Chicago Winter Running Tips
Readers & runners in Bronzeville in the winter.
by Allison Yates
We’re all about exploring Chicago at Read & Run Chicago—and that means Chicago in every season. Rain or shine, snow or sleet—our book-themed guided run programming will still happen.
Our events are not your typical training runs—you’re joining fellow readers & runners to a new-to-you Chicago neighborhood to bring a book to life on a tour, and that means stopping along the way at real-life places from the inspiring book.
[Related: Guide to Chicago Running 2025]
So what should you wear to a Read & Run Chicago event when the temps drop and winter takes over the Windy City?
Here’s your go-to Chicago winter running guide.
Dress in Layers
Winter in Chicago can be unpredictable—temps can feel far colder than the thermostat reads, especially when you’re moving then pausing. For Read & Run Chicago event, where we stop along the way rather than sprint straight through, layering is essential.
Here are some tried and true tips:
Wear a base layer: Choose a moisture-wicking long-sleeve shirt (synthetic or merino wool) that keeps sweat away from your body.
Mid layer: Wear a vest to keep your core warm or thin windbreaker. Avoid a bulky puffer—remember, your body temperature will increase significantly once you start moving, and you don’t want to trap all that sweat underneath to chill you down when we stop!
Extra outer layer for stops: We know the Chicago winds can bite—and sometimes, they attack right at a pivotal moment one of our book-themed routes! If you wear a vest as your mid layer, consider also bringing another thin windbreaker to take on and off while you’re stopped.
Bottoms: Thermal running tights (with pockets) are ideal.
Accessories: Bring a hat or headband, gloves (preferably touchscreen-friendly so you can snap photos), and a lightweight buff or neck gaiter for wind and exposed skin (this also doubles as a handkerchief for the inevitable sniffles…)
Why this matters: Unlike a training run where you might keep a steady pace and stay warm, during our tours you’ll stop along the way at relevant book-themed points of interest, take photos, and talk about the book and neighborhood. Those pauses make you more susceptible to chilling—so layering is your friend.
Allison and Tahnee at a Peace Runners 773 group run at our Support a Run Club visit in early 2025. Credit: Andre Warren Photo.
Pick Waterproof Shoes & Socks
Shoes: Choose your trusted running shoes that handle urban terrain (sidewalks, mixed pavement, maybe a bit of gravel on trail runs). A slip-proof tread is always helpful in Chicago!
Socks: Consider thicker running socks or merino wool blends to keep your feet warm—but not too bulky, as you don’t want your shoes to feel tight. If there’s snow or slush, you might even pick socks that are water resistant.
Traction: If ice is likely or weather is slushy, you might bring slip-ons or micro-spikes you can strap on at stops—but only if you’re comfortable with them. Most readers & runners have not had to use these.
Stay Visible
Winter doesn’t just means cold—it also means dark! With our weeknight events usually happening at 6:00 PM and later, this means we’re fully in the dark from the start. Here’s how to stay most safe in these conditions:
Wear clothes with reflective details or neon colors
Wear a light-up vest or arm bands
Bring a lightweight running belt / small backpack with essentials: phone (for photos and emergency contact), a small snack, a layer you can dump if you warm up, and maybe a bottle of water
Try These Practical Tips
Post-run change of clothes: After the tour ends, you’ll likely cool down faster—and get chilly if you’re sitting in sweaty clothes. Though we have perfected the art of the “sweaty author talk”—that doesn’t mean it’s the most pleasant. Bring a change of clothes for the post-run portion to make sure you can fully embrace the author talk or discussion.
Hydration & nutrition: Even in cold weather you sweat and burn calories. We always give you a bite to eat and hydration after the running route, but if you think it would be helpful for you, consider also bring a drink and snacks for during the route.
Readers & runners in Hyde Park in February 2025 during our Book Club Run of Becoming.
Sample Outfit for a Winter Read & Run Chicago event
Here’s a quick “what I’m wearing” sample list for a typical winter event:
Base: Long-sleeve synthetic or merino shirt
Mid: Vest
Extra outer: Bright wind/water-resistant running shell with reflective trims
Bottoms: Black insulated running tights
Shoes: Your usual road running shoes with good tread
Accessories: Running headband, lightweight running gloves (touchscreen-friendly), neck gaiter
(Optional) Bag: Small running belt or backpack for an extra layer
Visibility: Reflective vest
Readers & runners run through snow in Pilsen in 2022.
Since we at Read & Run Chicago design our programming as guided running tours—not just training runs—you’ll be moving and stopping, exploring, chatting, reading, pausing for views, and then running again. That means your outfit needs to handle both motion and moments of stillness in winter conditions.
By layering smartly, choosing weather-appropriate gear, and staying visible and ready, you’ll be fully prepared to explore Chicago using movement and stories with us, and keep feeling proud to be a Chicagoan.
See you running around, readers & runners—hopefully bundled up, with your curiosity, and ready to take on winter running!