
Spearhead Hospitality is a Chicago-based hospitality company managing a curated portfolio of distinctive properties, including The Robey Hotel and Canal Street Eatery & Market. Driven by a passion for thoughtful design, exceptional service, and memorable guest experiences, we continue to grow with a focus on creative, community-driven destinations.

Perched above the intersection of Damen, Milwaukee, and North Avenues, The Robey rises from the iconic Northwest Tower, a 203-foot Art Deco landmark and once the only skyscraper for miles. Its 69 light-filled Tower Rooms, set within the building’s unique triangular footprint, feature warm hardwood floors and sweeping views of the neighborhood’s eclectic energy. Next door, the 20 Annex Lofts in the century-old Hollander Building offer a modern warehouse conversion experience, with flexible layouts, exposed original surfaces, polished concrete floors, and soaring 10-foot ceilings—perfectly blending historic character with contemporary design.
therobey.com
Canal Street Eatery & Market, located in Chicago’s West Loop, is a vibrant all-day destination blending a full-service eatery with a curated market. The Eatery features handmade pizzas and pastas, New American favorites, and an Italian-inspired wine list and cocktail bar, serving lunch and dinner. The Market offers coffee, breakfast, and lunch items made fresh daily, perfect for dining in or grabbing on the go. Guests can also enjoy outdoor seating and seasonal activities at the Green at 320.
canalstreetchicago.com
canalstreetchicago.com

A hidden cocktail lounge inspired by 1920s Paris hideaways. Once you find it, you don’t forget it.

Start your morning in Wicker Park at Café Robey, located on the ground floor of The Robey Hotel. Just steps from the Damen Blue Line and The 606 Trail, it’s the perfect spot for artisan coffee, all-day brunch, and cozy indoor seating with free Wi-Fi. Whether you’re a local or visiting Chicago, Café Robey is your go-to destination for a relaxed and delicious meal.

Clever Coyote is a 90s-inspired bar, irresistible wings, and bar bites collide to create a nostalgic experience like no other. Enjoy a lively atmosphere with a pool table, Street Fighter arcade game, and a Y2K and 90s playlist, perfect for reliving your favorite memories while making new ones.

Solana is your 6th-floor rooftop escape, serving poolside tacos, frozen piña coladas, and flavored margaritas, with skyline views to match. Soak up the sun, sip something delicious, and let the good vibes roll in the heart of Wicker Park.

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.

Mexico City meets JapanAfter World War II a large number of Japanese immigrants arrived in Mexico City laying the foundations of what is now known as Mexico City’s little Tokyo.
Embracing the progression from colonial outpost to modern metropolis, we incorporate familiar elements of the diverse cultural and culinary heritage to create a list of avant-garde cocktails featuring classics reinterpreted with Mexican-Japanese inflection.
Careers
We’re always looking for exceptional people who want to work across our portfolio of lifestyle hospitality properties. There are countless opportunities to share your passion for hospitality, care about every detail of the guest experience, and thrive in a collaborative team environment.
Bartender/Server Hybrid at Valedor
Seasonal Overnight Engineer at The Robey
Housekeeper at The Robey
If you’re interested in joining us, apply now by emailing your resume to HR@SpearheadHospitality.com
Additional job listings may be found on our LinkedIn page