I can’t start any discussion about American Airlines without first mentioning that I prefer the American frequent flier program over any of the other major airlines.  Its elite flier program provides complimentary cabin upgrades (space permitting) and its redeemable miles award redemption chart is relatively generous.  In addition, there are a number of ways to earn redeemable miles.

Elite Status

• Costs: you can reach the first tier of elite status, Gold, by flying 25,000 miles in a calendar year.  If you strategically buy cheap plane tickets, you can achieve this with 2.5 round-trip flights to Rio de Janiero ($1,350) or 5 round-trip cross-country flights (JFK-LAX) ($1,250).

• Benefits: Gold status comes with pretty cool benefits including complementary upgrades (space permitting) on flights of 500 miles or less ($300+ per flight), 500 mile upgrades that are used to upgrade flights over 500 miles (cost $40 per 500 mile upgrade), one free checked bag, complimentary preferred seating ($10-50 per flight), and a discount on main cabin extra seating.

Earning Redeemable Miles

• Fly American Airlines or credit flights flown on One World members to American.  Until the second half of 2016, you’ll still receive one redeemable mile per mile flown.  Starting the second half of 2016, you’ll receive miles per dollar spent.  This change will likely benefit folks who buy expensive tickets but hurt those who buy cheap tickets.
• Credit card sign up bonuses.  You can receive anywhere between 35,000 and 75,000 miles depending on the current sign up promotion.  I earned 35,000 miles after meeting the minimum spend requirement for my first travel credit card which was enough miles for an off-season round-trip ticket to Hawaii.  The credit card itself gave me 2 miles per dollar spent on American Airlines and 1 mile per dollar spent on all other purchases.
• American online shopping portal.  The shopping portal allows you to earn additional miles when you shop online.  Simply log into the shopping portal and select the store that you want to shop.  The shopping portal will then take you to that store and will credit your miles a few weeks after the purchase is made.  In addition, the shopping portal will offer bonus mile promotions for Back to School, pre-Black Friday, and other seasonal shopping.
• American dining program.  After linking your credit card to your dining profile, you’ll receive an additional 3 to 5 miles per dollar spent at a participating restaurant.  Restaurant participation is hit or miss, so definitely check out the list of participating restaurants.  I’ve had good luck in DC since one of my favorite coffee shops participates.
• Other promotions.

Redeeming miles for award flights: American is increasing the amount of miles required for most reward flights on March 22, 2016, so I’ll discuss the new award chart.  Despite this increase, there are still a few good deals.  You can redeem 45,000 miles for an off-peak round-trip ticket to Europe and 60,000 miles for a round-trip business class ticket to Machu Picchu (and the rest of northern South America).  It’s also worth noting that miles can be redeemed on One World partners (Cathay Pacific, Qatar, etc.) and other affiliated airlines (Emirates, Fiji, etc.) that may have nicer planes/ service/food than American.