Trail races near Chicago (2026-27)
Updated
11 trail races are coming up near Chicago in the next 90 days; the next is Outlast Chicago on Saturday, October 24 in Palatine. 20 trail races are listed near Chicago for the next 12 months; the next one starts from $100.
All ChicagoChicago (city) (1)North Shore & North Suburbs (6)West Suburbs (7)South Suburbs (5)Northwest Indiana (1)
By date
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from $100Goes up Oct 22
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Run for Your Life Race at Robinson Lake - 5K and Haunted Fun Walk/Run
Sat Oct 24 · 6:00 PM · Hobart · Northwest Indiana
1 mile5KTrail
from $25 -
from $25Goes up Oct 20
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The Forge Trail Run Festival
Sat Nov 14 · 7:15 AM · Lemont · South Suburbs
10KHalf marathon18.6 miles37.2 milesTrail
from $62.50Goes up Oct 25 -
The Universal Sole November Trail Challenge
Sat Nov 21 · 10:00 AM · Willow Springs · South Suburbs
4 miles8 milesTrail
from $50Goes up Nov 1 -
from $35Goes up Nov 12
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from $39.99Goes up Nov 7
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Cancelled Holiday Cross Country Race & Reunion
Sun Nov 29 · 10:00 AM · Evanston · North Shore & North Suburbs
3.62 milesTrail
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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
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from $60Goes up Jan 30
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Fox Valley Winter Challenge Trail Series 10K
Sun Mar 14 · 10:00 AM · St. Charles · West Suburbs
10KTrail
from $70Reg. closed -
from $25Reg. closed
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F^3 Cap Sauers Trail Marathon & 10 Mile
Sat May 8 · 7:30 AM · Palos Hills · South Suburbs
10 milesMarathonTrail
from $75Goes up Nov 9 -
Oneness 10K Run and 5K Run/Walk
Sat Jun 5 · 7:20 AM · Palatine · North Shore & North Suburbs
5K10KTrail
from $31.50Goes up Jan 5 -
Naperville Trails Half Marathon & 10K
Sat Sep 11 · 8:00 AM · Wheaton · West Suburbs
10KHalf marathonTrail
from $54.99Reg. closed
Quick answers
How many trail races are near Chicago in the next 3 months?
11 trail races are listed near Chicago between October 17 and January 15. The next is Outlast Chicago on Saturday, October 24 in Palatine.
What is the cheapest trail race near Chicago right now?
Run for Your Life Race at Robinson Lake - 5K and Haunted Fun Walk/Run on October 24 has the lowest listed entry fee in the next 90 days: $25. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Chicago?
Fast Track Cross Country Open: the 5K goes from $25 to $29 after October 20. 11 more of these trail races publish a later price increase.
Are there trail races near Chicago this weekend?
None are listed for October 17 to October 18. The next is Outlast Chicago on Saturday, October 24 in Palatine.