Starting Line Strategies
Feb
21
9:00 AM09:00
Seminar

Starting Line Strategies

  • Chicago Corinthian Yacht Club (map)
  • Google Calendar ICS

CCYC | 9 am — 12 pm

A panel of fast and slippery sailors will discuss starting your races cleanly and quickly, with a review of the Racing Rules of Sailing that apply to the start line.

We will also have a presentation of the Vakaros Race Sense system, starting instruments bringing GPS accuracy to your starts and taking the guesswork out of OCS calls.

The seminar is FREE. Breakfast treats and coffee will be provided. 

RSVP to sfink26340@aol.com

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Racing Rules Up and Down the Race Course
Feb
28
9:00 AM09:00

Racing Rules Up and Down the Race Course

ColYC | 9 - 11 am (with bonus virtual session 11 am -12 pm)

Sharpen your racing skills with a guided review of the sailing rules that matter most – from pre-start to the finish line. 

We’ll explore the critical moments on the race course: pre-start, fair positioning, upwind tactics, making smart legal weather-mark approaches without violating Mark Room rules, downwind strategies, lee-ward mark roundings, and finishing protocols. 

Perfect for racers of all levels looking to sail smarter and avoid costly mistakes on the course, and either avoid the protest room or prevail if you end up there. Includes bonus session on How NOT to Lose in the Protest Room.

Event is Free.


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Boating Safely in Illinois: Official IDNR Safety Class
Feb
15
9:00 AM09:00
Seminar

Boating Safely in Illinois: Official IDNR Safety Class

  • Chicago Corinthian Yacht Club (map)
  • Google Calendar ICS

CCYC | 9 am—5 pm

If you operate a motorboat over 10HP and were born on or after Jan 1, 1998, you are required to have a Boating Safety Education Certificate. This 8-hour, in-person course will teach you

·   Boating Basics: Rules of the road, navigation, and equipment.
·   Safety First: Emergency measures and PWC operation.
·   Legal Requirements: Illinois boating laws and registration. 

The instruction will be provided by local IDNR instructors.

Certification: Receive your official IDNR Certificate of Competency.

FREE-But you must register so there are enough materials for all.

Note: Ages 12 - 18 must be accompanied by a parent or guardian

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Navionics Info Session
Jan
17
9:00 AM09:00
Seminar

Navionics Info Session

Jackson Park Yacht Club
6400 South Promontory Drive
Chicago, IL, 60649

10:00 am
Navigate the digital seas with our Navionics Class at JPYC. Join our off-the-water session to master electronic navigation tools, chart interpretation, and GPS integration. Whether you're a beginner or seasoned sailor, this class is your key to confident on-water precision. Secure your spot now and sail into a new era of navigational expertise!

Members $10 | Non-members $20

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Strategies & Tactics on the Mac

Chicago Corinthian Yacht Club
601 W. Montrose Ave.
Chicago, IL, 60613

9:00 am — 12:00 pm
Hear our panel of experienced and successful Mac racers discuss strategies, tactics, and equipment to help you have your best race this year. Featured speaker Blane Boynton will be focusing on installing and using an AIS transponder, as well as the benefits of adding Starlink to your arsenal. Have questions? Send them in advance along with your RSVP!

THE SEMINAR AND DONUTS ARE FREE! 

RSVP to sfink26340@aol.com

ZOOM >

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End of the Year Party & Town Hall Meeting
Nov
14
6:00 PM18:00

End of the Year Party & Town Hall Meeting

ColYC | 6:00 pm

Join us at CASRA's annual Town Hall Meeting to discuss survey results, hear comments about the season, and discuss ideas for 2026. The Town Hall will be followed by the awards party with food, drink, and flags. But first, CASRA needs your input! Please complete our Survey and make sure to forward it to your crew as well. Everyone responding to the survey will receive a FREE DRINK at the End of Year Party.

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Fall Closer
Sep
27
12:00 PM12:00
Distance (Nearshore), Buoy

Fall Closer

  • Chicago Corinthian Yacht Club (map)
  • Google Calendar ICS

The last race of the season.  Come out for buoy and nearshore distance courses to celebrate the last of the offshore races for 2025.  Sailing is great in the fall with warm water, big air and the chance to pick up a win to top off the season.  Your boat deserves an outing on the water.  Winter will soon be upon Chicago so make the most of a great day.

Buoy, Distance (Nearshore)

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3 Crib Fiasco
Sep
20
4:30 PM16:30
Distance (Nearshore)

3 Crib Fiasco

The 3 Crib Fiasco is a fun race where boats round 3 Chicago City water cribs in whatever direction skippers want.  Blustery September winds and dodging boats rounding the course in the opposite direction are par for the course.  Awards and a party are held at Columbia Yacht Club after racing.

Distance (Nearshore)

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Polonia Cup
Sep
14
3:30 PM15:30
Buoy, Distance (Nearshore)

Polonia Cup

  • Chicago Corinthian Yacht Club (map)
  • Google Calendar ICS

This single-day regatta has grown from a weekend party at Montrose Harbor thrown by the Polish Yacht Club to a full offshore event with nearshore distance and buoy racing.  There will be a dinghy circle as well.  This race always features a terrific party back at Chicago Corinthian Yacht Club and all racers are invited.

Buoy, Distance (Nearshore)

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Michigan City to Chicago
Sep
1
4:00 PM16:00
Distance (Port to Port)

Michigan City to Chicago

Chicago’s yearly nighttime trek to St. Joe is a must-sail port-to-port race for all boats in southern Lake Michigan.  The 50-mile race starts at dusk on a Friday in Chicago and ends the next day in St. Joe.  Following racing on Saturday join the legendary party at St. Joseph River Yacht Club and other activities.

Distance (Port to Port)

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St. Joe to Chicago
Aug
31
4:00 PM16:00
Distance (Port to Port)

St. Joe to Chicago

Jackson Park Yacht Club
6400 South Promontory Drive
Chicago, IL, 60649

Chicago’s yearly nighttime trek to St. Joe is a must-sail port-to-port race for all boats in southern Lake Michigan.  The 50-mile race starts at dusk on a Friday in Chicago and ends the next day in St. Joe.  Following racing on Saturday join the legendary party at St. Joseph River Yacht Club and other activities.

Distance (Port to Port)

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ST JOE TO MICHIGAN CITY

Burnham Park Yacht Club
1500 South Linn White Drive
Chicago, IL, 60605

Chicago’s yearly nighttime trek to St. Joe is a must-sail port-to-port race for all boats in southern Lake Michigan.  The 50-mile race starts at dusk on a Friday in Chicago and ends the next day in St. Joe.  Following racing on Saturday join the legendary party at St. Joseph River Yacht Club and other activities.

Distance (Port to Port)

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Chicago to St. Joe
Aug
29
4:00 PM16:00
Distance (Port to Port)

Chicago to St. Joe

Chicago’s yearly nighttime trek to St. Joe is a must-sail port-to-port race for all boats in southern Lake Michigan.  The 50-mile race starts at dusk on a Friday in Chicago and ends the next day in St. Joe.  Following racing on Saturday join the legendary party at St. Joseph River Yacht Club and other activities.

Distance (Port to Port)

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Third Coast Cup — CANCELLED
Aug
16
to Aug 17
Distance (Port to Port)

Third Coast Cup — CANCELLED

Chicago Corinthian Yacht Club
601 West Montrose Avenue, Chicago, IL, 60613

Burnham Park Yacht Club
1500 S Linn White Dr, Chicago, IL 60605

Chicago Corinthian Yacht Club and Burnham Park Yacht Club combine to offer a weekend of port-to-port racing from Chicago up to Winthrop Harbor.  Boats stay at Northpoint Marina with a party organized by the very friendly Winthrop Harbor Yacht Club.  Close by are the Tropic Bar and on the south end of the marina visit Harbor Brewing Lakeshore.  The racing is along the North Shore and the course is only 6 miles or so further than Waukegan.

WHYC is offering a pasta bar to racers for $30.00 per person.  They would like people to register.  Here is the link to their website.  Click and go to the pasta bar registration:

Distance (Port-to-Port)

EVENT CANCELLED

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100 Boats on a Beer Can
Aug
5
to Aug 6
Beer Can, Buoy, Distance (Nearshore)

100 Boats on a Beer Can

CHICAGO RACE WEEK

Tuesday night feeder races from the North and South harbors with a beer can in the middle as the fleets converge to celebrate and anticipate Wednesday night's roller coaster ride of the Summer!  Its got a mass start; 100 boats all aiming for space on the course off the line; sheer fun!  sheer terror!  Great parties both Tuesday and Wednesday evenings.  This is the race you do not want to miss.  A special thanks to Skyway Yacht Works for being a named sponsor for the 100 Boats on a Beercan this year!   This year, we will be using Railmeets for registration and scoring of the event.   We have decided to use Railmeets for this event as it allows us to better manage the different starting areas for the Tuesday feeder races and quickly combine the results for the main race on Wednesday.  We have created a guide on how to register using Railmeets (https://static1.squarespace.com/static/58121d166a4963a8ebff82c5/t/6683f451de61272abe0c1b97/1719923793806/100_BOATS_24_How_to_register.pdf)  Even if you have used Railmeets before to register for a regatta, we encourage you to read over the howto guide as it has details to properly register and denote your requested assignments for the Tuesday and Wednesday races. More information and registration links are available at https://chicagosailracing.org/100-boats-on-a-beer-can

Buoy, Distance (nearshore)

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Rainbow Regatta (Charity)
Jul
12
9:30 AM09:30
Distance (Nearshore)

Rainbow Regatta (Charity)

Hosted in conjunction with Rainbow Races, Inc., an organization that seeks to connect the LGBTQ+ community and its allies through fundraising and awareness events; and promoting equality through sailing. The Rainbow Regatta is a casual event open to all sailors and encourages those interested in sailing to join. It aims to be a fun event on the water that builds friendships and encourages equality. 

In the spirit of the casual and fun nature of this race, we have changed the starting sequence for the race from the traditional 5-minute starting sequence to a casual 15-minute starting window (full details are listed in the amendment).   While the starting window is open, a boat in any section can cross the start line at any time for its start.  The race committee will record the starting time for each boat, individually, and the elapsed time for each boat will be calculated based on their starting time.  The corrected times, for PHRF handicapped boats, and places will be determined as a normal race. 

Distance (Nearshore)

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Chicago to Waukegan
Jun
21
2:30 PM14:30
Distance (Port to Port)

Chicago to Waukegan

A port-to-port race that most racers do not want to miss- its an old reliable.  More so this year as the Waukegan Yacht Club is back in their clubhouse and ready to put on a great party to celebrate.  They are gearing up to welcome about 100 boats with live music, terrific food, and a start for the fleet sail back to Chicago on Sunday.  Don't miss this weekend event.

Distance (Port to Port)

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Gold Star Regatta (Charity)
Jun
14
2:30 PM14:30
Distance

Gold Star Regatta (Charity)

Come out on Saturday, June 14th to race in the 2025 Gold Star Regatta and show your support for the surviving family members of our fallen Chicago Police Officers. Your participation in the Gold Star Regatta honors our fallen Officers and reminds the surviving families that they are not forgotten. The Gold Star Race is the sailing community's opportunity to give back to our Officers who make enormous sacrifices for our safety. Your simple participation in the race is all it takes. We hope to see you at the start line Saturday morning. Thank you for your support.

Distance (nearshore)

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Colors
May
31
to Jun 1
Buoy, Distance (Nearshore)

Colors

Shake out the sheets and challenge your skills against the best skippers in Chicago in both Buoy and Distance events.  

  • Buoy event on Saturday, May 31st and Sunday, June 1st

  • Distance event on Saturday, May 31st

  • Party and awards both afternoons after racing with rafting available at the dock.

Buoy, Distance (Nearshore)

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