Phoenix to Chicago for 56 bucks – How to Piece Together a Cheap Getaway

Let’s be honest, there aren’t a lot of ways to magically save money on airfare. It takes a little bit of work and most importantly, flexibility on your part. If you have rigid travel plans, such as strict dates and destination, it is going to be tough to get the best deal possible. I am going to talk about how to “getaway” for cheap. This is going to involve finding cheap flights to a number of destinations and then deciding to go 🙂

So you love to travel and you want to see our beautiful country? Read on.
One of the most overlooked ways to save money on flights is to book two separate flights, even if it is with the same airline. This can seem very counter intuitive to save money but I am going to show you how it can work.

Many of the cheapest flights are to large airports, this is because airlines usually have competition with other airlines. My favorite way to use this “trick” is by flying on Southwest, but it can work for any airline in theory.

Looking on Southwest’s Getaway Map you can filter to only show cheap destinations and easily toggle dates to see what best flights are available. So where does the trick come into play?

By booking a dirt cheap flight, for example, from Phoenix to Chicago on 8/29 (for $56 one-way), you can use Chicago as your spring board to another airport. $56 one-way is incredibly cheap, so if Chicago isn’t where you want to go (I recommend visiting by the way) then you can see what other cheap flights leave out of Chicago, Chicago would just be your layover.

The first step is to find the cheapest flight you can in the direction you want to travel. If traveling from the west coast, Chicago, Denver, Houston, and Dallas are good cities to start “making your way” to the east coast. Those four cities, being in the Midwest-ish will connect to almost every medium to large city in the country.


How far east can I get for $56? Chicago is a good start
How far east can I get for $56? Chicago is a good start


Now that you landed in Chicago for $56, you can see that there are other cities you can visit for around $50. For example, from Chicago you fly to Baltimore, MD, Atlanta, Ga, Minneapolis, MN, Orlando, FL, and Raleigh, NC.


Five cities you can reach for under $60
Five cities you can get to from Chicago for under $60


Let’s take the Atlanta example, you will be able to get to Atlanta for $56 + $46 = $102. That is a cheap flight to Atlanta. On the cheapest flight booking from Phoenix to Atlanta on 6/30 is $159. That saves you $57. The cheapest flight from Phoenix to Orland on Southwest is $206 and that still has a layover. If you book two separate flights to get to Orlando (with your stop in Chicago for example) you will save $100, and that is just one-way. That will pay for a hotel night or your rental car.



$206 to Orlando and those flights still have layovers
$206 direct to Orlando, but those flights still have layovers


The best part about this little trick is that you can coordinate your flights so that you can spend a day or two in your layover city, like Chicago, if you choose so. This is where you can really start seeing the country for cheap and leverage your layovers.

From the Midway Airport in Chicago (the smaller airport where Southwest flies) you can take public transportation right into the downtown for about $5. It is a 35 minute ride. Once in downtown you can Uber or walk to pretty much anywhere in the urban jungle. Another cool and cheap way to get around is bike rentals. Divvy is a rental company that is vending-machine-like and is located right on the street. They have stations all over town and you can rent a bike for $7 for 24 hours.



Now that is sounding like a fun layover right? And it is cheaper than flying direct 🙂

If you have luggage that you want to leave at the airport while you go into the city for the day many airports offer storage options. You can rental hourly/daily and choose between small and large lockers. It is a great option if you only want to take a backpack or purse with you for the day.


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