How to Book a Flight to Two Different Cities

If you’ve searched for this, you’re probably trying to do one of two things: fly into one city and out of a different one, or visit two (or more) destinations on the same trip without flying home in between. Both are entirely possible, and neither requires anything complicated — but standard flight search engines aren’t always built to make it obvious how.

This guide walks through exactly how to book a flight to two different cities, covering both scenarios, with the practical steps for each.

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First, Which Scenario Are You Actually Booking?

“A flight to two different cities” usually means one of two things, and it’s worth being clear on which one applies to you, since the booking method differs slightly.

Scenario A: Fly into City A, and home from City B You’re flying out to one city, then home from a different city — for example, flying into Paris and home from Rome after travelling overland between them. This is called an open-jaw ticket.

Scenario B: Visit City A, then fly on to City B, before returning home You want to actually fly between the two cities as part of your trip — for example, London to Tokyo, then Tokyo to Seoul, then home from Seoul. This is a multi-city itinerary.

Both are booked in a similar way, but the itinerary you build looks slightly different depending on which one you mean.

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How to Book: Scenario A (Fly Into One City, Home From Another)

Step 1: Use the “Multi-City” Search Option

Almost every major flight search tool — including VoyageFlights, Google Flights, Skyscanner, and individual airline websites — has a search mode labelled “Multi-city,” “Multi-destination,” or similar, separate from the standard “Round trip” and “One way” options. This is the mode you need, even though you’re only adding one extra city.

Step 2: Enter Your Outbound Flight

Set your departure city (e.g. London) and your first destination (e.g. Paris), along with your outbound date.

Step 3: Enter Your Return Flight From the Second City

Add a second flight segment. This time, set the departure city as your second destination (e.g. Rome) and the arrival city as home (e.g. London), with your return date.

Step 4: Leave the Middle Unconnected

Notice that nothing connects Paris and Rome directly in this search — that gap is deliberately left for you to fill with your own travel (train, bus, car, ferry, or even a short separate flight if you prefer).

Step 5: Search and Compare

Run the search. Most tools will price this as a combined “open-jaw” fare. It’s worth comparing this against booking two separate one-way tickets (one into Paris, one home from Rome) to see which comes out cheaper for your specific dates.

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How to Book: Scenario B (Fly Between Both Cities as Part of the Trip)

Step 1: Select “Multi-City” Search

Same starting point as above — you need the multi-city search mode, not round trip.

Step 2: Add Each Leg of Your Journey

Build out your full route as separate flight segments:

• Leg 1: London → Tokyo (outbound date)
• Leg 2: Tokyo → Seoul (date you plan to move on)
• Leg 3: Seoul → London (return date)

Most multi-city search tools let you add as many legs as you need — two, three, or more.

Step 3: Check Each Leg’s Availability and Pricing Together

A good multi-city search tool will price the whole itinerary as one combined fare where possible, which can be cheaper than booking each leg separately, particularly if the airlines are within the same alliance.

Step 4: Verify Your Connection Times Are Realistic

This step is often skipped and causes the most problems later. If any of your legs are close together in time, check that you have enough time to make the connection comfortably — not just the bare minimum a booking system allows. This matters even more if your legs are on different airlines, since a missed connection between unlinked tickets isn’t the airline’s responsibility to fix.

Step 5: Book as a Single Itinerary Where Possible

If your booking tool allows it, book all legs together under one itinerary rather than as separate one-way tickets. This means if one flight is delayed and affects a later connection, the airline is responsible for getting you to your destination — rather than you needing to buy a new ticket yourself.

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Can You Book This Directly on an Airline’s Website?

Yes, in most cases. Most major airlines — British Airways, American Airlines, Emirates, and others — have a “multi-city” or “multi-destination” option directly on their own booking page, usually as a tab alongside “Return” and “One way.” The process works the same way: you add each leg as a separate segment.

The limitation is that you’re restricted to that airline’s own network and its alliance or codeshare partners. A dedicated multi-city search tool like VoyageFlights searches more broadly, which is useful if your two cities aren’t well connected by a single airline.

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Is It More Expensive to Fly to Two Different Cities?

Not necessarily — and sometimes it’s cheaper. A few things to understand:

Open-jaw fares (Scenario A) are often priced similarly to a standard round trip, sometimes within 10-15%, because you’re still only taking two flights total.

Multi-city fares (Scenario B) involve an extra flight leg, so naturally cost more than a simple round trip to one destination — but they’re almost always cheaper than booking two entirely separate round trips to each city, since you avoid an unnecessary return-and-depart cycle through your home city.

The best way to know for certain is to compare: search the combined itinerary, then compare it against booking each leg as a separate one-way ticket, and pick whichever total comes out lower.

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Common Mistakes When Booking a Flight to Two Cities

Searching “round trip” and trying to change the return city manually. Most round trip search interfaces don’t support a different return city — you need the multi-city mode specifically.

Booking each leg through a different website without checking total cost. It’s easy to end up paying more than necessary by not comparing a combined multi-city search against separately booked legs.

Not checking visa requirements for both cities. If your two cities are in different countries, double-check entry requirements for each destination separately, not just your final one.

Underestimating connection time if the two cities are linked by a flight rather than ground travel. A tight connection between your two destinations can undo the savings of a clever routing if you miss it and need to buy a replacement ticket.

Assuming it isn’t possible. This is surprisingly common — many travellers don’t realise multi-city and open-jaw booking exists as an option at all, and end up booking two completely separate round trips (with unnecessary extra flights) instead.

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Frequently Asked Questions

Q: Can I fly into one airport and out of a different one in the same city? Yes — for example, flying into London Heathrow and home from London Gatwick. This works the same way as flying into and out of different cities; just set the two different airports as your outbound arrival and return departure points in a multi-city search.

Q: Do I need to book both flights with the same airline? No, though it can simplify things. Booking with the same airline or airline alliance often (but not always) results in a cheaper combined fare and a single linked itinerary, which is generally lower-risk than mixing unrelated airlines.

Q: What if I want to visit three or four cities instead of two? The same multi-city search process applies — simply add more flight segments to your itinerary. The principle doesn’t change with more destinations, though it’s worth checking each connection individually as the itinerary gets more complex.

Q: Is this the same as a “stopover”? Not quite. A stopover is typically a single, longer break in one connecting city as part of an otherwise standard journey (often offered specifically by an airline’s home hub). A multi-city or open-jaw booking involves genuinely separate destinations you’re choosing to visit, rather than a break in one airline’s connecting hub.

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Final Thoughts

Booking a flight to two different cities is far more straightforward than it might initially seem — the key is knowing to use the “multi-city” search mode rather than trying to force a round-trip search to do something it isn’t built for. From there, it’s simply a matter of entering your cities and dates, comparing the combined fare against separate one-way tickets, and double-checking that your connections (if any) are realistic.

Search your two-city itinerary with VoyageFlights — enter your route, compare fares, and check that everything connects properly before you book.