Two Brothers Sailing Chicago provides unforgettable sailing adventures on Lake Michigan. Operating from Lombard and Chicago areas since our founding, we've welcomed countless guests aboard our unique fleet including the Blue Moon, one of only 40 ever made, creating memorable experiences on the shimmering waters.

  • Do you provide life jackets?

    Yes, we provide all necessary safety equipment including USCG-approved life jackets for every passenger. Your safety is our top priority during your Lake Michigan sailing adventure.

  • What should I wear for sailing?

    Wear comfortable clothing and non-slip shoes like sneakers or boat shoes. Bring a light jacket as it's cooler on the lake, especially during sunset tours.

  • Can we bring food and drinks?

    Yes, you're welcome to bring food and beverages aboard for your sailing tour. Please contact us to discuss any specific needs for your group.

  • What's the maximum group size?

    We accommodate various group sizes depending on your chosen vessel. Our Blue Moon and other boats in our fleet can handle different party sizes for private charters.

  • Do you offer sunset tours?

    Yes, sunset sailing tours are among our most popular offerings. Experience the breathtaking views of Chicago's skyline as the sun sets over Lake Michigan.

  • Where do tours depart from?

    Tours depart from our convenient Chicago location at 601 W. Montrose Ave., Chicago, IL 60613. We serve the Lombard and greater Chicago area.

  • What happens if weather is bad?

    Safety comes first. If weather conditions are unsafe for sailing, we'll work with you to reschedule your tour or provide alternative arrangements.

  • Do you offer private charters?

    Yes, we specialize in private sailing charters perfect for romantic getaways, special celebrations, or group adventures on Lake Michigan's beautiful waters.

  • How far in advance should I book?

    We recommend booking as early as possible, especially for sunset tours and weekend sailing adventures. Call (630) 816-1427 to check availability for your preferred date.

  • Is sailing experience required?

    No sailing experience is necessary! Our experienced captains handle all the sailing while you relax and enjoy the stunning views of Chicago from Lake Michigan.

Ready to set sail on your Lake Michigan adventure? Call Two Brothers Sailing Chicago at (630) 816-1427 to book your unforgettable sailing experience today. Whether it's a romantic sunset cruise or group adventure, your perfect sailing tour awaits.