Imagine flying from New York to Bangkok, spending three days in Tokyo on the way, and paying no extra miles for the stop. That is a stopover award, and it is one of the most underused tricks in award travel. A stopover is a break of more than 24 hours in a connecting city, built into a single award ticket. Several airline programs allow them, some for free, and they can turn one holiday into two. Here is how they work and which programs offer the best ones.

Air Canada Aeroplan is the best stopover program for most travellers: it allows one stopover per one-way award for just 5,000 extra points. That means a trip from the US to Europe via Montreal can include a few days in Montreal for almost nothing. ANA Mileage Club allows stopovers on round-trip awards, and its round-trip requirement actually helps here, because you can build a stopover in each direction. Alaska Airlines allows a free stopover on one-way awards, including on partner airlines, which is unusually generous.

Other programs are less friendly. United no longer offers free stopovers on most awards, and American Airlines dropped them years ago. Turkish Airlines Miles and Smiles allows stopovers in Istanbul and even offers a free hotel night through its stopover program, which is a different and valuable perk. Always check the program's current rules before you plan around a stopover, because they change without much notice.

Start by choosing your final destination and your stopover city, then look for a routing that naturally connects through it. Flying from the US to Southeast Asia via Tokyo, Seoul, or Taipei is a natural stopover. Flying to Europe via Lisbon, Istanbul, or Reykjavik works the same way. Search for the award as a multi-city itinerary on the airline's website, entering your stopover as a separate segment with your chosen dates.

If the website will not price it as one award, call the airline. Phone agents can often build stopover awards that the website cannot price, and the phone booking fee is small compared with the value of a free extra city. Be ready with your exact flights and dates, and have a backup routing in case your first choice has no award space. Flexibility is the key to stopovers: shifting your stop by a day can open up availability.

A stopover adds a city in the middle of your trip. An open-jaw flies into one city and out of another, such as flying into Paris and home from Rome. Both let you see more for the same miles, and they can be combined: fly into Tokyo, stop over in Seoul, continue to Bangkok, and fly home from Singapore. That is a four-city trip on two award tickets, and it is the kind of itinerary that makes award travel feel like a superpower.

The trade-off is complexity. Multi-city awards are harder to find, harder to change, and more vulnerable to schedule changes. Keep your itinerary simple for your first stopover: one stop, a few days, a city you genuinely want to visit. Do not add a stopover in a city you do not care about just because it is free. The point is a better trip, not a more complicated one.

Plan your stopover like a mini-trip, not a layover. Two or three nights is ideal: enough to see the highlights, eat well, and rest, without turning the trip into a marathon. Book a hotel with points if you can, and use the stopover city as a chance to break up a long journey. A three-day break in Tokyo on the way to Bangkok turns a tiring 20-hour journey into two pleasant flights with a holiday in between.

Watch the visa and entry rules for your stopover country, and check whether your checked bags will be transferred or need collecting. Most airlines through-check bags on a single ticket, but confirm at check-in. A stopover is free money in travel form, and once you have done one, you will never book a long-haul award without checking for it first.