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📅 Dec - Feb
🌡️ 2°C / -6°C
☁️ Freezing, snowy, and famously windy
Chicago winters are brutally cold and windy, requiring serious thermal preparation for business travelers. Pack insulated layers, a heavy winter coat, and waterproof boots to handle temperatures dropping below freezing and frequent snow. The Windy City's notorious gusts demand wind-resistant outerwear that won't compromise your professional appearance.
Passport
Visa / entry documents
Travel insurance certificate
Flight & hotel confirmations
Driver's license
International driving permit
Credit / debit cards
Cash (local currency)
Emergency contact card
Underwear ×7
Socks ×7
Comfortable walking shoes / sneakers
Light cardigan / layer
Pyjamas / sleepwear
Casual t-shirts ×3
Jeans / trousers ×2
Belt
Thermal base layer top
Thermal base layer bottoms
Heavy winter coat
Light puffer / down jacket
Fleece pullover
Wool hat / beanie
Gloves / mittens
Scarf
Wool / thermal socks ×5
Waterproof winter boots
Waterproof trousers
Business suit / blazer
Dress shirts ×3
Dress trousers / skirt
Formal shoes
Tie / pocket square
Toothbrush + toothpaste
Shampoo + conditioner
Body wash / soap
Deodorant
Razor / shaving supplies
Moisturiser
Lip balm
Hair brush / comb
Nail clippers
Heavy-duty lip balm
Thick hand cream
Prescription medications
Pain relief — ibuprofen / paracetamol
Antihistamines
First aid kit
Band-aids / plasters
Antiseptic cream
Motion sickness tablets
Eye drops
Smartphone + charger
Universal power adapter
Portable battery pack
Headphones / earbuds
Camera + charger + memory cards
Laptop + charger
Daypack / backpack 20L
Packing cubes
Luggage lock
Luggage tags
Reusable water bottle
Travel pillow (neck)
Eye mask + earplugs
Money belt / hidden wallet
Sunglasses
Reusable tote bag
Compact umbrella
Planning your Chicago itinerary? Browse our free 3-day Chicago itinerary to see the full day-by-day plan. You can also use our free collaborative travel itinerary planner to build, map, and share your own custom trip.