Why pay for two awards when one ticket can send you to four cities?
Most travelers book point-to-point and miss stopovers and open-jaws that stretch a single award into a mini tour.
Think of an award ticket like a Swiss Army knife, one tool with many uses.
This post shows which programs let you add stopovers or fly into one city and out of another, how to find legal routings, and the simple rules to know when the extra planning actually saves miles and money.
How Stopovers and Open-Jaws Expand Award Travel Options
A stopover is when you intentionally pause your award ticket for at least 24 hours in a connecting city. An open-jaw means you fly into one city and leave from another on the same award. Both let you visit multiple places without booking separate trips or torching extra miles. A layover? That’s just a normal connection under 24 hours where you’re stuck in the airport or a nearby hotel, not actually exploring anything.
These tools can turn a boring point-to-point award into a full multi-city trip. Flying Los Angeles to Paris? You might tack on a five-day Reykjavik stopover for zero extra miles on some programs. Or fly into Paris, out of Rome, and cover that Paris-Rome leg yourself while still using one award ticket. Some programs even let you combine a stopover and an open-jaw on the same booking, so you could hit four cities (home, stopover, arrival, departure) on one redemption. Instead of burning 60,000 miles twice for two trips, you visit three or four destinations for 60,000 miles once.
The big wins with stopovers and open-jaws:
- See extra cities without doubling your miles. Add a stopover and visit a second destination on the same award.
- Cut out backtracking and wasted time. Open-jaws mean you skip the return flight to your arrival city and just keep moving forward.
- Lower total taxes and fuel surcharges. One award ticket often means you’re paying international fees once, not twice on two one-ways.
- Simpler itinerary management. Everything lives on one reservation, so rebooking or changes get easier if plans shift.
- Protect your award space. Booking one multi-city award is usually simpler than locking down two one-way saver awards on busy routes.
When you stack a stopover with an open-jaw, you’re basically designing your own tour route. Depart New York, stop in Reykjavik for three days, continue to Paris for a week, train to Madrid, then fly Madrid back to Boston. That hits four cities and crosses the Atlantic twice but costs the same miles as a simple New York-Paris roundtrip on many programs. The trick is knowing which programs allow this stuff, how to search for legal routings, and where hidden fees or restrictions might kill your savings.
Rules and Restrictions Across Major Airline Programs
Not all frequent flyer programs treat stopovers and open-jaws the same. Some let you add multiple stopovers at no extra cost. Others charge a fee per stopover or ban them completely. Region definitions, routing rules, and cabin restrictions swing wildly, so you need to check the fine print before assembling anything complicated.
Aeroplan lets you add one stopover to a one-way award for 5,000 extra points, and you can add up to two stopovers on a roundtrip for 5,000 points each. But Aeroplan won’t let you stopover on awards flying entirely within North America, so no extended Toronto pause on a New York-Vancouver ticket. Alaska Airlines Mileage Plan permits one stopover per one-way and up to two on a roundtrip, but when you use a stopover you can only mix one partner airline plus Alaska on the entire ticket. That means you can’t combine Japan Airlines outbound and Cathay Pacific inbound if you’re taking a stopover. You’d need two one-way awards to use different partners each direction.
Some programs require roundtrips to unlock stopover privileges. ANA Mileage Club only allows stopovers and open-jaws on roundtrip awards (one stopover and one open-jaw per roundtrip). Singapore KrisFlyer’s Saver roundtrip awards allow one stopover and one open-jaw, but Saver one-ways allow zero stopovers. If you want a stopover on a KrisFlyer one-way, you must book the pricier Advantage award, which permits one stopover but costs way more miles. United MileagePlus killed explicit stopover allowances years ago, but the Excursionist Perk can give you a free one-way segment within a multi-city itinerary if you meet region and cabin conditions.
| Program | Stopover Rules | Open-Jaw Allowed | Notes |
|---|---|---|---|
| Air Canada Aeroplan | +5,000 pts per stopover (max 2 on roundtrip) | Yes | No stopovers within North America region |
| Alaska Mileage Plan | 1 stopover per one-way; 2 per roundtrip | Yes | Only 1 partner + Alaska when stopover used |
| ANA Mileage Club | 1 stopover per roundtrip (roundtrip required) | Yes (1 per roundtrip) | High fuel surcharges on many routes |
| Singapore KrisFlyer | 1 stopover on Saver roundtrip; 0 on Saver one-way | Yes (1 per roundtrip) | Advantage awards allow 1 stopover one-way but cost more miles |
| Cathay Pacific Asia Miles | Up to 5 stopovers (max 50,000 flown miles total) | Yes (up to 2) | Mixed cabin priced at highest cabin for entire trip |
| United MileagePlus | No formal stopover; use Excursionist Perk | Yes | Excursionist must meet region and cabin rules to be free |
Booking channels matter too. Aeroplan’s website lets you add stopovers directly in the multi-city search tool, but Flying Blue makes you call 1-800-375-8723 to book stopovers on Air France or KLM-operated awards. Some programs show stopover options during online search. Icelandair, for example, prompts you to add a free Iceland stopover up to seven nights when searching U.S. to Europe routes. But most complex multi-city awards require calling the award desk with your desired routing written out segment by segment.
Step-by-Step Guide to Booking Stopovers and Open-Jaws
Booking a multi-city award with stopovers or open-jaws takes more work than a simple roundtrip, but the process is manageable if you break it into clear steps.
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Map your desired route and estimate flown distance. Write down each city you want to visit in order: departure city, stopover city (if any), arrival city, departure city for the return leg (if different), final home city. Use a tool like gcmap.com to calculate total flown mileage if the program uses distance-based pricing (Alaska, ANA, JAL). Make sure your total distance fits within the program’s award chart bands.
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Check the specific program’s stopover and open-jaw allowances. Look up whether the program allows stopovers on one-way awards, how many stopovers you get, and whether there’s an extra mileage fee. Confirm regional restrictions. Aeroplan won’t let you stopover within North America, and some programs require the stopover to happen at a partner hub.
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Search for award availability segment by segment. Use the airline’s own award search tool or partner search engines to confirm that saver-level space exists for each flight you want. If you’re flying United and ANA on an ANA award, search United space on United.com and ANA space on the ANA website. Write down flight numbers, dates, and fare classes.
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Use the program’s multi-city or advanced search tool. On Aeroplan, Alaska, or United, select the multi-city search option and enter each segment. On programs without solid online tools (Flying Blue, sometimes KrisFlyer), prepare to call the award desk with your segment list.
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Verify region definitions and routing rules. Programs define regions differently. United’s Europe region includes North Africa and the Middle East, while Aeroplan splits them up. Confirm that your stopover city and open-jaw cities fall within the rules. The United Excursionist Perk requires that the free segment start and end in the same region, and that region must differ from your origin and final destination region.
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Calculate total taxes, fees, and fuel surcharges before booking. Enter your full itinerary into the award booking tool or ask the phone agent for the final price breakdown. Watch for carrier-imposed surcharges. Awards routed through London Heathrow or starting in Europe can add $200 to $400 or more per person. If surcharges are high, consider alternate routings on carriers that don’t impose them (United, Air Canada, LOT, Turkish).
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Book the award and request e-ticket confirmation. Complete the booking online or confirm all segments with the phone agent. Ask the agent to read back each flight number, date, and booking class to catch errors before ticketing. Request that the e-ticket be sent to your email, then verify every segment in your reservation.
If the award search engine throws an error or won’t price your routing, the system might not recognize a legal stopover or open-jaw. Call the program’s award desk. Explain the routing you want, reference the program’s published stopover rules, and ask the agent to manually price the itinerary. Some agents know complex awards better than others, so if the first agent says it’s impossible, politely hang up and call back to try another agent. The booking might take 20 to 40 minutes on the phone, but unlocking a multi-city award for one redemption is usually worth the hold time.
Real Examples of High-Value Stopover and Open-Jaw Itineraries
Knowing the theory is useful, but seeing real routings with actual mileage costs makes the whole thing concrete.
Europe routings: Use Aeroplan to fly Los Angeles to London on United, add a five-day stopover in Reykjavik on Icelandair for 5,000 extra Aeroplan points, then continue to Athens on Aegean Airlines. The entire one-way costs around 90,000 Aeroplan points in business class plus the 5,000-point stopover fee, visiting three cities for the price of a standard transatlantic business award. Or book a roundtrip from New York to Paris with an open-jaw return from Madrid to New York. You cover the Paris to Madrid train or budget flight on your own, but the award mileage stays the same as a simple New York-Paris roundtrip, often 60,000 miles in economy or 115,000 in business.
Asia routings: Alaska Mileage Plan lets you fly San Francisco to Taipei on Starlux, add a stopover in Tokyo on Japan Airlines, then continue to Bangkok on the same award. That routing uses two partners, so you’d need to structure it as San Francisco to Tokyo (stopover) to Bangkok on Japan Airlines for 50,000 Alaska miles in economy or 70,000 in business, visiting two major Asian cities. On Singapore KrisFlyer, book a Saver roundtrip from Los Angeles to Singapore with a stopover in Tokyo (on Singapore’s fifth-freedom LAX-NRT flight) for around 100,000 KrisFlyer miles in business class roundtrip, letting you explore both Tokyo and Singapore.
South America and beyond: Use Aeroplan to fly Miami to Zurich, stopover for a week, then continue to Naples on the same award for 75,000 Aeroplan points in business class. Or build a more complex itinerary on Cathay Pacific Asia Miles: depart New York to Paris on American, stopover in Paris for four days, continue Paris to Dubai on British Airways, stopover in Dubai for three days, then fly Dubai to Bangkok on Qatar and return Bangkok to New York on Cathay Pacific. That routing uses five segments, four airlines, and two stopovers within the 50,000 flown-mile maximum, costing around 140,000 Asia Miles in economy or 265,000 in business. Visiting four major cities on one award.
| Itinerary | Program | Mileage Cost | Why It Works |
|---|---|---|---|
| LAX → LHR (stopover) → ATH | Aeroplan | 90,000 + 5,000 pts (business) | Adds London city visit for only 5,000 extra points on transpacific business award |
| SFO → NRT (stopover) → SIN | Singapore KrisFlyer | ~100,000 miles RT (business) | Free stopover on fifth-freedom route lets you see Tokyo + Singapore |
| NYC → CDG; return MAD → NYC | Most programs | Standard roundtrip rate | Open-jaw saves backtracking; you cover Paris-Madrid separately via train/budget flight |
| MIA → ZRH (stopover) → NAP | Aeroplan | 75,000 + 5,000 pts (business) | Visit Swiss Alps and southern Italy on single transatlantic business award |
| JFK → CDG → DXB → BKK → JFK (2 stopovers) | Cathay Asia Miles | ~265,000 miles (business) | Four cities, multiple carriers, within 50,000 flown-mile cap; extreme value if you find space |
These examples show how stopovers and open-jaws let you design itineraries that would cost two or three separate awards if booked individually. The key is finding award space on each segment and making sure your routing obeys the program’s published rules.
Common Mistakes and How to Avoid Them
Even experienced travelers screw up when booking complex awards. The most frequent mistake is assuming all programs allow the same stopover and open-jaw rules. Travelers design a dream itinerary, then discover mid-booking that the program prohibits stopovers in certain regions or only allows them on roundtrips. Always verify the specific program’s rules before searching for flights.
Another common pitfall is exceeding the program’s maximum permitted mileage or segment count. Cathay Asia Miles caps itineraries at 50,000 flown miles. If your routing pushes past that, the system won’t price it. Japan Airlines allows up to six segments excluding the open-jaw, but adding a seventh segment breaks the award. You must calculate total flown distance and count segments before finalizing your routing.
Frequent booking errors:
- Routing through high-surcharge airports without checking fees. Awards via London Heathrow, Brussels, or starting in Europe can add $200 to $400+ in fuel surcharges that wipe out your point value.
- Mixing too many partners on programs that limit partner counts. Alaska only allows one partner airline when you use a stopover, so booking United outbound and Cathay inbound with a stopover won’t work.
- Not confirming partner blackout dates. Just because you see award space on the partner’s website doesn’t mean the program you’re booking through can access it. Some partners block certain routes or dates from redemption via other programs.
- Assuming mixed-cabin awards price per segment. On Cathay Asia Miles and several other programs, mixed-cabin itineraries price at the highest cabin for the entire trip, so one first-class segment makes the whole award cost first-class miles.
- Ignoring regional definitions. United’s Excursionist Perk requires precise region alignment. If your “free” segment crosses into a different region, it won’t price at zero miles.
- Forgetting to verify stopover duration limits. Singapore KrisFlyer caps stopovers at 30 days. Emirates caps Saver stopovers at shorter windows depending on fare rules.
Before you book, double-check the program’s routing rules one more time. Pull up the official award chart, confirm region boundaries, and verify stopover allowances for your ticket type (one-way vs. roundtrip, Saver vs. Flex). If you’re unsure whether a routing is legal, call the award desk and ask the agent to confirm before you transfer points. Once points are transferred, most programs don’t let you reverse the transfer if the award you wanted turns out to be unbookable. Spending ten minutes on a phone call can save you from burning miles on a terrible routing or, worse, finding out the itinerary is impossible after you’ve already moved 100,000 points into the program.
Final Words
Use stopovers and open-jaws to stretch one award into a real multi-city trip without paying full extra miles. We defined both moves, showed which programs are generous, walked through step-by-step booking, and gave real high-value examples.
Watch the program rules and common mistakes—those are where cheap plans turn expensive. Test routes on a multi-city search, confirm partner availability, and double-check fees before you hit buy.
Practice pays off. Start small and you’ll soon be using stopovers and open-jaws on award bookings to see more for less.
FAQ
Q: What is the difference between open jaw and stopover?
A: The difference between an open-jaw and a stopover is that an open-jaw has you fly into one city and out of another, while a stopover is a planned break (usually over 24 hours) in a connection city.
Q: What is the 3-3-3 rule for flights?
A: The 3-3-3 rule for flights is a loose planning guideline: arrive about 3 hours before international departures, allow 3 hours for risky connections, and expect roughly 3 days to adjust to big time-zone changes.
Q: What is an example of an open jaw itinerary?
A: An example of an open-jaw itinerary is flying into Paris and returning from Rome, handling the land leg between cities separately so your arrival and departure airports are different.
Q: What is stopover in award travel?
A: A stopover in award travel is a planned stay in a connecting city longer than 24 hours that some programs allow without extra miles, though specific rules, regions, and fees vary by airline.