Chicago doesn’t just test your budget or your coat collection—it tests your endurance.
Thinking about packing your bags for the Windy City in 2026? You might want to pause and check your bank account and your winter coat inventory before booking that moving truck. Chicago is a city of broad shoulders and deep-dish pizza, but it also demands a level of grit that catches many newcomers completely off guard.
From the bone-chilling gusts off Lake Michigan to the bewildering politics of parking spots in February, surviving here requires a specific set of skills and a lot of patience. If you cannot handle the intensity of urban life mixed with extreme weather and steep costs, you might find yourself regretting the move before the first snow melts.
The Brutal Wind Chill
The nickname “Windy City” might have political roots, but the actual wind coming off the lake in January is physically painful. It cuts right through your layers and makes the air temperature feel twenty degrees colder than what the weather app says.…