Chicago, IL

A world-class city where architecture, access, and elevated experiences come together for unforgettable offsites

Why You'll Love It Here

Set along Lake Michigan, Chicago delivers a rare mix of architectural beauty, culinary depth, and big-city accessibility. It’s a destination where teams can move seamlessly between high-level strategy and one-of-a-kind experiences, from private stadium access to iconic riverfront moments. Ideal for groups that want energy, sophistication, and standout programming.

Where You'll Stay

St. Regis Chicago

Modern and striking, The St. Regis brings a design-forward edge with panoramic views of the skyline and lake. It’s perfect for teams looking for a contemporary, high-impact setting with memorable gathering spaces.

The Peninsula Chicago

Polished and quietly luxurious, The Peninsula is ideal for executive retreats that require precision, discretion, and elevated service. Rooftop spaces and refined meeting rooms create a strong balance of productivity and experience.

Four Seasons Chicago

A classic luxury anchor with newly refreshed spaces, the Four Seasons offers comfort, consistency, and lakefront views that ground the experience in calm and focus.

What You'll Do

Private Dinner on the Field at Wrigley Field

Step onto one of baseball’s most iconic fields for a fully private dining experience. Teams enter through player areas, walk the dugout, and dine on the field or in an exclusive club space. It creates a sense of scale and exclusivity that’s hard to replicate, making it ideal for milestone moments or opening-night impact.

Golf Experience at Olympia Fields Country Club

Host a private golf outing at a championship-level course known for elite play and pristine conditions. Whether it’s a structured tournament or relaxed networking rounds, the setting encourages organic conversation, relationship building, and a slower, more intentional pace.

Elevated Architectural River Cruise

Elevate the classic architecture tour into a fully private experience with onboard dining and curated storytelling. As teams move through the city’s architectural history, the setting naturally sparks conversation and fresh thinking in a way traditional meeting rooms cannot.

Your Itinerary

Day 1


Morning: Arrival and check-in at The St. Regis Chicago


Afternoon: Opening session and strategy alignment


Evening: Private dinner experience on the field at Wrigley Field

Day 2


Morning: Team breakouts and working sessions


Afternoon: Architectural river cruise with private dining


Evening: Group dinner and rooftop cocktails

Day 3


Morning: Closing breakfast session


Afternoon: Optional golf outing at Olympia Fields Country Club


Evening: Departures

Ready to Have Some Fun?

Get StartedGet Inspired