Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Think Outside the Box When Searching for Deals

When it comes to finding cheap flights, most people have a tendency to think inside the box. We search on the major flight search engines like Expedia, check our favorite airline websites, and call it a day. But to find the truly insane, once-in-a-lifetime flight deals, you need to start thinking outside the box.

One out-of-the-box strategy is looking at airports in neighboring cities. For example, if you live in Dallas but are willing to make the 3 hour drive to Oklahoma City, you may find flights that are significantly cheaper out of OKC rather than DFW. This is because smaller regional airports tend to have less demand, so airlines offer great deals to fill seats. The savings can be hundreds of dollars on international flights.
Alternative airports can also open up new route options that may be cheaper. Flying internationally out of O'Hare versus Midway in Chicago can save big bucks depending on your destination. Shop flights from all airports within driving distance to unlock deals you won't find otherwise.
Speaking of new routes, keep an eye out when airlines announce new nonstop flights to uncommon destinations. These routes are often priced low initially as airlines try to build demand. For example, when French Bee launched their nonstop Newark to Paris flight, they had $139 one-way fares in economy to get people excited about the new option.
Finally, don't limit yourself to nonstop flights. While direct is ideal, one-stop flights can also have crazy low fares, especially when the connection is in a smaller hub city. These airlines need to fill seats on the first leg of international journeys, and will offer deep discounts to do so. The inconvenience of a short layover is often worth hundreds in savings.

What else is in this post?

1. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Think Outside the Box When Searching for Deals
2. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Consider Alternative Airlines and Airports
3. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Be Flexible with Travel Dates and Times
4. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Use Airline Sale Calendars to Your Advantage
5. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Follow Flight Deal Blogs and Alerts
6. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Leverage Airline and Hotel Point Transfers
7. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Look for Package Deals and Error Fares
8. Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Maximize Rewards Programs for Free Flights

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Consider Alternative Airlines and Airports

When searching for deals, most travelers default to the major legacy carriers like American, United, and Delta. But you may be missing out on major savings opportunities by not considering alternative airlines. Regional carriers, low-cost airlines, and even international carriers can unlock cheaper fares, even when flying domestically.
For example, British Airways and Aer Lingus often have very competitive fares from the East Coast to Ireland and the UK. So don’t rule them out for your next trip across the pond. Norwegian Air is another one to watch that offers cheap fares from the U.S. to Europe, especially for last-minute deals.

Domestically, ultra-low-cost carriers like Frontier, Spirit, and Allegiant open up opportunities for dirt cheap base fares. As long as you’re flexible with your schedule and fine with paying extra for carry-on bags, you can score deals for a fraction of the price of legacy airlines.
Smaller regional airlines can also offer competitive fares on underserved routes, like JSX's flights between Phoenix and Burbank. These niche carriers cater to local demand rather than relying on connections.
When it comes to airports, look beyond just the main international gateways. Alternative airports in neighboring cities often provide cheaper access to destinations, especially when they serve as hubs for low-cost carriers.
For example, Southwest flies out of Chicago Midway, not O’Hare. So if you're willing to start your trip from Midway, you can score much cheaper Southwest flights around the country. Providence, RI can also be a cheap alternative for accessing Boston on ultra-low-cost carrier flights.
Even small regional airports can unlock deals that the major airports don’t offer. Long Beach Airport has cheap flights to several West Coast cities since it’s a focus city for JetBlue. Palm Springs and Ontario airports provide low-cost access to SoCal destinations as well.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Be Flexible with Travel Dates and Times

One of the biggest factors in finding crazy cheap flights is flexibility. Being willing and able to travel on less convenient dates and times opens up a world of deals that just aren’t possible on rigid itineraries.

A prime example is opting for red-eye flights. These overnight hops are usually the cheapest departure times, often hundreds less than a daytime flight. Why? Most business travelers need to work upon landing. And families with kids prefer to avoid redeyes. That leaves mostly budget leisure travelers willing to sacrifice sleep for savings.

Another key - don’t fly on weekends if you can avoid it. Fridays and Sundays are by far the most expensive travel days. And Saturdays aren’t much better. Opting for a Tuesday through Thursday trip can bring base fares down significantly. Again, it comes down to demand - most vacationers want to maximize time off work and leave on Fridays. Avoid the crowds and save big.
Being flexible on seasonality also opens up great flight deals. Peak summer is expensive for a reason - everyone wants to travel when kids are out of school. But traveling in shoulder seasons of spring and fall brings warmer weather with way cheaper airfare. Goes for saving money by heading somewhere cooler in peak summer rather than joining the crowds headed to the beaches.

The most flexible travelers go even further, planning trips during rainy or cold winter seasons. Places like Europe that depend on tourism income offer rock bottom rates to attract off-season visitors. Sure you may get some bad weather, but the sights will be far less crowded and you’ll save enough for an epic summer trip next year. Well worth it.
Even choosing less popular destinations during their off-peak seasons pays dividends. Paradise islands like the Maldives offer rainy season rates at half the cost of high season visits. And ski towns offer summertime fun at a fraction of the cost of winter lodging and airfare. Follow the good weather and avoid crowds for the best deals.
At the micro level, flexibility even comes down to departure time of day. Morning and evening flights tend to be most expensive as business travelers depart and arrive home. But mid-day and overnight red-eyes offer the cheapest rates to bargain shoppers.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Use Airline Sale Calendars to Your Advantage

One of the best ways to score ridiculously cheap flights is to take advantage of airline sale calendars. Savvy travelers plan their trips around these sales cycles to snag the lowest fares.
Most major airlines run sales at predictable intervals year-round. For example, Delta often hosts three-day sales with discounts around major holidays like Memorial Day, July 4th, Labor Day, etc. American and United follow similar seasonal sale patterns.

These are typically 72-hour sales with deep discounts when you book by the deadline. We’re talking roundtrip fares in the $99-$300 range domestically and under $500 to Europe or South America. Deals that seem too good to be true.
The key is planning ahead and being ready to book when sales launch. Sign up for airline email alerts about upcoming promotions so you’re notified right when the deals go live. Set calendar reminders for yourself as well so you don’t forget.

Scott's Cheap Flights also compiles airline sales calendars across all major carriers. Following their calendar provides an easy way to see the best upcoming deals across airlines all in one place.
When sales launch, you typically have just 72 hours to purchase tickets. So know your destination and travel dates ahead of time. Be ready to pull the trigger on bookings fast before the cheap fares sell out.

Anecdotal evidence on travel blogs shows these airline sales deliver on ridiculously low fares. One writer scored San Francisco to Cancun for $147 roundtrip including taxes by pouncing during a Frontier sale. Others have snagged cross-country hops for under $200 roundtrip thanks to perfectly timed American Airlines promos.
Occasional sales even deliver business class deals approaching economy prices. One lucky traveler booked Newark to Honolulu in United’s Polaris business for just $60 more than economy thanks to a well-timed promotion.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Follow Flight Deal Blogs and Alerts

One of the best ways to find ridiculously cheap mistake fares and flight deals is to follow blogs and alerts focused exclusively on uncovering low airfares. The flight deal gurus behind these sites and newsletters have turned cheap flight finding into a science. They know where to look, when to pounce, and how to take advantage of short-lived deals and glitches before airlines catch on.
While fare mistakes regularly pop up, they never last long once discovered. Usually just a few hours or a day at most before the rates are gone or hiked back up. This is why real-time monitoring and lightning fast alerts are so critical to scoring these unicorns of airfare deals.

The best flight deal blogs have teams constantly scouring flight data, fare calendars, and airline sites across the web. At the first sign of an abnormally cheap fare, they blast out an alert via email and social media to their followers. Website posts also provide context around the cheap find, like departure cities, travel periods, and steps to book fast before it disappears.
For example, Thrifty Traveler will send out flash sale alerts for deals like Chicago to Barcelona for $250 roundtrip that they spot on Iberia's Spanish language site. Or Airfare Spot will discover a Hawaii mistake fare under $200 roundtrip from the West Coast buried deep on United's website. Thanks to their tireless work, you can swoop in at lightning speed to score deals that seem too good to be true.
Subscribing to these flight deal alerts is free and well worth it. The savings regularly run into the hundreds or thousands of dollars compared to normal airfares. And you don't have to waste hours searching yourself - the deals come directly to your inbox when found. Just be ready to book quickly, usually within a few hours, before the rates jump back up or other travelers buy out all the deeply discounted seats.
Travel bloggers like Gilbert Ott and Zach Griff regularly share their own favorite flight deal blogs and how much they've saved from subscriber alerts. Ott scored a $150 roundtrip fare from New York to Madrid, while Griff flew from Los Angeles to Maui for just $98 roundtrip. Not bad for an hour or two spent hastily booking after receiving a golden flight deal alert.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Leverage Airline and Hotel Point Transfers

One underutilized strategy for scoring nearly free flights is maximizing frequent flyer programs and leveraging point transfers between airline and hotel partners. Most major hotel chains from Marriott to Hilton team up with airlines to allow customers to transfer points between programs. Savvy travelers take advantage of these partnerships to shift points and miles where they're most valuable.
For example, Citi ThankYou cardholders can transfer points to airline partners including JetBlue and Avianca LifeMiles. Just 60,000 ThankYou points can book a roundtrip flight to Europe in business class that would normally cost over $3,000 - getting 5 cents per point in value.

On the hotel side, World of Hyatt points can be transferred 1:1 to Hawaiian, Singapore, and other airline programs. 60,000 Hyatt points could score a lie-flat business class seat on Singapore Airlines' new A350 nonstop between NYC and Singapore. A flight that retails for $5,000 or more.
Not only do transfer partners unlock high value redemptions, they also provide flexibility if you're short on miles with one airline. Transferring points in from hotel programs allows you to book Award flights you otherwise couldn't access.

Partnerships also regularly offer transfer bonuses of 5,000 points or 10% extra for free when you move points between programs. Time these bonuses right and you maximize your redemption value even further.

Just be aware of transfer times - hotel to airline transfers can take up to 48 hours in some cases. Avoid last-minute transfers when possible so your points are confirmed in the airline account ahead of booking flights.

While transferring points does provide exceptional value, it also takes more time and planning compared to straightforward ticket purchases. You have to actively monitor both programs for the best redemption opportunities. And ensure you have adequate points balances across accounts to transfer.
But travelers like One Mile at a Time's Ben Schlappig leverage airline and hotel transfers to fly first and business class internationally almost exclusively. And enjoy hundreds of dollars in value from points that originally cost them just a penny each by opening travel reward credit cards. Yes, it involves some effort, but flying Singapore Suites or Emirates First Class to Europe for pennies on the dollar is worth learning transfer partners and options.
The key is understanding transfer ratios between hotel and airline programs, avoiding close-in booking fees, and spotting opportune promotions. Services like Point.me make this easy by showing you all current transfer options between your points and miles accounts.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Look for Package Deals and Error Fares

One of the sneakiest ways to uncover crazy cheap flights is looking for airfare packaging mistakes and error fares. Savvy travelers keep an eye out for deals where flight pricing algorithms glitch and offer prices well below normal market rates. These unicorn fares are rare but with a bit of luck and persistence, you can swoop in for once-in-a-lifetime savings.

Package deals occasionally suffer glitches where one component is drastically underpriced. For example, a hotel + flight combo where the flight portion is 90% off normal rates due to a pricing error. Eager travelers have scored deals like NYC to Paris in fall for $250 roundtrip as part of a package including four nights at a luxury hotel. That’s over $1,000 in flight value priced at a fraction of retail.

These package errors sometimes last days or weeks before systems catch the mistake pricing. I always make it a habit to check packages to destinations I’m interested in visiting, sorting price low to high. You never know when a unicorn deal may pop up.

A common example is business class fares showing up for economy pricing on niche routes. One lucky searcher landed LAX to Bordeaux, France in lie-flat business for just $425 roundtrip thanks to an Air France mistake fare. A steal compared to the usual $5,000+ price tag.
That’s why services like Secret Flying provide alerts when verified error fares appear. Their team vets deals to confirm legitimate mistakes before blasting out alerts. Recent finds include Hawaii from California for $78 roundtrip and Europe deals under $250 from all over the US.

The key is verifying bookability instantly and completing ticketing fast. Error fares disappear quickly, often within 24 hours max. Savvy travelers pre-save payment details and passenger info in airline apps to checkout in minutes.

Cheap Flights to Anywhere But Boring: How to Find Crazy Low Fares to Exciting Destinations - Maximize Rewards Programs for Free Flights

Maximizing frequent flyer and hotel rewards programs can unlock nearly free flights and dream vacations for savvy travelers. While most members barely scratch the surface of program benefits, travel hackers dive deep into affiliate partnerships, elite status accelerators, and point transfer options to extract maximum value from points and miles.

A prime example - Chase Ultimate Rewards points earned on the Sapphire Reserve card. At face value through the Chase travel portal, they return around 1.5 cents per point towards paid travel. Decent but not amazing. However transfer those same points to airline and hotel partners opens up redemptions worth exponentially more.

60,000 Chase points could score a roundtrip economy ticket to Europe, getting about 1 cent per point in value. Transfer to United miles instead and you could fly roundtrip business class for the same 60k points - suddenly 5 cents per point in value. Transfer to Hyatt and you may enjoy multiple free nights in 5-star luxury accommodations for those same 60,000 points. Extracting outsized value takes more effort - you have to monitor award availability and points promotions closely. But the time invested pays back in hundreds of dollars in free travel.
Reddit users on channels like r/churning compile the latest tips and tricks to maximize points earned across programs. Superusers share experience with affiliate transfers, sweet spot redemptions, and combining point balances across household members. One user leveraged sign-up bonuses across player two cards and airline shopping portals to earn points for two free roundtrip business class tickets to Asia valued over $10,000.

Travel hacking blogs also uncover the best ways to extract value from points and elite status. Pat of the popular FlyerTalk boards distilled his wisdom into the book "Maximizing Elite Status & Free First Class Upgrades". He breaks down how choosing the right credit cards, playing programs off each other, and strategically planning travel unlocks thousands in free flights and upgrades. With a roadmap, achieving top-tier elite status faster means more free domestic first class seats and international business class upgrades.
While manufactured spending on welcome bonuses garners attention, true travel hackers know the big points hauls come from creative everyday efforts. Shopping portals, dining programs, and bonus category spend add up quickly. Transferring points between programs multiplies value exponentially. Being smart about what you earn and where you redeem makes all the difference.

It does require obsessing over programs like a part-time job. But services like Award Wallet track points balances and statuses across accounts in one dashboard. Point.Me shows the most valuable transfers between programs. AwardHacker maps sweet spot redemptions across partners. Tools exist to automate much of the manual work for you.