Living in Chicago means enjoying many fun, exciting, and unique things that set us apart from other cities. From Wrigley Field and The Bean to the beautiful shoreline of Lake Michigan, there’s always something iconic to experience. But Chicago also comes with challenges — especially the weather, which stays freezing for about 4–5 months of the year. In this article, I’ll share options for late-night fun without the fear of frostbite, whether you’re exploring the city by day or heading out to clubs and restaurants at night. Year-round and round the clock, these solutions will help keep you warm from head to toe.
Warm Up Without Over-Layering
For anyone who likes to stay warm without bulky layering, here’s my go-to insulation solution. Warm drinks and hearty meals can actually help boost your body temperature significantly. A hot meal with rich ingredients and healthy fats fuels your metabolism — and burning that energy helps generate heat internally. There’s nothing like a hot drink on a cold day to warm your cheeks and thaw you from the inside out. This combination can save you from the chill from December through March. And who says hot chocolate is only for Christmas? Rock hot chocolate, apple cider, and hot tea in both hands all winter long for a little break from the cold.
Another pocket-sized solution I use all the time to fight cold hands is hand warmers. I carry them everywhere — they easily fit in a winter coat or jeans pocket and are super versatile. Just shake them up for maximum heat and pack them in your bag or coat for instant warmth.
Layering & Clothing Essentials
For those who do like layering, there are great options that are both practical and stylish. Fleece-lined leggings, thermal tights, gloves, mittens, and warm socks make a huge difference and often aren’t visible under most outfits. Many local Chicagoans also recommend base layers like merino wool or moisture-wicking fabrics rather than cotton, since cotton holds moisture and can make you colder.
Brands people love for winter layering range from outdoor performance names to everyday comfort pieces — thermal leggings and base layers. Options like Uniqlo’s Heattech or Under Armour ColdGear leggings are lightweight yet warm while still fitting under your regular clothes.
When it comes to outerwear, waterproof and wind-resistant pieces are key. Snow and wind can sap heat quickly, so waterproof layers and boots with good traction help keep you dry and warm. Many locals swear by sturdy boots from brands like Blundstones, Columbia, and The North Face for winter performance, which really come in handy navigating Chicago sidewalks in snow and ice.
Accessories That Make a Big Difference
Let’s talk accessories — they really tie everything together. Warm winter accessories aren’t just cute, they’re necessary. Furry hats (yes, the Instagram-famous ones) will be lifesavers in the cold. Earmuffs are another great ear-covering option, and on rare sporty occasions, a fleece-lined headband is perfect for runs or quick walks. Scarves are the most versatile accessory — whether satin, chunky knit, wool, or cashmere — they add warmth and style to any outfit.
Stay Active & Enjoy the City
A simple yet effective way to fight the cold all day long is to stay moving. On especially chilly days, I bundle up and walk from shop to shop or café hop around the city. Walking keeps me active and warm — and ducking into cozy indoor spots for a warm drink or snack is a great way to take a break from the cold while still enjoying Chicago.
Chicago’s winter doesn’t have to derail your plans. There are amazing winter activities — from ice skating at Millennium Park’s ice rink to cozy heated igloos and rooftop winter bars where you can sip warm drinks and enjoy skyline views — that make the season memorable and fun.
Final Thought
Hopefully these tips and tricks don’t just help you stay warm this seemingly never-ending winter — maybe they’ll help you look forward to it, or at least appreciate the summer that much more!