Flight delays and cancellations are of course more common in the winter months.  However, they can happen anytime.  The key in handling a flight delay or cancellation is to be prepared.  On The Traveling Professor's recent small group tours to Iceland, all of our planning was put into play to make sure of a smooth trip despite several flight cancellations and extensive delays. 

Here is a strategy to follow in case of flight cancellations or delays:

Purchase Airline Tickets Directly From the Airline:  DO NOT purchase from secondary on-line sellers like Expedia, Orbitz, Kayak, etc.  In case of a flight delay or cancellation, airlines may take care of you last, if at all.  But those who booked directly with the airline are in almost all cases, handled first. In fact, some airlines will defer the handling of cancellations and delays back to the on-line booking agent, adding another frustrating level of bureaucracy to deal with.

Sign up for Travel Alerts When Booking:  Most airlines will send notifications of flight delays by text message, emails, or phone calls if that service is opted for when purchasing tickets.  Be the first to know if a flight is delayed or cancelled.

Arrange for Lodging Immediately:  If your flight is cancelled or delayed, probably everyone else's flight is cancelled or delayed.  That means the rush will be on to get lodging.  Get lodging IMMEDIATELY or risk sleeping in a lobby or on a couch.  On our recent small group tour to Iceland, we have standing instructions in to our hotel to book our customers first into our Reykjavik hotel if flights were delayed or cancelled - and it worked.  We don't want anyone sleeping on the floor or on a couch.

Call the Airline Right After Booking Lodging:  Although some airlines re-book immediately, if you purchased the ticket directly from them, but sometimes they don't.   Get on the phone with the airline immediately, have flight documents including record locator, be prepared to wait, and have airlines book you on the next available flight.

Have Trip Delay/Cancellation Insurance:   On my way to the Boston airport, I received the message that my 8 pm flight that night was re-scheduled to early the next morning.  It was too late to go back home and if I did, I didn't want to get up at 4 a.m. the next morning to fly out.  However, since I had trip delay insurance (free, with my credit card) I booked a hotel at $260 per night at the airport, had dinner ($80 for two) and will be reimbursed with my trip delay insurance (trip delay insurance is sometimes called trip interruption insurance).