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Winter trail races near Chicago (2026-27)
Updated
6 trail races are on the calendar near Chicago in winter 2026-27, starting with Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog on Saturday, December 12 in Park Ridge. That covers December to February. 3 of them publish an upcoming price increase, so signing up early saves money.
All winter races5K races (33)10K races (18)Half marathons (15)Trail races (6)
By date
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Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog
Sat Dec 12 · 8:00 AM · Park Ridge · North Shore & North Suburbs
5KTrail
from $45 -
The Universal Sole December Trail Challenge
Sat Dec 12 · 10:00 AM · Chicago · Chicago (city)
4.5 milesTrail
from $50Goes up Nov 1 -
from $40Goes up Dec 14
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from $60Reg. closed
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Fox Valley Winter Challenge Trail Series 5k/8k/10k
Sat Jan 23 · 10:00 AM · Batavia · West Suburbs
5KTrail
from $40Goes up Dec 12 -
from $65Reg. closed
Other seasons near Chicago
Quick answers
How many trail races are near Chicago in winter 2026-27?
6 trail races are listed near Chicago in winter 2026-27. The first is Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog on Saturday, December 12 in Park Ridge, and the last is Fox Valley Winter Challenge Trail Series 8K on February 20.
What is the cheapest trail race near Chicago in winter 2026-27?
Resolution Run 6K on January 1 has the lowest listed entry fee: $40. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Chicago?
The Universal Sole December Trail Challenge: the 4.5 miles goes from $50 to $55 after November 1. 2 more of these trail races publish a later price increase.
Are there half marathons or marathons near Chicago in winter 2026-27?
No half marathons or marathons are listed near Chicago in winter 2026-27 yet.