1. Warmer clothes? So like long sleeved shirts and pants? Jackets depending on the temperature at your destination? Are you connecting anywhere? Are those connections at like BWI or MDW where it can snow?
2. Warmer clothes based on the temperature at your destination?
3. Since it's WN, remember that they will never pay for anything, so I would recommend budgeting at least one unexpected night at a hotel into your winter travel plans (or having a bunch of hotel points in different programs works too). Also remember that LGA is essentially a WN outstation, as is BUF, SEA, etc. with few rebooking options. If you get stranded in BUF (
remember they just got literally six feet of snow), maybe a couple nights? Flying to Buffalo or NYC in the winter on WN may just cost you more than your promo companion pass saves. There's a reason WN is basically giving these away to fill planes in Jan and Feb.
4. Probably primarily indoor activities as it may (will likely) be frigid in Manhattan and NE Canada and rainy in Seattle and BC. Also it seems like you have your itineraries pretty set?
Your 2022 itineraries sound much more pleasant to me in the winter
