The 2021 Great Lakes Intercollegiate Offshore Regatta was held September 25-26 in Chicago, IL. The event was co-hosted by the Storm Trysail Club and Columbia Yacht Club with support from the Chicago Tartan 10 Fleet and the Chicago J/105 Fleet. This year 18 college teams participated in the competition alongside owners, coaches and organizing staff. The event saw over 160 individuals involved in total. Five races were completed on day one, but by race three the average wind speed was over the spinnaker limit of 15 knots and the "E" flag was displayed, racing without spinnakers ensued. However, the final race had the winds back down and the "E" flag was struck and teams could once again fly spinnakers. At the end of the day, the University of Michigan was in the lead for the J/105 fleet. On day two, competitors awoke to winds from the southwest, initial WSW and later stabilizing to more a more southerly SW/SSW. Wind speeds were hovering around 13-15 knots and the harbor start occurred at 0900 as scheduled. The PRO was able to kick off three more races before the 1400 no racing time set by the notice of race. Teams lamented "fluky winds" this day as the PRO battled to maintain a relatively square course. Spinnakers were allowed at all times and at the end of the day, the University of Michigan continued their streak and was able to secure first place in the J/105 fleet.
- University of Michigan-5-3-1-1-2-5-2-1; 20
- University of California San Diego-4-2-4-4-3-3-4-3; 27
- University of Rhode Island-1-5-6-6-6-1-1-2; 28
- United States Naval Academy-6-1-5-3-5-2-3-5; 30
- United States Coast Guard Academy-3-4-2-2-4-4-6-7/RET; 32
- University of Wisconsin Madison-2-6-3-5-1-7/RET-5-4; 33