Business Class fares are a mixed bag these days. We’re finding great fares one day, and grate fares the next. Well, they grate on my nerves when I see them. So it got us thinking — what if we got a bit lateral about the departure and arrival cities? Instead of just accepting the high fare, why not cast your net a little wider in terms of the cities you leave from and arrive to? Sometimes an alternative city is surprisingly close and offers a much better fare — which would way more than cover the cost of the short trip to get there.
This “sidestep hustle” is a handy hack when fares are high out of a major U.S. city like Chicago or New York. Let’s look at some examples.
Sidestep Hustle #1 Alternate U.S. Departure City
A typical Business Class fare on American Airlines from Chicago to Frankfurt is $5,426. Instead, you could sidestep to Milwaukee and fly from there to Frankfurt in Business Class on American for only $3,361. Milwaukee is just 67 miles from Chicago, a short trip for a $2,065, or 38%, savings. That could be a short “positioning flight” or even a car trip. Either way, you’re well ahead. Screenshots follow.
Chicago to Frankfurt for $5,426

Milwaukee to Frankfurt for $3,361 on American

Alternate U.S. Departure Cities
It’s not just the Chicago/Milwaukee sidestep that works. Here’s a range of alternative departure options for nearby cities across the three alliances on major carriers.
ONEWORLD alliance
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skyteam alliance
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star alliance
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And, it’s not only the U.S. departure cities that offer lots of alternatives. Arrival cities in Europe do so too, as this example shows.
Sidestep Hustle #2 Alternate International Destination
A typical fare on Delta from New York to Vienna costs $5,090. So why not look at a nearby alternative — Budapest, for example? Budapest is only 133 miles from Vienna, and yet the New York-Budapest fare is just $2,609, a savings of $2,481, or 49%. That’s an incredible price difference considering the 133-mile gap. You could take a high-speed train between the cities. Those take around 2 hours and 15 minutes and offer gorgeous scenery from rolling hills to quaint villages and dense forests. Or stay in Budapest for a few days; it’s a beautiful city.
Delta New York to Vienna for $5,090

Delta New York to Budapest for $2,609

Alternate International Destination
oneworld alliance
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skyteam alliance
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star alliance
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Sidestep Hustle Is Just One of Many Upgrade Tools in Your Kit
It’s easy to be one-dimensional when it comes to travel. We can literally get set in our ways. For example, many Chicagoans would never think to go to Milwaukee for a better deal, and yet there it is, just 133 miles away. The same approach applies to the destination city. Here are some other smart travel plays to make you a winner.
We mentioned position flights above, here’s more about them. Positioning Flights: FCF’s Mindset on Getting Where the Getting is Good
Maybe you’re thinking about travel the wrong way around. Here’s where you’ll find out. Are You An Opportunity Traveler?
The IAP is a no-brainer for easy savings. Knock off hundreds of dollars (and sometimes even thousands) on lots of premium fares on 26 airlines, thanks to Amex’s International Airline Program (IAP).
FCF’s Rare Fares page has all the needles without the annoying haystack. Here’s… How to Leverage FCF’s Special Fare Finder
Airline hold policies are a handy tool you can use for finding a better fare after you’ve already bought your ticket. Hold This, Dear: A Way to Have Your Deal and Fly It Too
Come to think of it, there are still lots of ways to upgrade after you have a ticket in hand. Buy the Dip, Upgrade Your Trip
As we said in the intro, prices are up and down right now, so here’s a strategy to even out the roller coaster ride. Seeing Rollercoaster Fares? Have FCF’s 2-Step Plan in Your Pocket
And finally, we always talk about being as flexible with dates, airlines, and routes as you possibly can — until you can’t. So here’s a plan. If You’re NOT Flexible: 11 Ways to Save on Premium Flights.