how it works

At Field Trip Chicago, we value flexibility and customization just as much as you do. But we also understand how precious your time is. That’s why we’ve worked hard behind the scenes to set you up for success, so you spend less time planning and more time adventuring. Our streamlined 3-step booking process offers full customization while also providing hassle-free, all-inclusive sail packages—saving you both time and mental energy. We’ve done the research and put in the work, so you can jump straight to the fun part.

Less planning. More adventuring.

White sailboat on Lake Michigan with people onboard, clear blue sky background.

1. choose your own adventure

  • We get it—you don’t need one more thing to plan. That’s why we’ve curated a collection of our favorite, most-loved sails. We’ve handled the details and done the thinking for you, so all you have to do is show up and enjoy a seamless, stress-free adventure.

  • Go for it! Start with an hourly sail and customize the when, where, and how long. Rates may vary slightly based on the day and time, and we’re always here to help if you need a hand.

2. add some special touches

  • Sailing makes us hungry. After months of culinary trial and error, we’ve figured out the best boat-friendly bites—and teamed up with some of Chicago’s finest to bring them on board.

  • Some moments deserve more than a playlist and a phone camera. When your celebration calls for live music and professional photography, this is the place to look. We’ve partnered with top local talent to help make your day truly unforgettable.

Close-up of a June calendar showing the dates 22 to 26, with partial visibility of days Monday and numeric dates 13 and 20.

3. book your day and time

  • Ready to book? Head to the calendar to lock in your sail. If your ideal date or time isn’t available, don’t worry—just call, email, or fill out a special request form. We’ll do our best to make it happen. We’ve got you.

  • If your ideal date isn’t available—or you’re dreaming up something our booking tools can’t capture—this is the place to be. Fill out our special occasion request form, share your vision, and our events team will do everything they can to bring it to life. We love a good challenge and don’t believe in “impossible.”