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With the possible exception of very routine travel, you should seriously consider travel insurance. The cost may be determined by your total trip cost and duration, the age of travellers, level of coverage requested for certain problems (eg: costs of treating sickness or injury, or medical evacuation), and coverage for domestic versus international travel. Many insurance sources will cover pre-existing medical conditions if the insurance is purchased within a very few days of booking your trip; they may not if bought later.
Airline insurance purchased at the time you purchase your ticket may only focus only on the airline's responsibilities, while a quality policy will cover your end-to-end trip. You may obtain better rates by buying a policy through or from an association you belong to, eg: AAA, AA, AARP. Very-frequent travellers should consider long-term (annual) policies; coverage can be equivalent while costing much less per trip.