Open-Ended Destination Planning

We can’t always have the luxury of leaving the country for extended periods of time, leaving our jobs, homes, family, and friends. Sometimes we just want to take a short trip to get away with a destination unknown. But this kind of trip planning can be challenging with so many options to choose from and a limited budget. I’m all about value, so when I’m searching for these kinds of trips I want the best bang for my buck.

For driving trips (from Chicago), I’ve found forum posts (1, 2, 3) and articles (1, 2) on the topic, but flying is a different story.

Finding that perfect flight to an unknown destination on a strict schedule is challenging. Thankfully, I’ve found a few tools that have been helpful in open-ended destination planning. These are also the tools that I’ve used as I explore routing options for our round the world trip.

Google Flights

Google Flights launched in 2011 after the purchase of ITA Software. If you aren’t aware, ITA is a software package that is being used to manage reservation systems for some of the worlds largest airlines (e.g. United, American, Air France) and travel booking sites (e.g. Orbitz, Kayak, Hotwire).

The search site itself almost seems like a widget because it’s just so simple and basic. But – it’s fast, making it easy to toggle around dates to find the perfect flight. Enter in a departure airport and immediately your destination options will be displayed on a map.


Additionally, you can filter number of stops, airline alliance, price, flight duration, as well as departure and return times.

Kayak Explore

Kayak Explore has a beautiful interface for open-ended destination planning. Plug in your departure airport and departure month or season and you’ll be given a list of destinations from all over the world.


Once you’ve got a destination worth exploring, you can open up a date window allowing you to select specific dates or trip duration and see how the prices change over time around the date selected. Really the coolest thing about it is the 12-month trended bar graph where if you’ve got flexible plans you can scope out the best deal.


Filters for the search include price, flight time, non-stop only, as well as weather and stuff to do (although I haven’t played around with those two options much).


Skyscanner allows you to search “Everywhere” and then grab general prices by country. Once a country is selected, you can pick a specific city as well. There are a lot of clicks involved and sometimes the less than popular routes don’t have prices displayed, but it does a good job of displaying a lot of different options for you.


The biggest downside that I’ve found with Skyscanner is that often times the results will come from a variety of other travel booking sites such as faregeek or ebookers which, mostly because I haven’t used them, I am a little hesitant to book through. Most of my flights are booked directly with an airline.

So that’s it. This is how I spend hours and hours searching for those perfect flights at the right price. Sometimes you’ll get lucky, but most often it takes some patience and flexibility to get the flight you want.

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