote

Cabana Club is open to all—because with 180-degree views of the skyline, we couldn’t keep it all to ourselves. To the East you’ll spot Chicago’s 1,127-foot high John Hancock building as well as the tops of more earthly neighborhood churches. You may even catch a glimpse of a passing L train or two—the Damen Station is right here. Chicago natives and citizens of the world welcome.

Visit Cabana Club

Sitting atop the tallest building for miles, our stunning rooftop 13th floor lounge is sure to leave you feeling lucky (thanks to those twinkling skyline views). Stretch out across low sofas next to the bar—or venture outside to the terrace where you’ll see The Robey’s heavens-bound spire. As the name suggests, we’re up for anything and always down for a nightcap.

Visit The Up Room


We are always on the lookout for exceptional people that want to work in the lifestyle hotel space. With 89 rooms and 4 food and beverage outlets, there are many opportunities to share your pride for hospitality. We are a results driven hotel that loves to hear from those who care about every detail of the guest experience and enjoy working in a team environment.

We are always looking for qualified candidates; Apply Now! Please email your resume to HR@SpearheadHospitality.com

Additional job listings may be found on our LinkedIn page