Stopovers and Open Jaws: How to Turn One Trip Into Two

By The Award Hacker Team

Published September 24, 2026

Here's the closest thing to a free lunch in award travel: some frequent-flyer programs let you visit two cities for the miles price of one. Fly from the US to Lisbon, spend four days there, then continue to Barcelona — all on a single award ticket that costs barely more than the direct flight. The mechanisms are called stopovers and open jaws, and they're the most underused beginner-friendly trick in the hobby. Here's exactly how they work and which programs still offer them.

What a stopover is, in plain English

A stopover is a planned stay of more than 24 hours at a connecting city on your award ticket. Picture this itinerary:

New York → Lisbon (stay 4 days) → Barcelona → New York

On a normal booking, that's two trips. With a stopover-friendly program, it's one award: US to Europe with a stopover in Lisbon. The airline was going to route you through a hub anyway; instead of a 2-hour layover, you stay four days and explore a second city.

The key detail: the stopover must be on a valid routing for the award. You can't stop in Tokyo on a New York–London ticket — that's not on the way. But a stop in a partner hub city en route (Istanbul on Turkish Airlines, Toronto on Air Canada, Taipei on EVA) is exactly how these are designed to work.

What an open jaw is, and why it's easier than it sounds

An open jaw means flying into one city and home from a different one:

New York → Lisbon   ...then, days later...   Barcelona → New York

You get yourself from Lisbon to Barcelona however you like — a $60 budget-airline hop, a train, a rental car. Most programs price open jaws as half of each round-trip, which typically totals the same as a normal round-trip award. It sounds exotic, but booking it is usually just the multi-city search box on the airline's website. Open jaws are allowed by nearly every program; they're the easy win to pair with a stopover.

Combine both and you get the classic power itinerary: New York to Lisbon (stopover 4 days), on to Rome (your "destination"), then fly home from Athens on an open jaw. Three countries, one award ticket.

Which programs still allow free stopovers (and their specific rules)

Stopover policies change, so treat this as a starting map and verify current rules before planning. At time of writing, the friendliest programs include:

• Alaska Airlines Mileage Plan — famously allows one stopover on one-way international awards, even on partner itineraries. The stopover can be in a different city than the "destination" in creative routings.
• Air Canada Aeroplan — allows one stopover per one-way for a modest additional points fee (historically 5,000 extra points), with generous routing rules.
• United MileagePlus — no longer offers free stopovers on most awards (its old generous policy ended years ago), but its "Excursionist Perk" successor rules are worth checking if they return in any form.
• Avianca LifeMiles — generally does not allow stopovers; price each leg separately if you're using LifeMiles.

The practical takeaway for a beginner: Alaska and Aeroplan are the two programs to learn first if stopovers excite you. Both accept transfers from major bank currencies, so your transferable points give you access.

Worked example: pricing a two-city Europe trip vs. two separate tickets

Let's put numbers on it. Say you want New York → Lisbon (4 days) → Barcelona, then home from Barcelona.

Without a stopover: you'd book New York–Lisbon round-trip (say 60,000 miles) plus a separate Lisbon–Barcelona flight. The intra-Europe leg might be 15,000 miles or ~$80 cash. Total: roughly 75,000 miles plus extra fees, across two tickets.

With a stopover via Aeroplan: New York to Barcelona with a stopover in Lisbon prices as one award — roughly 60,000 miles in economy plus 5,000 for the stopover, so ~65,000 miles total, one ticket, one set of fees. You save ~10,000 miles and skip the second booking entirely. Then fly home from a different city on the return for the open-jaw version at no extra miles.

The savings scale in business class, where stopovers can save 20,000–40,000 miles on a single ticket. That's the difference between affording business class and not.

How to actually book one: which sites handle multi-city award searches

1. Confirm the program allows it. Check the program's current stopover rules and routing limits (maximum miles flown, permitted regions) before you search.
2. Use the multi-city award search. On Alaska's site or Aeroplan's site, select "multi-city" and enter each leg with your stopover dates: New York to Lisbon (Day 1), Lisbon to Barcelona (Day 5), Barcelona to New York (Day 10). The site should price it as one award if the routing is valid.
3. Verify each leg has saver availability. A stopover itinerary is only as strong as its weakest segment. If one leg lacks saver space, adjust dates before you commit.
4. Book by phone if the site chokes. Complex routings sometimes fail online. The program's award desk can usually price and ticket what the website can't — a phone booking fee may apply, but it's often waived when the itinerary can't be booked online.
5. Transfer points last. As always: find the itinerary, confirm the price and fees, then transfer and ticket immediately.

Common mistakes: married segments, backtracking rules, exceeding mileage caps

• Married segments: airlines control award availability by origin-destination pair, not by individual flight. New York–Lisbon might show space while New York–Lisbon–Barcelona doesn't, even though the first flight is identical. If a multi-city search fails, test each leg separately to find the blocker.
• Backtracking: most programs won't let your routing double back — flying New York to Lisbon, then back west to the Azores, then east again to Barcelona will usually be rejected. Keep the direction of travel consistent.
• Mileage caps: partner awards often have a maximum permitted mileage (typically 25% over the direct distance). A wildly indirect routing — New York to Barcelona via Tokyo — will price as multiple awards or be rejected outright.
• Fees on the extra leg: stopovers can add airport taxes for the extra departure city. Always check the fee total before transferring; a stopover that adds $200 in surcharges may not be worth it.

Stopovers reward the planner. Spend an evening learning one program's rules — Alaska's or Aeroplan's — and your next Europe trip can quietly become a two-city trip for nearly the same miles.