Generated from your trip description + your profile
Packing List — Chicago
⚠️ Don't-forget flags — you've left these behind before
Phone charging cable
Sunglasses
Nail clippers
Lip balm / chapstick
Pulled straight from your profile's always-forgets. They're also repeated in their real categories below.
🧾 Documents & money
- Driver's license / ID + a backup card photo on your phone
- Two payment cards + a little cash for tips
- Conference badge confirmation (screenshot + printed)
- Hotel + client-dinner reservation confirmations
👕 Clothing scaled to 5 days · merino/quick-dry so pieces re-wear
- 2 smart-casual outfits for the conference floor (mix-and-match tops + one pair of chinos)
- 1 dressier outfit for the client dinner
- 3 merino tees / base layers (re-worn across days)
- 1 pair jeans + 1 pair chinos
- 5 pairs underwear · 3 pairs merino socks · sleepwear
🧥 Layers & outerwear you run cold → an extra layer, plus lake wind & rain
- Warm midlayer (fleece or light down) — your cold-bias non-negotiable
- Packable rain shell (~40% rain midweek, gusty off Lake Michigan)
- Knit hat + light gloves for the walk between venues
👟 Footwear
- Comfortable waterproof walking shoes (downtown is walkable, wet pavement)
- 1 dressier pair for the client dinner
🧴 Toiletries & health
- Grab your pre-packed TSA travel kit — one item, already compliant (don't re-itemize)
- Lip balm / chapstick (dry cold + plane air)
- Any daily meds + a small pain-reliever
- Nail clippers
🔌 Electronics domestic, same plug — no adapter needed
- Phone + charging cable + wall plug
- Portable battery pack (always-brings)
- Noise-cancelling earbuds (always-brings)
- Sunglasses (bright off snow/glass, even in March)
💼 Work travel kit
- Laptop + charger
- USB-C → HDMI dongle + a spare USB-C cable
- Slide clicker / presenter remote
- Business cards (restock the case)
- Branded notebook + two pens
Folded in from your OP's “Work travel kit” — edit it there, not here, and every work-trip list updates. Clicker + dongle ride in the daypack; nothing sharp or oversized, so it all stays carry-on.
🎒 Activity-specific
- Conference: laptop, 2 smart-casual outfits, badge, notebook
- Client dinner: the dressier outfit + a few business cards
✨ Nice-to-have / optional
- Compact travel umbrella
- Reusable water bottle (empty through security)
- Melatonin for the early flight out
Notes
- Weather came from a forecast lookup about a week out confirm — re-check a day or two before you fly; lake-effect swings fast.
- 5-day trip is under your ~6-day laundry threshold, so quantities are packed for the whole trip rather than planning a wash.
- Carry-on only: all liquids TSA-sized (your pre-packed kit already is); the slide clicker and dongle are fine in the cabin.
- Assumed the conference dress code is smart-casual confirm — swap in a blazer if it's a dressier crowd.