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flying with carry-on vs checked bags

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What's the general consensus here on whether to just do carry-on bags or to check some? We have always just done carry-on (even before airlines started charging) to speed things up getting out of the airport and so we wouldn't have any lost bags.

For our upcoming trip we're considering checking a bag or two but we're completely torn. It's a 17 day trip and it would be sooo nice to have an extra bag with a few comforts of home... favorite coffee, Hot Shot machine (instant hot water for tea, oatmeal, etc) enough clothes/boots to keep me warm, umbrella, and we could go ahead and pre-purchase a lot of the things we would have to buy there (toiletries, picnic stuff, etc) .

It's $50 to check one bag round trip, so we're considering upgrading our American Express card to the next level for $40 so all 4 of us would actually be able to check a bag for "free" (plus we'd get 10,000 bonus FF miles).

Our big concern is LOST baggage. We would still carry-on the valuables and things we couldn't do without. Our other concerns are lugging around the extra luggage and having to wait for it rather than a quick airport exit.

Checking bags also has advantages beyond being able to take extra things. For once it would be so nice for us not to have 8 bags that the 4 of us need to go through security with and then on the plane quickly stow and get out of the way.

Just looking for a push one way or the other!

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