Come Sailing, Inc. - Chicago's Premier Private Sailing Charter
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      • Private Day Sail
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      • Private Fireworks Cruise
      • Fourth of July Fireworks Cruise
      • Private Sunset/Fireworks Sail
      • Chicago Air and Water Show
      • Custom Charters with Extended Sailing, Swimming, and Grilling
    • Shared Semi-Private Charters >
      • Shared Sailing Charter
      • Shared Sunset Sail
      • Shared Fireworks Cruise
    • Redeem Gift Certificates
  • Purchase
    • Book a Charter
    • Gift Certificates
    • SOUVENIR T-SHIRTS
    • BUILD CHICAGO W/PAPER: Four Mile Crib & Lighthouse!
  • News and Weather
    • News
    • Weather
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  • About Us
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CHICAGO AIR & WATER SHOW

CHICAGO'S PREMIER ​SAILING EXPERIENCE ​AND PRIVATE SAILING CHARTER

AIR AND WATER SHOW FOR 2021 PENDING
Click for details
Get ready for LOUD!  Get ready for SPEED!  Get ready for the BLUE ANGELS!  Headlining this year's Chicago Air and Water Show the U.S. Navy Blue Angels will thrill the crowd pushing their aircraft through spectacular demonstrations of precision flight and teamwork.

As always, this year's air show also boasts a huge line-up of other civilian and military aircraft.  Sail with us and be a part of the biggest event on the lake.  We are offering two options for Saturday and Sunday during the show.

Option #1: Private Custom Charter (4 hours plus)

Create your ultimate Chicago Air and Water Show watching package.  Chose your sailboat, choose your departure time, and choose how long we stay out on the water.  Our sailboats and captains will be available and at your disposal as early as 9:00 AM each show day.  We will tailor the sailing experience to suit your preferences.  You pick the guest list, choose the music, bring your favorite beverages & snacks, and we'll take care of the rest.  Kickback and enjoy the show. 
OTHER CHARTERS YOU MIGHT ENJOY

Private
Day Sail

BOOK NOW

Private
Sunset Sail​
​

BOOK NOW

PENDING
​
Chicago Air & Water Show


​This is a private charter.
​The passenger list is at your discretion.
The Annual
​Chicago Air & Water Show
FEATURES
  • Up to 6 Passengers
  • Three-hour Charter *
  • Departs @ 10:00 AM, 1:30 PM
  • USCG Licensed Captain
* Extend your time on the water with a
CUSTOM CHARTER
Want to throw some shrimp on the barbie or flip some burgers?  We'll be happy to setup the gas grill.  We'll be sure to have the refrigerator stocked with ice and bottled water.  And, yes, there is a restroom on board each sailboat.

If you choose to sail on our Catalina 36 sailboat, Bernard, then you have a few extra options available to you.  For instance, whether we anchor, swim, sail, it's your choice on Bernard.  Also, if you want to take a break from the sun we'll be happy to setup Bernard's large bimini cover for some time in the shade.

To book this options, please book a CUSTOM CHARTER on either Saturday, Aug. 21 or Sunday, Aug. 22.


Option #2: Private Three-hour Charter 

A thrilling three-hour charter on board either of our sailboats is a perfect choice to enjoy sailing along Chicago's beautiful lakefront with the added bonus of seeing some really amazing aircraft along the way.  To a certain extent, this charter is like a shortened version of Option #1.  We will still tailor the charter to suit your preferences.  And, you sill pick the guest list, choose the music, bring your favorite beverages & snacks.  This charter is for sailors since we just won't have enough time for some of the other activities available on the Private Custom Charter.

To book this option, simply choose a sailboat below and then choose your date and time.

Timing Notes

Thursdays and especially Fridays just prior to show weekend have traditionally been practice days for the headlining precision flight team.  While they do not publish a schedule, we are very likely to see the Thunderbirds flying around the city midday Thursday and Friday.  The official show schedules are as follows:

Saturday, August 21 @ 10 AM - 3 PM
Sunday, August 22 @ 10 AM - 3 PM

The Thunderbirds are expected to perform last each day.  Booking for these shows is available now.

Keep in mind when booking that it can take an hour to get to and from the the "show box".  While we will see planes everywhere, the area around the show box is where the best viewing will be and where you will see hundreds of boats anchored to watch the show.


Learn more about the US Navy Blue Angels.
Learn more about the US Air Force Thunderbirds.
​​Come Sailing is Chicago's premier sailing experience and private sailing charter offering a variety of boat rides, sailing charters, sightseeing tours, swimming trips, and customized private charters on Lake Michigan.  Take a break, Come Sailing, and enjoy some summer ​fun in the sun!
Your Chicago sailing and offshore adventures start here!
STEP 1 - CHOOSE A SAILBOAT
Sailing Vessel Bernard
​
Our 36 ft. Sailboat built by Catalina Yachts

$277.50/hr

SATURDAY & SUNDAY
Taxes are additional
FEATURES
  • Instant booking confirmation.
  • Spacious design with plenty of room for 6 passengers.
  • Large cockpit area with comfortable seat cushions.
  • Additional seating on sizable forward deck.
  • Swimming options available.
  • Options available for use of gas grill.
  • See more details on s/v Bernard​
​
2004 Catalina 36 MkII Sailboat s/v Bernard under sail
BOOK s/v Bernard
Sailing Vessel Druid

Our 28 ft. Sailboat built by Shannon Boat Co.

$250/hr

SATURDAY & SUNDAY
Taxes are additional
FEATURES
  • Classically charming sailboat.
  • Luxuriously adorned with elegant teak.
  • Comfortable seat cushions
  • Additional seating built into aft cockpit rail.
  • Sporty sailing characteristic with a bit of heel (lean).
  • Room for 6, but most comfortable with 4 passengers.
  • See more details about s/v Druid
​
1981 Shannon 28 Sailboat s/v Druid under sail
BOOK s/v Druid

PRIVATE SAILING CHARTERS
SUNSET SAILS • FIREWORKS • SPECIAL OCCASIONS

Come Sailing, Inc.
Chicago's Premier Private Sailing Charter
Sunset Sails, Day Sails, Fireworks Cruises, and Special Occasions

Contact Information

​
Phone:
​708-824-7245


Email:
Info@ComeSailing.us

Website:
www.ComeSailing.us
Hour of Operation

Winter
Columbus Day thru Memorial Day Weekend
No Sailing.  Phone and Email only.
Mon-Fri:  10 am - 5 pm

Summer
Memorial Day Weekend thru Columbus Day
Sailing out of Monroe Harbor
Mon-Sun:  8 am - 11 pm

SOCIAL MEDIA LINKS

Operational Locations

Monroe Harbor
Foot of Monroe Street at Lake Shore Drive
​Chicago, IL
​
Boarding Location within Monroe Harbor
Lakefront Trail along the "Charter Wall" on the north side of Monroe Harbor
Copyright © 2020.  All Rights Reserved.  Come Sailing, Inc.