It’s like a 2 for 1, or better…

Cashing in your credit card points or airline miles is an emotional experience. Great flights seem to require more and more points, and almost always seem to offer less and less. Depending on which airline you book with, you may be entitled to some very generous side trips, requiring no extra mileage whatsoever, helping to extract maximum value from your emotional redemption. Here are the most generous airlines for stopovers when you use your points…

ANA Mileage Club

Transfer Partner Of: American Express (USA), Starwood Preferred Guest/Marriott Rewards.

Best Use Of Points: Around The World In Business Class For 125,000 Points.

Generous Stopover Rules: On all tickets using points that originate outside of Japan, you’re allowed one stopover when you actually fly on ANA. Since all flights go via Tokyo, this is a great way to score a free side trip to Tokyo en route to your final destination. On the amazing around the world tickets using all of Star Alliance, you’re allowed a whopping 8 stopovers, allowing you to see 8 destinations for more than 24 hours. That’s a lot of travel for 125,000 points.

Alaska Mileage Plan

Transfer Partner Of: Starwood Preferred Guest/Marriott Rewards.

Best Use Of Points: Flights Up Front On Partners Like Cathay Pacific, JAL, Qantas.

Generous Stopover Rules: Alaska allows one free stopover per one way ticket! By using clever geographic routings, you can do things like fly from Singapore to Tokyo, stop in Tokyo for multiple days and then fly to Delhi, all for just 25,000 points in business class. Similarly, you can fly Los Angeles to Melbourne, enjoy Melbourne and then head to Perth for no additional mileage. You get one stopover in each direction, which is awesome.

Air Canada Aeroplan

Transfer Partner Of: American Express, Starwood Preferred Guest/Marriott Rewards.

Best Use Of Points: Business class between U.S. and Europe for 110,000 points round trip.

Generous Stopover Rules: Aeroplan allows you to fly great Star Alliance airlines like Air Canada, Swiss, Austrian, Lufthansa and more across the pond. On all round trip awards, even if you go elsewhere, you’re eligible for two free stopovers and an open jaw. This effectively means you could fly from New York to Paris, stop in Paris, fly to London, enjoy London for a few days and then depart from Barcelona, all for just 110,000 points round trip, with the connecting flights in between included.

Japan Airlines Mileage Bank

Transfer Partner Of: Barclays Arrival Premier, Starwood Preferred Guest/Marriott Rewards.

Best Use Of Points: Emirates First Class Asia To Europe With Dubai Stop For 100,000 Points.

Generous Stopover Rules: JAL allows a maximum of three stopovers when you use points for round trip flights on one single partner airline. This means you could add up to three cities onto a trip as simple as Bangkok to Los Angeles. If you use more than TWO OneWorld airlines, the allowed number of stopovers jumps to seven, which is nothing short of wonderful.

United Airlines Mileage Plus

Transfer Partner Of: Chase Ultimate Rewards, Starwood Preferred Guest/Marriott Rewards.

Best Use Of Points: Flights up front on partners in S.E. Asia and Australia.

Generous Stopover Rules: United offers a highly obscure, but very lucrative perk, that essentially works as a buy three get one free. Dubbed the “excursionist perk”, when you book three one way flights, that start and end in the same place (the middle one can be elsewhere), you get a free flight valid in the same class, virtually anywhere in the world. The free flight must stay within one region, like Australia, but it can be used at any time. It’s complicated, so read up here.