Congrats!
Best way to transfer money is by talking to your bank. I transferred a considerable amount and used a service called Money2World from my bank itself. Most large banks have such services. Will be more helpful if you look at options based on your country itself. I am from India, so I used Money2World from HDFC. Also, countries have taxation and other issues too, so make sure you check everything in detail as well. You can also carry upto $10k in cash in total(for entire family). I had to sort out 20% tax-withholding and other things too - so a good idea to sort these things out asap.
For flights - best if you look based on routes. I was flying to Calgary from India, so decided to use KLM as it was the best airline that lands and as I prefer to flying domestic airliners anywhere. If you can tell us which country you'll be flying from, that'd be a great start!