How to Find a Common Destination From Multiple Cities

You’re trying to plan a trip with three friends. One’s in Chicago, one’s in Miami, the third just moved to Denver. You’re in New York. Everyone has limited PTO and a budget that doesn’t include “fly to whoever’s city and then fly somewhere else together.”

So you need a place everyone can reach directly. No connections. No 14-hour layover in Atlanta.

Sounds simple. It isn’t.

The spreadsheet spiral

Most people start by googling flights from their own city. Then they text the group: “What about Cancún?” Someone checks — no direct flight from Denver. Okay, what about San Juan? Works for three of you, not the fourth.

This goes on for a while. Someone builds a spreadsheet. Someone else sends a link to Google Flights that only shows their own departure city. The group chat gets long. Nobody’s booked anything.

The core issue: you’re searching one city at a time, then cross-referencing manually. With two cities, it’s manageable. With three or four, the number of combinations explodes.

What you actually need

A list of destinations that have direct flights from all your cities. Not most of them. All of them. That’s the filter that matters.

Midway does exactly this — you enter your cities, and it returns only the destinations reachable by direct flight from every single one. Takes about ten seconds.

But whether you use a tool or do it manually, here’s the logic:

1. Get the list of nonstop destinations from each airport
2. Find the intersection
3. Filter by what actually makes sense (season, budget, trip length)

Step 1 is available on any airline’s route map. Step 2 is where it gets tedious. Step 3 is where the real decisions happen.

Fewer options is a good thing

Four cities might overlap on only 8–12 destinations. That feels limiting. It’s actually a relief.

When you’re planning with a group, unlimited options are the enemy. Everyone has opinions. Everyone has a place they’ve “always wanted to go.” Narrow the list to what’s actually possible and suddenly the conversation gets productive.

“We can do Cancún, Fort Lauderdale, Las Vegas, or Los Angeles” is a conversation that ends in five minutes. “Where should we go?” is a conversation that never ends.

Think about what happens after the flight

Direct flights get everyone there. But the destination still needs to work for the group. A few things worth checking:

Cost on the ground. Las Vegas and Cancún are cheap to fly to, but Vegas adds up fast if you’re not careful. Cancún all-inclusives can actually be the budget-friendly move for groups.

Accommodation for groups. Hotels get expensive when you’re booking 3–4 rooms. Destinations where Airbnbs or vacation rentals are plentiful — beach towns, ski towns — tend to work better for bigger groups.

Stuff to do that doesn’t require consensus. The best group destinations have enough variety that not everyone needs to do the same thing every day. Beach plus city works. A place with only one activity doesn’t.

When schedules don’t line up

Someone can only do a long weekend. Someone else has a full week. This changes the calculus.

Short trips favor closer destinations. If you’re all domestic (US), a 3-hour flight radius keeps the travel-to-fun ratio reasonable. International trips need at least 4–5 days to justify the airfare and jet lag.

Also worth knowing: direct flight availability varies by day of the week. A route might exist on Saturdays but not Tuesdays. If your dates are tight, check the specific days — not just whether the route exists in general.

The budget conversation

Have it early. Not “roughly how much do you want to spend” — that’s too vague. More like: “Are we talking $500 all-in or $1,500 all-in?”

The destination list from your overlapping direct flights will naturally sort into tiers. Domestic beach towns on one end, European cities on the other. Knowing the budget before you start comparing saves everyone from the awkward moment when someone suggests Lisbon and someone else was thinking Myrtle Beach.

Just pick one

The biggest risk in group trip planning isn’t picking the wrong destination. It’s never picking one at all. Analysis paralysis kills more trips than bad weather.

Get your shortlist. Vote. Book. The trip you actually take beats the perfect trip you’re still planning in six months.