Chicago Triathlon & Run Training Group Events
Grit Endurance Coaching Events
Connect with the triathlon community and boost your performance at our events and training sessions. As part of Chicago’s premier triathlon training club, you get access to our team events and training sessions year-round. From open water swims to indoor triathlon training at FFC Union Station, Grit Endurance offers a diverse calendar for all levels.
Check out our monthly events, Chicago area and Midwest races where we’ll have a presence, and other triathlon club opportunities!
Grit Endurance Weekly Training Events
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Group Track Run Workouts
Every Wednesday morning & evening from April through September
6:00-7:00am at Montrose Ave & 6:00-7:00pm at Dunbar Park
Looking for run training in Chicago? Join the Grit Endurance team for a fun and challenging outdoor speed running workout every Wednesday from April to September!

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Group Open Water Triathlon Swim Workouts
Every Friday from June through August
6:00-7:00am at Ohio Street Beach, Chicago
Start your Friday mornings this summer with triathlon swim training! The Grit Endurance team hosts a structured open water swim each Friday from June through August!

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Group Indoor Triathlon Swim Workouts
Mon & Thu evenings and Wed mornings at FFC Union Station; Tue & Thu mornings at FFC Gold Coast
Join our year-round tri swim program to build fitness and improve your swim technique. Classes are at 6:00pm on Mondays, 6:30am on Wednesdays, and 5:30pm on Thursdays!

Additional Upcoming Club Events
June Monthly Fun Run, Zone 2 Book Crew & Pleasant Prairie Shakeout
June is kind of a crazy busy month, so we’re combining our Monthly Fun Run with our Zone 2 Book Crew Run! Not only that, we’re also adding in a Pleasant Prairie Triathlon Shakeout Run, all at the same time! So don’t miss out on the fun. We’ll meet at Necessary & Sufficient Coffee downtown, run through Grant Park and to the lakefront trail, returning for breakfast and coffee afterwards. Need more miles, start your run early and meet us at 9!
For those interested in the June book of the month for Zone 2 Book Crew, it’sThe Lion Women of Tehran by Marjan Kamali!
Pleasant Prairie Triathlon
Come join us for this awesome race that is only a 50-minute drive from downtown Chicago! They offer sprint, Olympic, duathlon and relay options! See more info here!
July Group Fun Run
Come join us for a different perspective on the Group Run and our great city. This month we will meet at Palmisano Nature Park (W. 27th St. and Halsted - plenty of street parking) at 9 AM and enjoy a warmup run through the streets of the Bridgeport neighborhood, followed by a challenging hill run workout in the park for a unique view of the skyline. Afterwards, a short cool down jog will lead to Jackalope Coffee and Tea House (735 W 32nd St) for refreshment!
July Group Bike Ride
Join us for our July monthly group ride! The meetup location and route is coming soon! All levels are welcome, and there will be 3 pace groups: 14-16 mph, 17-19 mph and 20+ mph. After the ride, we can hang out for some lunch and brews! All riders must be a GE team member and have signed a waiver prior to attending. Please arrive 15-20 minutes before 8:00 to get ready, as we will leave promptly at 8am! Reach out to Jim@grit-endurance.com for more info!
Grit & Sprint Triathlon
Gain some valuable triathlon race experience with this beginner friendly event! We will be doing an “informal” sprint distance triathlon along the Chicago lakefront! The race will consist of an 800-meter swim, a 15-mile bike, and a 5K run!
Naperville Triathlon & Duathlon
Come join us for this fun event in the Western Suburbs! This is a great race for beginners as well as experienced athletes!
USA Age Group Nationals
We’re heading to Milwaukee for AG Nationals, which includes sprint, olympic and relay formats!
Ironman Wisconsin Course Ride
Whether you are training for a fall Ironman or 70.3, or just want a serious challenge, join us for this group training ride on the beautiful and hilly IM Wisconsin course! This year, we are partnering up with Vision Quest, and we will have a fully stocked SAG stop at Cross Plaines with hdyration and nutrition products to keep you fueled and rolling strong!
Chicago Triathlon Watch Party
Come race with us or root on the team at the world’s largest triathlon! We will likely have over 40 GE athletes racing, so it’s going to be a whole lot of fun!
August Group Fun Run
Our August Group Run location is TBD. We will meet at 9am, and then run for about an hour out and back on the trail. Afterwards, we’ll hang out and have some coffee and breakfast! If you want to run more miles, feel free to knock out some miles ahead of time!
September Group Bike Ride
Join us for our September monthly group ride! The meetup location and route is coming soon! All levels are welcome, and there will be 3 pace groups: 14-16 mph, 17-19 mph and 20+ mph. After the ride, we can hang out for some lunch and brews! All riders must be a GE team member and have signed a waiver prior to attending. Please arrive 15-20 minutes before 8:00 to get ready, as we will leave promptly at 8am! Reach out to Jim@grit-endurance.com for more info!
Ironman 70.3 Wisconsin
Come race this amazing event or get inspired as part of the GE cheer crew!
Ironman Wisconsin
Come race this amazing event or get inspired as part of the GE cheer crew! We will have the tent up and will be supporting the athletes throughout the day!
Ironman 70.3 Michigan
Join us for this awesome race in beautiful northern Michigan, the views and experience will not disappoint!
Grit Endurance Fall Social
Join us for our annual GE fall social at Midwest Coast Brewing! Friends and family are welcome! We will have a private room reserved upstairs from 3:30 - 6:30 as well as access to their beautiful rooftop patio, which has a retractable roof in the event of rain. Food will be provided by Grit Endurance and beverages can be purchased from the brewery! No RSVP required, come and go as you like!
Chicago Marathon Watch Party
Come out and join the GE crew for our watch party on course! We will have the tent up near Morgan Street Cafe at the corner of Morgan and Adams, where you can see runners pass by twice at about mile 14 and 17. The lead runners are expected around 8:30am. GE will provide donuts and coffee starting at 8am!
Ironman 70.3 Rockford
Come race or support this great event with us! See more info on the race and registration here!
GE Spectator Race-Day Plan: Davis Park will be the best location to watch the swim exit and the bike out and in, and to watch the runners exit T2. We plan to set up the Grit Endurance tent in Beattie Park to support the run, where spectators will have 4 opportunities to see their athletes pass by! This can also be used as a meeting location for athletes and friends/family after the race!
June Group Bike Ride
Join us for our June group ride! The meetup location for this ride will be Hardware Sustainable Gastropub & Brewery in Aurora! All levels are welcome, and there will be 3 pace groups: 14-16 mph, 17-19 mph and 20+ mph. The full ride route is 49 miles, but anyone riding less distance can turn around at any point. Here is the Garmin course route, please download it ahead of time if possilbe. After the ride, we can hang out for some lunch and brews! All riders must be a GE team member and have signed a waiver prior to attending. Please arrive 15-20 minutes before 8:00 to get ready, as we will leave promptly at 8am! Reach out to Jim@grit-endurance.com for more info!
Bike Maintenance & Fix A Flat Clinic
Our friends at Mox Multisport are offering a free bike maintenance and fix a flat clinic at 6pm on June 11th! This will be perfect for beginners and anyone who would like to get a better understanidng of some bike maintenance basics! Also, if you need a tuneup, remember that as a GE member you get 30% off bike service!
Ironman 70.3 Omaha
Come race or support this new event with us in 2026! More information and registration can be found here.
Chicago 13.1 Watch Party
The Bank of America Chicago 13.1 offers runners a unique experience, bringing a world-class half marathon to the neighborhoods of Chicago’s West Side. The 13.1-mile course weaves through the historic parks and boulevards of the West Side, starting and finishing in Garfield Park with scenic loops through Humboldt and Douglass Parks.
May Group Bike Ride
For our May group ride, we are pumped to be going to the Arlignton 500, hosted by the Arlington Heights Bicycle Club! The Arlington 500 is a recreational bike ride on scenic roads in Lake County. The cumulative routes are 20.2, 43.9, 59.3, 83, and 100.8 miles. The routes are marked and designated with colors on the route markers. Included with registration are downloadable GPS routes and/or cue sheets. This is a supported ride and with provided food and beverages at the rest stop. On-site restrooms are available at the registration / rest stop.
Zone 2 Book Crew Group Run - May
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
GE Spring Camp
Come swim, bike and run with us on portions of the beautiful and challenging Ironman courses in Madison. Whether you are training for a short or long course race this year, or just looking for a fun weekend adventure, this camp is the perfect pre-season opportunity for you to take your fitness to the next level!
May Group Fun Run
Our May Group Run location is thanks to GE Coach and IronWoman Extraordinaire, Sarah Beerman! We’re heading to the beautiful Ravenswood neighborhood! We will meet at 9am at the Eco Flamingo Market Cafe (4754 N. Rockwell), and then run for about an hour out and back on the North Shore Channel Trail. Afterwards, we’ll hang out and have some coffee and breakfast! If you want to run more miles, feel free to knock out some miles ahead of time!
Zone 2 Book Crew Group Run - April
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
April Group Bike Ride
Join us for our first monthly group ride of 2026! The meetup location for this ride will be Werk Force Brewing, at 14903 S. Center St., in Plainfield. All levels are welcome, and we will do an out and back route on the rural roads west of Plainfield, so you can do any distance up to 69 miles!
April Group Fun Run
Our April Group Run is being “hosted” by GE legend, Maggie Benhart! We’ll be heading to beautiful Waterfall Glenn! Park at the main parking lot off of Cass Avenue, just south of I-55. We will meet at 9am, and then run for about an hour out and back on the trail. Afterwards, we’ll head to Blueberry Hill Breakfast Cafe! If you want to run more miles, feel free to knock out some miles ahead of time! The full trail loop is about 9.5 miles, so this one is going to be perfect for those of that are deep in training!
CHI Town Half Marathon & 10K
Join us for this great local running event along Chicago’s lakefront! Registration and more info here!
Zone 2 Book Crew Group Run - March
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
Shamrock Shuffle
Shamrock Shuffle with Grit Endurance!
Kick off the spring running season in style with this epic event in downtown Chicago! Registration and more info here!
March Group Fun Run
Our March Group Run location is taking us to Bucktown and the 606 trail! We will meet at 9am at Goddess and the Grocer (1649 N. Damen), then run for about an hour on the trail, returning back to the cafe for breakfast and coffee around 10:00! If you want to run more, feel free to knock out some miles ahead of time!
Interested in showing off your favorite coffee shop and run route? Reach out to us with your ideas and we will likely include it for a future run!
Grit Endurance Hits the Slopes!
Join your fellow Grit Endurance athletes for fun and camaraderie on the slopes! Embrace the thrill of winter by joining us to ski or snowboard - the perfect way to stay active during the triathlon off-season! Whether you’re a seasoned skier, an adventurous snowboarder, or just looking to try something new, this event is for you! As usual, friends and family are welcome!
Team Trivia Night!
Ready for a night of fun, friendly competition, and socializing? Join us for Trivia Night on Thursday, February 13that 7:30pm at O'Donovan's Pub. It's the perfect opportunity to relax, bond with your teammates, and show off your trivia skills (or lack thereof). Whether you're a trivia pro or just in it for the fun, everyone is welcome!
February Group Fun Run & Mobility Session
Our February group run is taking us to Lincoln Square, and includes a bonus dynamic stretching and mobility session afterwards with DPT, Erin Short! We are going to meet at Morning Bird Studio (3738 N . Lincoln) at 9am, run for an hour on the North Shore Channel Trail, then return back to Morning Bird at 10am for a 45-min mobility workout. Afterwards, we’ll head to Mimi’s Cafe next door for food, coffee and hanging out!
F3 Half Marathon & 5K
Join us for some frosty fun on the lakefront! This is a great race because you can warm up before the race and warm up again after the race indoors at Soldier Field! Registration and more info here.
Zone 2 Book Crew Group Run - January
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
WhirlyBall & Bowling
Due to inclement weather (ah, Midwest winter 🙃), we’re making a game-time adjustment to this weekend’s plans. Instead of ice skating, we’ll be heading to WhirleyBall Chicago (https://www.whirlyball.com/chicago) for some indoor fun! We’ll kick things off with WhirleyBall from 2:00–3:00pm, followed by an hour of bowling starting at 3:15pm. Please plan to arrive by 1:45pm so we can get everyone checked in and ready to roll.
Because of game size restrictions, this event is for Grit athletes only. If you’re planning to attend, please email or text Coach Whitney as soon as possible at Whitney@grit-endurance.com or (608) 295-1869.
Team Trivia Night!
GE Athletes, get ready for a night of fun, friendly competition, and socializing! Join us for Trivia Night on Tuesday, January 6th at 7:00pm at Eris Brewery and Cider House. It's the perfect opportunity to relax, bond with your teammates, and show off your trivia skills (or lack thereof). Whether you're a trivia pro or just in it for the fun, everyone is welcome!
New Year’s Day Fun Run
Ring in the New Year with a fun run at Palmer’s Square Park, which is in Chicago’s beautiful Logan Square neighborhood, and enjoy some donuts and coffee afterward!
Zone 2 Book Crew Group Run - December
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
Grit Endurance Holiday Party
Join us at Midwest Coast Brewing Company (2137 W. Walnut St.), for some beers and fun with your teammates! They will also have a food popup with Five Squared Pizza! We will also be having a 🎁 White Elephant Gift Exchange! 🎄! This year, your gift (budget: $20) should represent some aspect of your favorite race — be creative, funny, and/or heartfelt! If you’d like, you’re also welcome to include a short note explaining your gift and how it connects to your favorite race. Participation is totally optioanl, but it’s highly encouraged — the more the merrier (and the more entertaining the swaps!). If you don’t have a gift, please still come!
Flip Turn 101 Swim Clinic
Join us for this 1-hour clinic that is fully focused on helping you learn the technique of flip turns! You’ll be able to get guidance and real time feedback from Grit Endurance Coaches, with plenty of time to practice during the clinic. The cost is $25, and you can register by emailing Jim @grit-endurance.com. Act quickly, because we are limiting the clinic to 12 total swimmers!
December Group Fun Run
Our December Group Run location is taking us to Streeterville! We will meet at Cupitol (455 E. Illinois) at 9am, then run for about an hour on the lakefront trail, returning back to the cafe for breakfast and coffee around 10:00! If you want to run more, feel free to knock out some miles ahead of time!
Zone 2 Book Crew Group Run - November
Are you passionate about both running and reading? Join Grit Endurance’s “Zone 2 Book Crew,” where we blend the thrill of endurance sports with the joy of literature! Each month, we’ll choose a captivating book that inspires and motivates athletes like you. At the end of the month, lace up your shoes for an easy-paced, zone 2, group run, where we’ll share insights, discuss themes, and connect with fellow runners over the pages we’ve explored.
Vision Quest Indoor Cycling - Free Trial Class #3
We’re exploring a partnership with Vision Quest where we can utilize their facility to offer in-person indoor cycling classes, using state of the art technology! Come join us on November 9, 11 or 12 for a free 1-hour class and give Coach Jim your feedback afterwards!