CHICAGO'S PREMIER ​PRIVATE SAILING CHARTER
PHONE:  708-824-SAIL (708-824-7245)
EMAIL:  Info@ComeSailing.us

Your Chicago Sailing Adventure Starts Here!

Whether you are visiting Chicago or you are from Chicago, sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline that can't be beat. Kick back and let our experienced crew treat you to a relaxing sail or if you're feeling more adventurous, take a turn at the helm -- we'll be there to ensure a safe and fun experience.  Whatever your choice, our exclusive sailing charters are tailored to your preferences.


​​Our mission is to provide safe, enjoyable, customized sailing adventures for our customers.  In addition to our captains being commercially licensed by the US Coast Guard, we have been awarded a UPV Examination decal by the US Coast Guard.  The voluntary UPV Exam is a detailed and thorough review of safety systems and procedures required of commercial charter boats.

​Any boat on which you pay to be a passenger should have either ​a UCCG UPV Examination decal or a USCG Certificate of Inspection decal.  If the captain/crew cannot immediately point to one of these....ask them why not!
360' video taken while on a quick solo sunset sail.
Click/swipe around and explore.
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Sailing on a gorgeous autumn day in Chicago! Love it! - Spherical Image - RICOH THETA

​360' photo taken during a gorgeous day of sailing.
Click/swipe around and explore.

Day Sail

  • Private 2 hr sailing charter
  • Up to six passengers
  • Multiple departures daily
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
as low as $58/person

Custom Sailing Charters​

  • Private sailing charter
  • Up to six passengers
  • Flexible departures
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
Call for Pricing

Sunset Sail

  • Private 2 hr sailing charter
  • Up to six passengers
  • Daily departures
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
as low as $58/person

​Air & Water Show

  • Private sailing charter
  • Up to six passengers
  • Aug 17 & 18, 2019
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
Call for Pricing

Fireworks Cruise

  • Private 2 hr sailing charter
  • Up to six passengers
  • Wed & Sat departures
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
as low as $67/person

Fourth of July
​Fireworks Cruise

  • Private 3 hr sailing charter
  • Up to six passengers
  • Thursday, July 4, 2019
  • Departs from Monroe Harbor
  • Choice of sailboats
  • USCG licensed captain provided
as low as $100/person

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We had an excellent charter with Michael! A group of girl friends and myself went for a weekend afternoon charter and had a blast sailing along Lake Michigan! They have every accommodation on board (cooler, restroom, seating area, below deck seating) that you could need for a sail. Michael and his crew were professional and friendly to sail with- I highly recommend booking your charter here!

Robyn Szablewski - Facebook Review

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I recently went on an afternoon charter with some friends on Bernard with captain Michael, it was amazing! Michael made our group feel comfortable, safe, and helped make our time on the lake very memorable. This is the boat you want to be on to have a great time sailing along one of the world's prettiest skyline views! I would highly recommend them!

​Jamie Delos Reyes - Facebook Review

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Had a WONDERFUL birthday sailing with my family and Captain Mike was friendly and knowledgeable!!...we will definitely be sailing with him again!!#bestbirthdayever!!

​Shawn Jeffries- Cullens - Facebook Review

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Captain Mike took us out mid day and we have a beautiful day for sailing. He was so accommodating to us. He was there but you barely knew it. The boat was clean & he had refrigerator space and ice for us. We packed like we were going to two days, not two hours, and the boat didn't seem crowded. We had so much fun and can't wait to go out again! Thank you Come Sailing! Also - an added bonus is that if you park in the Millennium .....

Colleen L. - Yelp Review

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​Captain Mike made or experience so easy and amazing! We were a bit confused where to go on arrival, but another friendly boater gave us a lift to Mike's sailboat. We rented Mike's sailboat for our friends 26th birthday for a few hours on a sunny Monday, and we already cannot wait to go again. There is space in the back section of the boat to sit on benches, but me and the ladies spent the majority of our sail sprawled and sunning on the front section .....

Rebecca C. - Yelp Review

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A Fantastic Experience!  We've done a number of the Chicago boat tours, including several of the different architectural tours on large boats with crowds of people.  This was SO MUCH better!  We took my in-laws, who were visiting from out of town, on the 2-hour sunset cruise for six (the maximum allowed by the Coast Guard), and just sailed up and down the lake along the skyline. We loved it!  We lucked out with fantastic weather .....

C P. - Yelp Review

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PRIVATE SAILING CHARTERS
SUNSET SAILS • FIREWORKS • SPECIAL OCCASIONS

Contact - 708-824-7245 or Info@ComeSailing.us
Location - Monroe Harbor, Chicago, IL 60603
Copyright © 2018.  All Rights Reserved.  Come Sailing, Inc.