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Set up google flight tracker alerts for a r.t. flight through Prague, Budapest, Berlin, or Frankfurt. My guess is summer would be a good time to book for winter travel. Booking too early will get you average fares, not deals.
I’ve found great fares on Turkish Air (star alliance) to Frankfurt. Once in EU can book flights (like on Ryanair, Easyjet, Eurowings) or trains locally - can get around for under $100 per leg.
Also TAP (Portugal) and Play (Iceland) airlines can also have great deals from US.
I’d bring a warm coat and boots and a mini full spectrum lamp to reset time change. The Christmas markets can be cold and it gets dark at like 3:30.