Field Trip Chicago offers private sight-sailing charters aboard our majestic 44’ trimaran, Night Baseball. Whether you’re in the mood for a relaxing in-shore cruise or an exhilarating off-shore adventure, we’ve got you covered.

Each charter includes a professional crew—captain and skippers—along with customizable itineraries and access to a curated network of local partners who can add that perfect finishing touch to your bespoke sailing experience.

Our offerings span everything from serene leisure cruises and anchor-down celebrations to high-energy adventure sails and water-based activities. We’re all about crafting unforgettable, highly personalized moments on the Chicago lakescape—for vacationers, locals, and organizations alike.

From wellness retreats and corporate gatherings to birthdays and once-in-a-lifetime celebrations, we tailor each sail to suit your vision. Don’t see exactly what you're looking for? Submit a Save the Date request—we’ll do everything we can to bring your idea to life.

Let’s set sail!

Guidelines for Explorers

Essential Instructions

We invite you to travel light, stow your phone, and immerse yourself fully in the experience. This is your moment—be present for it. Please arrive at least 15 minutes before your scheduled sail time so you can get settled and ready to embark.

Rescheduling Policy

We sail rain or shine, but safety always comes first. If weather conditions are unsafe, we’ll work with you to reschedule or issue a full refund.
Need to make a change on your end? Let us know as soon as possible—we’ll do our best to accommodate. Last-minute cancellations or reschedule requests are tough for everyone involved, so please plan responsibly.

Charter Etiquette

Tipping: It’s customary to tip your Captain and Crew 15–20% of the charter fee. Tips are typically given to the Captain at the end of the sail, who distributes them among the Crew. The amount is always up to you and should reflect the quality of your experience. If we don’t earn it, don’t tip. But we’re confident you’ll be dazzled.

Punctuality: Being late affects not only your sail, but everyone after you. Please arrive early—cutting it close is cutting it too close.

Pro Tips for Visitors

Welcome to Chicago—the city where you can experience four seasons in a single day.

Expect:

• molasses traffic

• cryptic parking signs

• spontaneous road construction

• nonsensical street closures

• marathon detours

• perpetual festivals

• dense crowds

• lakefront cyclists with a vengeance

Please plan accordingly.