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Winter races near Chicago (2026-27)

Updated October 17, 2026

36 races are on the calendar near Chicago in winter 2026-27, starting with Crete Country Christmas 5k Grinch Run on Saturday, December 5 in Crete. That covers December to February. 18 of them publish an upcoming price increase, so signing up early saves money.

All winter races 5K races (33)10K races (18)Half marathons (15)Trail races (6)

By date

Crete Country Christmas 5k Grinch Run

Sat Dec 5 · 8:00 AM · Crete · South Suburbs

5K

from $25Goes up Nov 28
Santa Hustle Chicago

Sat Dec 5 · 8:00 AM · Chicago · Chicago (city)

1K5K10K

from $29.99Goes up Nov 1
Reindeer Run 5K

Sat Dec 5 · 8:30 AM · Wheaton · West Suburbs

5K

from $35Goes up Nov 5
Rotary Santa Run Walk & Reindeer Dash

Sat Dec 5 · 9:30 AM · Arlington Heights · North Shore & North Suburbs

5K

from $45Goes up Nov 1
The Village of Norridge 5K Reindeer Run and Kids Dash

Sat Dec 5 · 9:30 AM · Norridge · Chicago (city)

5K

from $40Goes up Nov 27
Santa's Run through the Lights 5K Run/Walk

Sat Dec 5 · 8:15 PM · Geneva · West Suburbs

5K

from $12.99
Lemont Frigid 5K

Sun Dec 6 · 8:00 AM · Lemont · South Suburbs

5K

from $45Goes up Nov 19
Jingle Bell Run - Chicago, IL

Sat Dec 12 · 7:30 AM · Chicago · Chicago (city)

1 mile5K

from $40Goes up Nov 1
Run for Breast Cancer 5K/10K/13.1 Chicago/Evanston

Sat Dec 12 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Sunrise Marathon 5K/10K/13.1 Chicago/Evanston

Sat Dec 12 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog

Sat Dec 12 · 8:00 AM · Park Ridge · North Shore & North Suburbs

5KTrail

from $45
Candy Cane Course - Greater Chicago

Sat Dec 12 · 9:00 AM · Elk Grove Village · North Shore & North Suburbs

1 mile5K10K9.3 miles

from $27Goes up Oct 19
Single & Mingle Spirits Run Christmas Style 5k

Sat Dec 12 · 10:00 AM · Warrenville · West Suburbs

5K

from $45Goes up Nov 17
The Universal Sole December Trail Challenge

Sat Dec 12 · 10:00 AM · Chicago · Chicago (city)

4.5 milesTrail

from $50Goes up Nov 1
Festivus 5K Run

Sun Dec 13 · 8:10 AM · Chesterton · Northwest Indiana

1K5K

from $10Goes up Nov 21
Santa Run & Walk 5K/2K | Hometown Happenings

Sat Dec 19 · 8:00 AM · Crown Point · Northwest Indiana

5K

from $30
Catch the Elf 5k & 10k

Sat Dec 19 · 9:00 AM · Markham · South Suburbs

5K10K

from $35Goes up Dec 5
A Merry Christmas Run 5K/10K/13.1 Chicago/Evanston

Sat Dec 26 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
New Year's Run 5K/10K/13.1 Chicago/Evanston

Sat Dec 26 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Cheers to New Year's 5k Run/Walk

Fri Jan 1 · 10:00 AM · Itasca · West Suburbs

5K

from $30Goes up Nov 20
Resolution Run 6K

Fri Jan 1 · 11:00 AM · Olympia Fields · South Suburbs

6KTrail

from $40Goes up Dec 14
Time Travel Half-Marathon/5K/10K - Greater Chicago

Sat Jan 2 · 9:00 AM · Greater Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $22Goes up Nov 9
MLK Jr. Freedom Run 5K/10K/13.1 Chicago/Evanston

Sat Jan 16 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Sunrise Marathon 5K/10K/13.1 Chicago/Evanston

Sat Jan 16 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Fox Valley Winter Challenge Trail Series 5K

Sat Jan 23 · 10:00 AM · Batavia · West Suburbs

5KTrail

from $60Reg. closed
Fox Valley Winter Challenge Trail Series 5k/8k/10k

Sat Jan 23 · 10:00 AM · Batavia · West Suburbs

5KTrail

from $40Goes up Dec 12
Coffee Lover Run Chicago/Evanston

Sat Jan 30 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Run for Donut Chicago/Evanston

Sat Jan 30 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
18th Annual F^3 Lake Half Marathon & 5k

Sat Jan 30 · 10:01 AM · Chicago · Chicago (city)

5KHalf marathon

from $59Goes up Oct 26
Run for Chocolate 5K/10K/13.1 Chicago/Evanston

Sat Feb 13 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Valentine's Day Run 5K/10K/13.1 Chicago/Evanston

Sat Feb 13 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Donut Dash 10K/5K/2K | Hometown Happenings

Sat Feb 20 · 7:45 AM · Crown Point · Northwest Indiana

1.25 miles5K10K

from $25Reg. closed
Fox Valley Winter Challenge Trail Series 8K

Sat Feb 20 · 10:00 AM · Aurora · West Suburbs

8KTrail

from $65Reg. closed
Run For Mental Health Chicago/Evanston

Sat Feb 27 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Run Together Against Breast Cancer Chicago/Evanston

Sat Feb 27 · 7:30 AM · Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $30
Time to Paddy 5K/10K & Lucky 13.1 - Greater Chicago

Sat Feb 27 · 9:00 AM · Greater Chicago · Chicago (city)

1 mile5K10KHalf marathon

from $22Goes up Nov 2

Other seasons near Chicago

Quick answers

How many races are near Chicago in winter 2026-27?

36 races are listed near Chicago in winter 2026-27. The first is Crete Country Christmas 5k Grinch Run on Saturday, December 5 in Crete, and the last is Time to Paddy 5K/10K & Lucky 13.1 - Greater Chicago on February 27.

What is the cheapest race near Chicago in winter 2026-27?

Festivus 5K Run on December 13 has the lowest listed entry fee: $10. Prices are before the registration platform's processing fee.

When does the next early-bird price end for races near Chicago?

Candy Cane Course - Greater Chicago: the 5K goes from $38 to $42 after October 19. 17 more of these races publish a later price increase.

Are there half marathons or marathons near Chicago in winter 2026-27?

Yes: 15 half marathons and 0 marathons. The first is Run for Breast Cancer 5K/10K/13.1 Chicago/Evanston on December 12.