How to Bike Through Winter (My Real Tips After 15 Chicago Winters)

Winter bike commuting isn't easy, but after fifteen years of cycling through Chicago's snow, slush, and below-zero days, I've learned what actually works. This video breaks down the exact winter bicycle commuting tips, strategies, and bike winter gear that help you stay warm, stay upright, and enjoy snow cycling.

I cover mindset, temperature rules, bike handling in snow, and complete cold weather cycling clothing breakdown: hands and feet protection, face and head gear, core layers, and leg protection. You'll also get practical winter bike commuting extra tips like pogies, toe caps, fenders, winter-specific bags, visibility gear, and simple tricks that make cold-weather cycling safer and more fun.

Whether you're preparing for your first winter commute or improving your snow cycling setup, these are the real lessons from fifteen Chicago winters on a bike.

If you enjoy videos that mix practical cycling advice with real ride atmosphere, check out my fall riding video and gear playlist in the end screen.

Chapters:
0:00 – Mindset: Why Winter Riding Feels Better Than You’d Think
1:08 – Snow Riding: Handling and What Nobody Told Me My First Winter
3:03 – Temperature Rules: 10 Degrees Changes Everything

3:39 – Clothing Overview: How to Actually Stay Warm
3:45 – Hands
4:56 – Toes & Feet
5:42 – Face Protection
7:33 – Head & Helmets
8:04 – Core Layers
9:42 – Leg & Lower Body Warmth

10:28 – Extra Tips That Make Winter Biking Work
12:05 – Watch Next: Chicago’s Lake Shore (9 Incredible Spots)


'WINTER BIKE RIDE – FULL AFFILIATE GEAR LIST

BIKE SETUP
• Front Bike Rack – https://amzn.to/49WOEr9
• Fenders – https://amzn.to/49W6zhD
• Nitecore Rear Light – https://amzn.to/4i4StfV
• Fenix Bike Light / Headlamp – https://amzn.to/3K243Mi
• Bell – https://amzn.to/3LLS1qQ
• EVOC Bike Hip Pack – https://amzn.to/49UmhK4
• KOROS DURUS GPS – https://amzn.to/4nUnFzJ
• Phone Mount – https://amzn.to/4oPgZV8

HANDS + FEET
• Merino Wool Gloves – https://amzn.to/3WVMsIX
• Bar Mitts / Pogies – https://amzn.to/4oFSzNr
• Neoprene Toe Caps – https://amzn.to/4i2vwtG
• Shower Pass Foot Booties – https://amzn.to/4pbwmGZ

FACE
• Merino Wool Buff / Neck Gaiter – https://amzn.to/44dNF21
• Neoprene Face Mask – https://amzn.to/4pi2EjU
• Dermatone Skiing Face Balm – https://amzn.to/4r7RQqg

HEAD
• Black Skullcap / Winter Cycling Cap – https://amzn.to/49nBWS3

CORE + LAYERS
• Merino Wool Long Johns / Base Layer Bottom – https://amzn.to/43yHCVB

CAMERA + AUDIO GEAR
• Action Cam – https://amzn.to/3XxDIJ4
• Main Camera (Osmo Pocket 3) – https://amzn.to/3JD9gdv
• Drone – https://amzn.to/3XwqPip
• DJI Mic – https://amzn.to/3WZAKNh

AFFILIATE DISCLAIMER
Some of the links above are affiliate links, which help support the channel at no extra cost to you. Thanks for riding along.