With another Chicago Marathon behind us and Old Man Winter threatening to lock us inside soon, many of us wonder how we’re going to make it through the next few months without lacing up our sneakers and heading outside. Fortunately, the holidays offer up plenty of opportunities for a fun run, whether it’s as part of one of Chicago’s many laid-back Turkey Trots or a more serious half-marathon. So get to one of the city’s best running shops, gear up and go. Here are our picks for the best fun runs this fall and winter, starting with this weekend.
Monster Dash: Join the ghosts, zombies, witches and werewolves at this Halloween running event. Sign up for the 5K, 10K or half-marathon. This race isn't just about personal records, though. You're also competing in a costume contest. (Grant Park, Oct 31, 9am. $49.99–$79.99)
Hot Chocolate 5K/15K: Taste sweet victory, whether you run the 5K or the full 15 kilometers. Sweat it out and satisfy your sweet tooth, as the post-race party is waiting with a fantastic fondue. (Grant Park, Nov 8, 7am. $54–$79)
Chicago's Perfect 10: Enjoy the breeze along the lake as you hit the trail, whether you want to run 10 miles or 10 kilometers. This mid-November race is the perfect way to take advantage of the fall before cabin fever sets in. (Navy Pier, 600 E Grand Ave, Nov 14, 7:30am. $51–$68)
Santa Hustle 5K: Don't be surprised when you see hundreds of Santas running through Chicago in early December. Every participant in this festive footrace will receive a free Santa hat, beard and half-zip to wear while running. You can expect plenty of cookies, candy, Christmas music and even an after-party at this event, which benefits the American Cancer Society. (Soldier Field, 1410 Museum Campus Drive, Dec 5, 9am. $45 in advance)
Ugly Sweater Run: You've heard of ugly runners, but this takes bad form to a whole other level. Put on your itchiest, most awful holiday sweater and race to the finish line. No complaining—the race ends with a Kahlua cocktail or a beer. (Soldier Field, 1410 Museum Campus Drive, Dec 12, 11 am. $40)
New Year's Day 5K Run/Walk: Here's to starting off 2016 on the right foot. I mean, you may as well head out for a lakefront run. Isn't "get more exercise" on everyone's list of New Year's resolutions? (Lincoln Park Conservatory, 2391 N Stockton Drive, 11am. $20.16–$50)
Cupid's Undie Run: Fine. If you really want to run through Wrigleyville in your underwear, you can. But just for today, and only because it also benefits the Children's Tumor Foundation. Festivities begin at noon, and the race starts at 2pm. Happy almost Valentine's Day! (John Barleycorn, 3524 N Clark St, Feb 13, noon. $30–$55)