6 Chicago Races to Celebrate the Holidays

The Ugly Sweater Run brings a big crowd to Soldier Field to celebrate the season.
The Ugly Sweater Run brings a big crowd to Soldier Field to celebrate the season. Ugly Sweater Run
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The end of the year in Chicago isn’t exactly the busy season for running. The weather is iffy, the trails are muddy and your calendar is filled with holiday parties. But that’s not to say you have no options. In fact, the area hosts several major events around the holidays to help runners stay motivated through the gray days and dessert-filled nights. Here are six of our favorite Chicago races to add to your calendar to help get in the holiday spirit and enjoy a run in the outdoors—hopefully before the snow starts to fall.

Ugly Sweater Run

Raid the closet to find the perfect outfit for the Ugly Sweater Run.
Raid the closet to find the perfect outfit for the Ugly Sweater Run. Ugly Sweater Run

Go to the back of the closet and find that holiday sweater that you’d just assume forget for this event in downtown Chicago. The Ugly Sweater Run comes to Soldier Field on Dec. 12, with a Lakefront course and plenty of holiday cheer. You won’t be setting a PR at this 5K (as it is untimed), but you you’ll find holiday-themed aid stations at every mile serving hot chocolate and other goodies. After the race, the post-race party features Sam Adams beers and Kahlua cocktails—plus they’ll be awards for the ugliest sweater, best kids sweater, best pet attire and best mustache/beard—real or fake. All runners receive an impressive stocking cap, which will go with any sweater you get for Christmas this year.

Jingle Bell Run

You'll find a lot of runners in costume at the Jingle Bell Run.
You'll find a lot of runners in costume at the Jingle Bell Run. Courtesy of the Arthritis Foundation

The Jingle Bell Run , which raises money for the Arthritis Foundation, takes place at the Peggy Notebaert Nature Museum on Chicago’s North Side. It will be one of the louder runs you ever do, as all participants receive jingle bells to put on their shoes. Holiday costumes are encouraged, and runners can choose from a 5K or 10K course, both of which feature a Lakefront course in Lincoln Park. All participants receive a long-sleeve T-shirt and a finisher’s medals—plus awards are given three deep in all age groups. Strollers are allowed, and a 100-yard kids dash with Santa is also available for the youngsters. A second Jingle Bell run is held on Sunday, Dec. 13, in Kankakee, Ill.

Rudolph Ramble 8K

Runners receive beanie-style caps at the Rudolph Ramble.
Runners receive beanie-style caps at the Rudolph Ramble. Fleet Feet Sports Chicago

Fleet Feet Chicago hosts its annual holiday celebration on Dec. 13 with this 8K run that benefits the Ann & Robert H. Lurie Children’s Hospital. While this is probably the most competitive of the holiday races, it also focuses on the cheer, with holiday music, food and photos with Santa after the race. Toys will also be collected during packet pickup and on race day to donate to children at the hospital. This year all runners will receive beanie-style stocking caps, and Do-Rite Doughnuts and coffee are provided after the race. Holiday carolers will be entertaining on the course, and the Donner Dash is available for kids 2-12 who want to participate.

Commitment Day

Life Time Fitness organizes the Commitment Day 5K at four locations around Chicago.
Life Time Fitness organizes the Commitment Day 5K at four locations around Chicago. Life Time Fitness

Life Time Fitness created this New Year’s Day run series to encourage people to start the year off right and encourage them to think about their athletic goals for the year. Organized around their health clubs, the Commitment Day 5K runs are untimed and designed to encourage anyone to start running. In the Chicago area, choose from events in Bloomingdale, Orland Park, Romeoville and Warrenville.

New Year’s Day 5K

The New Year's Day 5K has become a Chicago tradition on January 1.
The New Year's Day 5K has become a Chicago tradition on January 1. Chicago Special Event Management

This Chicago tradition celebrates its 31 st  running on New Year’s Day when more than 1,500 runners will take to Lincoln Park to kick off the New Year. The New Year’s Day 5K features an 11 a.m. start time that is friendly for those who like to stay out late on New Year’s Eve. For those who aren’t finished ringing in the New Year, a post-race party at a local bar will continue the festivities with a free drink, raffle prizes and awards to the age-group winners. A portion of the proceeds of the event benefits the Central Lakeview Merchants Association.

Frozen Cannoli Run

Start the New Year with a friend at the Frozen Cannoli Run , a two-person race in Woodstock, IL, on Jan. 1. Two teammates share one bike between them—one rides the bike while the other runs—and switch at exchange points along the course with additional obstacles. The 5K race ends with a ride together on a sled (which will be provided), down a hill to the finish line. Most of the course is on paved trails, but mountain bikes are still recommended. Celebrate after the race with hot chocolate and, of course, cannolis.

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