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.
1. choose your own adventure
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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.
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Customize your timing, route, and duration. Rates vary slightly by day and time. Need help? We’re here.
2. add some special touches
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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.
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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.
3. book your day and time
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Use the calendar to lock in your sail. If your ideal date or time isn’t available, just reach out—we’ll do our best to make it happen.
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If you’re dreaming up something our booking tools can’t quite capture, look for our Special Request button, share your vision, and our events team will do everything they can to bring it to life. We love a good challenge—and we don’t believe in “impossible.”