We recommend always keeping cigars in your carry-on bags, because an airplane cabin is climate-controlled while the cargo area is not. Humidity and temperature matter for keeping cigars at their best.
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Don't let cigars roll around in a suitcase with extra space. If you plan to smoke the cigars within a few days, they should stay in good shape if you put them in a Ziplock bag then store them in a firm container. If your trip will last more than a few days, pack your cigars in a travel humidor.
Alcohol and tobacco: Each traveler over 21 years of age may import up to one liter of alcoholic beverage and either 200 cigarettes, 50 cigars or two kilograms of smoking tobacco for personal use. Cigars may not be of Cuban origin. beverages, perfumes containing alcohol with a retail value of more than $5 or cigarettes.
You can try. But they will be visible on an x-ray scanner, and, unless you hide them really well amidst other organic matter, they will be even quite distinct, as are cigarettes, for that matter.
Wet an unused kitchen sponge with distilled water and place in a clean zip-seal bag along with your cigars and zip it closed. Monitoring the humidity level won't be an exact science with this method – without the hydrometer the humidor provides – but it is a simple and effective method to keep cigars from drying out.
In the US, TSA doesn't care about cigarettes as they are no hazard to aircraft operation. So there is no need to hide them. You can carry one book of safety matches or 1 lighter on your person, or in your carry on bags. Matches and lighters are prohibited in checked luggage in general.