What to Pack for a Chicago Weekend: Winter

Gift Ideas for the Classy Dad

Chicago winters can be brutal, but the city is still beautiful in the chilliest months of the year.

Here’s what you should pack for a trip to Chicago in the winter:

For Exploring During the Day

Snow boots. Make sure they’re comfortable for walking.


Long socks. Anything to help fight the cold, especially when there is snow on the ground.

Opt for jeans instead of leggings, especially when the temp drops at night. Or find some fleece-lined leggings.

Hats, gloves and a scarf. Don’t underestimate the brutal lake winds.


Sweaters, maybe paired with a collared shirt to keep you warmer. We’re all about layering *fashionably* to keep the cold at bay. Opting for a vest under your coat won’t hurt either.


A warm coat. Make sure to bring a coat that can withstand the wind and low temps. A coat with a hood is preferable!

For Going Out

Chicago bars lean more on the fancy side (especially downtown and the North side). Wanting to go out and look good, but also not freezing between getting in your Uber/walking between bars is a hard balance to obtain. For that, I suggest a jumpsuit with heels, or a long-sleeved dress, tights, and boots/heels.


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