A Successful One-way Stopover Aeroplan Booking

Aeroplan has a wonderful feature that will let you create your own one-way stopovers for 5000 points per person (review).

Basics of Aeroplan One-way Stopovers

When you book a one-way flight with Aeroplan points, you can add a single stopover (>24 hours) at a different destination for just 5,000 points.
You can add up to 2 stopovers on round-trip tickets. However, two one-way bookings are preferred in case of flight cancellations since there is no reduction in total fees or point requirements.
Aeroplan charges a change/cancellation fee of $100/150 CAD per direction of travel so roundtrip cancellation will cost twice the amount.
Stopovers are not permitted in Canada or the U.S. (can be done in Central or South America).
You cannot backtrack through the same airport, city or country when traveling in one direction.
Your stopover cannot exceed 45 days.
Aeroplan allows one-way awards with up to 6 segments total (including a single >24 hour stopover and remaining <24 hour layovers).
Itineraries booked online with a stopover can have a maximum of 4 segments. If your itinerary contains 4-6 segments, only Aeroplan customer service can complete the booking.
The total distance you fly between your origin and destination in one direction must be less than double the nonstop distance (for example, the non-stop distance from New York to Bangkok is 8677 miles and your total 6 leg flight distance for one-way stopover travel should be less than 17,354 miles).
You cannot combine a stopover with an open-jaw ticket and must continue flying from the same airport at which you arrived. For example, if you booked a flight from JFK to Bangkok via Frankfurt, you must depart from Frankfurt airport to continue your trip to Bangkok. You cannot choose to stop over in Frankfurt and then leave from Munich to Bangkok.

My colleague’s June 2025 trip to Japan

My work colleague has 280K MR points and he asked me to plan a 2-week solo trip to Japan in June 2025. I was glad that he was traveling solo, since it is near impossible to find two business class seats to Japan without a year notice (review).

I looked under the Aeroplan program for available flights and found several days of single business class seat availability from JFK to Tokyo via Delhi, India (see images below). The total travel duration was long (29-34 hours), but he was excited to travel in business class for the first time in his life and wanted to explore the offerings from both Air India and ANA.

Aeroplan one-way stopover in Delhi

I suggested him to stay for 3 days in Delhi and explore nearby attractions (e.g., Taj Mahal) and he was thrilled to do so.

We used the Aeroplan Multi-city/Stopover feature (see image below) to request a stopover in Delhi for 3 days.

The total mileage requirement went up by 5000 miles (see image below).

Our failed attempt to book these flights with ANA mileage club

We tried the ANA Mileage Club Multiple Cities/Mixed Classes search and it found availability for all the individual business class flights (see images below). However, there was the dreaded “error message” at the last step and we did not want to call ANA customer service due to their long call center waiting times.