Private Sailing Charter: Chicago Lakefront Views

Embark on a private Lake Michigan sailing tour. Customize your adventure and enjoy Chicago’s skyline with a licensed captain. Book your unforgettable experience today.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Come Sailing, Inc. - We’ll depart from the north side of Monroe Harbor at our dedicated pick-up/drop-off spot. Once the safety briefing is completed and all dock lines have been brought on board, our trip will begin. The itinerary, course/route we are sailing for the day, will depend mostly on wind the direction. However, being that this is a…
What's Included
  • Use of Bluetooth speakers
  • All applicable taxes
  • Professional US Coast Guard licensed captain
What's Not Included
  • Gratuities
  • Food and Drinks
  • Parking
Additional Information

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing…

Location
East Monroe Street & South Lake Shore Drive
From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor’s edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock). Our boat’s name is BERNARD.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(60 Ratings)
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Marisa_s
Sep 5, 2024
Highly recommend - Mike was awesome! A beautiful experience on Lake Michigan! Thank you for being a great captain! Would definitely do again.
Review provided by Viator
Shawna
Sep 2, 2024
A fun, relaxing sail on Lake Michigan with an excellent Captain! Thank you Captain Mike for a lovely sail! Will be back! - Fun Safe Family Sailing in a Private Sailboat with. Great Captain. My boys and their friends visiting from out of state had a great time on the lake. Beautiful views and lovely weather and we felt safe the whole time. The boat was extremely clean and well cared for!
Review provided by Tripadvisor
U25qhvictoriap
Aug 18, 2024
Sailing cruise - The views were absolutely amazing! Captain Mike was the best and gave us an excellent sailing experience! Would definitely recommend this!
Review provided by Tripadvisor
Melissa_w
Aug 13, 2024
Great tour, super communication! - Charter Captain was wonderful. Very patient and sensitive to our needs as we were there to put my dad’s ashes in Lake MI. Highly recommend Cpt Michael for any special occasion trip or just a lovely regular sail.
Review provided by Viator
Mari
Aug 6, 2024
Come Sailing! - Lovely morning sail on Lake Michigan with the skillful, personable and knowledgeable Captain Ulysses!
Review provided by Viator
Anita_h
Aug 6, 2024
Perfect Trip! - It was a perfect trip up and down the shore with spectacular downtown views. Captain Mike was great, a perfect treat for friends to share on a warm summer day!
Review provided by Viator
Angelia_n
Aug 3, 2024
Private charter - We drove up to Chicago from Indianapolis to celebrate my husband’s 60th birthday. I wanted to find something different and fun to do. I came across this private charter and booked it. The weather was beautiful, we had such a wonderful time out on the water with Captain Mike! If you’re looking for a fun and relaxing time on the water I would highly recommend booking this excursion!
Review provided by Viator
Carolhp1497ud
Jun 22, 2024
Serene sailing with fantastic views of the Chicago skyline! - Captain Mike was fantastic and the sail was top notch, as always! This was our 3rd trip with Come Sailing and I've already booked our 4th. You will not be disappointed!!!
Review provided by Tripadvisor
W2066ylsandyt
Oct 3, 2023
Lovely sail - It was a lovely sailing. Beautiful day, the ride was relaxing, quiet except for the sound of the waves and the view so pretty. The captain was entertain, we recommend!
Review provided by Tripadvisor
Megan_f
Sep 4, 2023
Beautiful Day on the Sail Boat - The views were amazing. The Captain was very nice and professional. Such a relaxing way to spend the day
Review provided by Viator