Cupid's Undie Run - Chicago

Chicago, Illinois, United States

Feb, 2027 (TBD)

Fun Run, Fundraiser

Race Information

This February be a part of something great. There are fewer things in this world that feel better than getting half naked for charity. Cupid's Undie Run lets you live that dream in the winter, in Chicago. 

The run itself happens around Valentine's weekend each year and is a “brief” fun run that takes place in the middle of a BIG party. That’s right: party, run (a mile-ish, at your own pace), party – all to find a cure for neurofibromatosis (NF), a genetic disorder that causes tumors to grow on nerves throughout the body and affects 1 in every 3,000 births.

Be a part of something great. Last year Cupid’s raised over $3.5 Million to #EndNF and they’re relying on YOU to join and make this year’s fundraising the biggest and best yet. Start a team, join a team, or just run solo and make some new friends!

Destination Run Pick of the Month - La Jolla Half Marathon, 10K and 5K 

Get ready for San Diego’s most picturesque and beautiful point-to-point races - La Jolla Half Marathon, 10K and 5k, taking place on May 16, 2026.

Use code RGCC18 to SAVE 18% on your race entry!

Whether you choose the Half Marathon, 10K or the 5K, the course gives you the best of Southern California: sweeping ocean views, cliffs that make you look twice, and that iconic stretch through Torrey Pines where the landscape opens up and reminds you why you love to run.

The finish line isn’t just a destination; it’s a celebration! Enjoy the vibrant festival atmosphere filled with music, delicious food, and vendors showcasing the latest running gear. Relax with complimentary recovery options like massages, cold plunges, TENS units, and massage chairs.

Every runner gets a finisher’s medal, race shirt, tote bag, food bag, and free race photos, so you can keep every smile, stride, and moment of victory.

Discover what makes running in San Diego truly special—register today!

Get Event Info

 

Get a Training Plan for this Run

Receive 2 FREE Weeks of personalised run training from our friends at Runna

The Runna app, the ultimate running coach in your pocket, gives you personalised programs that sync with your favourite devices, includes strength and mobility training, and offers complete support.

You get 2 weeks for free!

Learn more about Runna. Click the link below.

Check Out Runna

Race Facts

Race Size: 500 - 1,000

Course Type: Road

Boston Qualifier: No

Kids Run: No

Where to Stay

Use this map to find hotels and airbnb accommodation near this race location.