Come Sailing, Inc.

Come Sailing, Inc. Private sailing charters on Lake Michigan in downtown Chicago. Sunset Sails, Fireworks, and Fun!

Beautiful weather crossing from Ludington MI to Milwaukee WI.
06/03/2026

Beautiful weather crossing from Ludington MI to Milwaukee WI.

It's official! CITY CAT and her crew have arrived safely in Chicago! We're home!
06/01/2026

It's official! CITY CAT and her crew have arrived safely in Chicago! We're home!

We've been spotted by one of our long time customers and friend, Nell. She snapped this photo from Lighthouse Beach in E...
05/31/2026

We've been spotted by one of our long time customers and friend, Nell. She snapped this photo from Lighthouse Beach in Evanston! Thanks Nell!

CITY CAT is almost home!! Chicago is in view! ❤️
05/31/2026

CITY CAT is almost home!! Chicago is in view! ❤️

NOW HIRING: 2026 Seasonal Deckhands & Guest Services ⛵️Come Sailing is looking for energetic, safety-conscious crew memb...
03/05/2026

NOW HIRING: 2026 Seasonal Deckhands & Guest Services ⛵️
Come Sailing is looking for energetic, safety-conscious crew members to join us on our 49-passenger commercial sailing catamaran. This is a hybrid role that combines technical seamanship with premium hospitality.
What you’ll do:
Assist with docking, line handling, and raising sails.
Provide top-tier customer service and beverage hospitality.
Maintain "yacht-standard" cleanliness of the vessel.
Help ensure a safe, memorable experience for up to 49 guests.
Requirements:
Must be 21+ (for alcohol service).
Must have (or obtain) BASSET certification.
Must be enrolled in a USCG-approved random drug testing program.
Comfortable working on the water and able to lift 50 lbs.
The Perks: 🌅 Best office views in Chicago. ⛵️ High-end hospitality experience. 📑 LOG YOUR SEA TIME! Perfect for those working toward their USCG Captain’s License or Sail Auxiliary Endorsement. We provide documented sea service letters for our crew.
📍 Location: Chicago (Lake Michigan / Navy Pier Marina) 📅 Season: Late May – September
As a premier weekend destination on Lake Michigan, our peak hours occur on Saturdays and Sundays. Candidates must be available to work at least one full weekend day (Saturday or Sunday) throughout the season.
To Apply: [email protected] or message us directly here!

Address

Chicago, IL
60603

Opening Hours

Monday 9:20am - 9pm
Tuesday 9am - 9pm
9:30pm - 11pm
Wednesday 9:30am - 9pm
Thursday 9:30am - 11pm
Friday 9:30am - 11pm
Saturday 9:30am - 11pm
Sunday 9:30am - 11pm

Telephone

+17088247245

Website

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