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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Sailing
    5. /Chicago 3-Hour Lakefront Sailing Cruise
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    Chicago 3-Hour Lakefront Sailing Cruise

    Sail Lake Michigan privately with skyline views and a captain

    5.0 stars• 27 reviews
    From$1,098incl. taxes and fees

    Duration

    3 hrs

    Ideal For

    Up to 7 people

    Includes

    Captain, yacht, snacks

    Highlights

    Set sail from Navy Pier Marina on a private 3-hour cruise along Chicago’s lakefront. Take the helm, swim, or relax on deck with a USCG-certified captain.

    • Choose between offshore sailing and calmer inshore cruising
    • Bring your own food and drinks, including beer, wine, champagne, or hard seltzer
    • Connect your music to the Bluetooth stereo speakers
    • Enjoy views of Chicago’s architectural landscape from the water
    • Settle into a private 37-foot sailboat with your group

    What's Included

    • USCG-certified captain
    • Private sailing yacht
    • Complimentary beverages and snacks
    • Kitchenware, fridge, and bathroom
    • Swim platform, ladder, life jackets, noodles, floaties, and towels

    Know before you go

    • All guests must sign the waiver provided in the confirmation email
    • Guests under 18 must be accompanied by a parent or guardian
    • This cruise is not recommended for people with impaired mobility
    • Weather cancellations for current or forecasted lightning or high wind are decided one hour before departure
    • A separate captain fee applies for groups of 8 or more; clarify the amount with Greetwell before booking

    Cancellation Policy

    Full refund up to two weeks before departure; 50% refund up to 48 hours before departure. Full refund if the operator cancels due to lightning or high wind.

    FAQs

    Bring layers or a rain jacket for cooler days. Wear boat shoes, sandals, or tennis shoes with non-black soles. Pack a bathing suit if you plan to swim during the Chicago Lakefront Cruise.

    Your sail may continue in passing rain, so dress accordingly. Departure delays, rescheduling, or rain checks may be available. The operator cancels for current or forecasted lightning or high wind.

    Meeting details

    Navy Pier Marina, 797 E. Grand Ave, Chicago, IL 60611

    Experience provided by On A Boat Sailing
    Experience provided by On A Boat Sailing

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #TVWCNM

    Private Charter

    $1,098.94

    Up to 7 guests for base price - Up to 12 guests for additional fee

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!

    Photo of Jonathan Garcia

    Jonathan Garcia

    June 24, 2026

    Review 1 of 1
    5/5

    Had the best time! Loved sailing on Lake Michigan on this fancy sailboat. Captain Greg is super accommodating too, helping make the experience very smooth. We also picked up catering from Reunion on the Southeast corner of the pier. Definitely making it very easy to feed our guests! Can't wait to try again but it will have to be on a Wednesday or Saturday night so we can get some shots of the fireworks!

    Photo of Jonathan Garcia

    Jonathan Garcia

    June 24, 2026

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