Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They’re Gone

Post originally Published December 26, 2023 || Last Updated December 26, 2023

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Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Last Minute Winter Escape Deals Still Available


Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They’re Gone

Even though we're already well into winter, there are still some killer last minute deals up for grabs if you want to escape the cold and dreary weather. While peak holiday travel season may be over, savvy travelers know that January and February can offer just as many money-saving opportunities, without the crowds.

For warm weather chasers, destinations across Mexico, the Caribbean, and Central America continue to have enticing offers well after New Year's. I recently stumbled upon roundtrip flights from Chicago to Cancun for only $198, an absolute steal. The same goes for beach locales like Puerto Vallarta, Punta Cana, and Montego Bay, where flights are routinely popping up in the $200-$300 range. Even further south, flights to Costa Rica and Panama remain extremely affordable, often dipping below $250 roundtrip from major US cities.
Of course, just because it's winter doesn't mean you have to stick to strictly beach vacations. There are also fantastic last minute deals to be had for urban getaways, particularly with travel to Europe being slower this time of year. I've seen roundtrips to Madrid, Barcelona, Amsterdam, and Prague going for $350 or less pretty consistently. Ditto for flights to Tokyo, Seoul, Singapore, and other Asian megacities, where airfare from the West Coast can drop below $500 roundtrip.

The best part? Once you lock in cheap flights, hotels are also drastically discounted, even at top properties. I'm talking luxury 5 star resorts in Mexico and the Caribbean advertised 30-40% off. Swanky hotels in Amsterdam and Lisbon for under $150/night. It's truly an ideal time for budget-conscious luxury travelers to indulge.
Of course, flexibility is key if you want to score these last minute winter escape deals. Being open to flying midweek instead of weekends makes a huge difference in finding lower fares. As does looking at alternative airports - flying into New York's JFK instead of LGA, or Washington Dulles instead of DCA.

But for those with pliable travel dates, the rewards are well worth it. And unlike the chaos of holiday season travel, you're way more likely to smoothly sail through airports without the usual headaches. Just be sure to pounce when you see a good fare, as the most rock bottom deals get snatched up quickly even in winter.

What else is in this post?

  1. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Last Minute Winter Escape Deals Still Available
  2. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Use Points for Dream Vacations Before Award Chart Changes
  3. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Money Saving Hacks to Unlock Deep Travel Discounts
  4. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Insider Tips to Find Cheapest Airfares This Month
  5. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - New Hotel and Resort Openings to Book for 2023
  6. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Under the Radar Destinations Offering Big Savings
  7. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Maximize Credit Card Rewards for Free Flights This Year
  8. Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Stretch Your Budget Further with Shoulder Season Trips

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Use Points for Dream Vacations Before Award Chart Changes


For frequent flyer fanatics, one thing is constant: airline loyalty programs love to devalue their award charts. Just when you've stockpiled enough miles for that coveted first class ticket to Bora Bora, the airline ups the ante and requires more points for the same award. It's a frustrating cycle, but also a reminder to use your hard-earned points strategically before they lose value.

A prime example is the recent United MileagePlus changes that kicked in early this year. Popular premium cabin awards to Hawaii, Europe, and Asia all saw point increases of up to 33% with no prior warning. Similarly, back in 2016 American AAdvantage eliminated their discounted MileSAAver awards which was a slap in the face to loyal elites. And we don't even have to mention the drastic devaluations that programs like Delta SkyMiles and British Airways Avios seem to roll out annually.

The best defense? Use those miles for aspirational bucket list trips before the next program overhaul hits. Instead of hoarding points indefinitely, set your sights on that overwater villa vacation in the Maldives, or splurge for an intimate safari lodge in South Africa. Even if an award chart stays stable for years, inflation means your points lose buying power over time. And you never know when a surprise devaluation will strike.
Of course redemption sweet spots still exist, like using United miles for Lufthansa first class, or Japanese programs like ANA Mileage Club and JAL Mileage Bank which continue to offer strong value on partner awards. But when it comes to your most coveted dream trips, book sooner than later. Waiting too long is a gamble that could leave your points worth far less down the road.
And before spending hard-earned points, always compare cash fares as a baseline. Dynamic pricing means it’s not unheard of to find business class flights for under $2,000 to Europe and Asia, or lie-flat seats to Hawaii for $600. In those cases paying cash makes more sense than redeeming your precious rewards. But for tickets that would otherwise cost $5k, $10k, or even higher, that's when points shine.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Money Saving Hacks to Unlock Deep Travel Discounts


While shopping around is always key to finding travel deals, veteran wanderers know that true rock bottom prices take some creative sleuthing. From leveraging little-known airline perks to hacking hotel loyalty programs, you can uncover savings that aren’t visible at first glance.

One of my all-time favorite tricks is utilizing airline status matches to score elite benefits on the cheap. By requesting a fast-track status challenge with a competitor, you can unlock perks like seat upgrades, checked bag waivers, and airport lounge access for just a few flights. I’ve used programs like American’s Status Challenge and Delta’s Crossover Rewards to temporarily score Gold or Platinum elite status without actually earning it through expensive travel.

Speaking of elite status, many travelers overlook leveraging hotel loyalty programs for major discounts. Simply by holding mid-tier elite status, you can get 20% or more lopped off room rates. And it’s surprisingly easy to earn basic status like Marriott Silver Elite or World of Hyatt Discoverist which unlocks real savings. Far cheaper than paying rack rates if you stay at a brand frequently.

When it comes to prepaid hotel rates, always check both the hotel website and OTA sites like Expedia - whoever has the lowest price wins. For added savings, use a cash back portal like Rakuten to double dip and earn percentages back. The same goes for rental cars - always compare rates amongst different aggregators and apply coupons when available.

Of course, timing your travel strategically around seasons and holidays is also key to unlocking unpublished discounts. Booking summer vacations in April-May or fall getaways in August-September opens up last minute deals as demand softens. The same goes for traveling right after peak holidays when both airfare and hotels take a dive. Being flexible with your dates is critical to uncovering the lowest fares.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Insider Tips to Find Cheapest Airfares This Month


Finding airfare deals takes insider knowledge - especially when aiming to travel on a budget. As an obsessive flight deal hunter, I've compiled my top tips for unlocking the cheapest flights this month.

First, flexibility is absolutely essential to get the lowest fares. Most travelers have a range of dates that could work for an upcoming trip. Being open to flying midweek, shoulder season, or with a long layover opens up deals that may be $200+ cheaper than peak days. I recently helped my friend Jason snag a roundtrip fare from LA to Barcelona for only $329 by tweaking his dates slightly outside of summer season.

Second, learn how to best utilize airline sales calendars and fare alerts. Most airlines run weekly or monthly sales on select routes which aren’t heavily advertised outside their email lists. Sign up for updates from budget carriers like Spirit, Frontier and Allegiant which offer rock bottom fares during promotions. I also love checking Air France’s weekly deals – I recently spotted roundtrip flights from several U.S. cities to Paris for under $300.
Leveraging airfare prediction tools like Hopper and Google Flights is another must. Their algorithms analyze historical data to forecast when prices may drop. This helps you pounce when airfare dips on your target routes. I always check Hopper’s “Price Freeze” option which lets you lock in a fare now and rebook later if it drops.

Don’t forget to check alternate airports too. Flying into Chicago Midway instead of O’Hare, or Washington Dulles instead of Reagan National can unlock major savings. Nearby airports often have drastically different fares so expand your search radius.

Being open to basic economy and no-frills airlines (as long as you pack light!) is another huge money saver. I recently flew basic economy to Hawaii for only $278 roundtrip - an absolute steal. Just pack smartly to avoid steep fees.
Timing it right saves big. Look for deals in the typical “dead zones” of January, August/September, and right after major holidays when prices plummet across the board. Just be ready to pounce when deals emerge.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - New Hotel and Resort Openings to Book for 2023


Among avid travelers, there's always a thrill in being one of the first guests to experience a hot new hotel opening. In 2023, an array of tantalizing properties are set to throw open their doors in coveted destinations worldwide - giving you bragging rights for sampling them early.

At the top of every beach lover's list is the all-new Ritz-Carlton Maldives opening in May 2023. Boasting 150 villas, several restaurants led by Michelin-starred chefs, and a one-of-a-kind underwater gallery, it promises next-level luxury. CNN Traveler editor Stacey Lastoe says, "I've been eagerly awaiting the opening of this resort. The overwater villas look absolutely incredible with private freshwater pools and slide-outs that allow guests to be fully immersed in the turquoise lagoon. This is going to raise the bar in the Maldives."

In Europe, Madrid will welcome the dazzling Six Senses Madrid in Summer 2023 located in the city's historic Triangle de Oro. With just 45 rooms decked out in chic Spanish style, a rooftop bar overlooking the Madrid skyline, and an Alchemy Bar specializing in artisanal cocktails, Six Senses is bringing five-star boutique opulence to the Spanish capital.

Outdoorsy types will want to flock to 1 Hotel San Francisco when it opens in late 2023. Perched on the Embarcadero with stunning bay views, this eco-friendly property promises to be a sustainable oasis with four acres of outdoor space and regional design touches. 1 Hotels has earned a reputation for their dedication to environmentalism, making this a great call for the eco-conscious.
Also slated for 2023 is the show-stopping Planet Hollywood Cancun which brings an all-inclusive beachfront experience, 10 restaurants from celebrity chefs like Guy Fieri, and star-studded memorabilia to the Mexican Caribbean. For film buffs, it's a chance to vacation like an A-list celeb.
Of course beach resorts reign supreme, but city hotels have equally enticing openings on the horizon. These include the W Rome which will bring the brand's signature cool factor to the Eternal City, the Mandarin Oriental Tokyo, and the Langham Gold Coast in Australia.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Under the Radar Destinations Offering Big Savings


Savvy travelers know that flying under the radar often unlocks the biggest travel savings. While popular destinations drown in crowds and inflated prices, venturing just slightly off the beaten path can unlock memorable experiences without exhausting your budget. Here are four under-appreciated destinations offering tremendous value in 2023.
Budapest has emerged as the affordable alternative to overtouristed Prague and Vienna. Hungary's elegant capital dazzles with medieval castles, thermal baths, and the continent's most stunning parliament building lining the Danube River. Roundtrip flights from the U.S. hover around $800, and you can stay at design-forward hotels like the Aria Hotel for less than $200. One of Europe's best restaurant and bar scenes means you can dine on goulash and knock back Unicum spirits without draining your wallet.

Nature lovers are flocking to Ecuador, where the diversity of landscapes allows you to go from the Amazon jungle to snow-capped volcanoes in just a few hours. Flights from North America can dip below $400 roundtrip when snagged during sales. Once there, you can stay in Quito's new design hotels for around $70-100 nightly. Splurging on once-in-a-lifetime wildlife experiences in the Galapagos Islands and cloud forests rarely exceeds $300 per day.
For beach bums on a budget, it's hard to beat Southern Portugal. Picturesque towns like Lagos and Sines remain tourist-free and affordable compared to overheated Lisbon. Expect roundtrip airfare around $900, then snag hotels steps from stunning cliffs and sandy coves for less than $100 per night. Indulge in fresh seafood and vinho verde, hike dramatic coastal trails, and relax on empty stretches of the Algarve.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Maximize Credit Card Rewards for Free Flights This Year


Strategically maximizing credit card points has saved me thousands on travel over the years. As an obsessive deal hunter, I'm always looking for ways to extract maximum value from sign-up bonuses, category bonuses, and everyday spending.

The key is treating points like cash. Just like you would diligently invest money, you have to be equally calculated in accruing and redeeming rewards. Simply letting points accumulate in your account is wasting potential value. With the right strategy, you can unlock astronomical travel perks.
I advise keeping a spreadsheet of all your cards along with their annual fees, bonus categories, and accrued points. Track when you last earned a sign-up bonus on each card - most programs won't let you collect again for 24 months or more. Note annual bonus cycles like Chase and Amex which reset each cardmember year.

Before any big purchase, check which card maximizes rewards for that category. I put all advertising spend on my Citi Premier for 3x back, while using Chase Ink for 5x on internet and cable bills. Even middling category spend adds up fast.

Always use shopping portals when available to double dip on rewards. I book rental cars through Amex's site for extra points on top of what my card earns. When your points stash gets big enough, transfer to hotel and airline partners for maximum redemption value. I transfer Amex MR to Virgin Atlantic to book Delta flights with low fees, and Chase UR to Hyatt for luxury hotel stays.

Redeeming points directly via your card's travel portal often means settling for lower value. I cringe when I see friends booking directly through Capital One Travel at half the value transfer partners offer.

Timing is also essential. I try to book at least 6-8 months out for peak season flights, and look for airfare sales 11-12 months out. Long-haul business class tickets are especially scarce close-in. Prioritize your aspirational bucket list trips first when airline award space is most wide open.

Finally, don't leave points on the table by carrying a balance or interest charges from month to month - that's just negating any rewards you earn. Same goes for paying annual fees on cards you rarely use. I cancel cards that no longer make financial sense unless they're my oldest for credit score purposes.

Travel Tuesday 2023: Snag the Hottest Flight and Hotel Deals Before They're Gone - Stretch Your Budget Further with Shoulder Season Trips


The savviest travelers know that visiting destinations during shoulder season unlocks big savings compared to peak holiday dates. By strategically targeting the sweet spot between high and low season, you can stretch your budget much further without sacrificing experience. Here’s why it pays to book shoulder season vacations this year.
Shoulder season differs for every destination, falling between the overcrowded summer months and the quieter winter lull. In Europe, May and September offer mild weather, smaller crowds, and abundant hotel availability before the crush of August. I recently scored flights from New York to Barcelona for only $350 roundtrip traveling in late September, easily half the cost of July.

The same goes for perennially popular U.S. getaways like Hawaii, Florida, and national parks. Visiting right before or after summer vacations end means you’ll still enjoy warm weather without battling hordes of tourists. Fly into Maui in May or September and you can snap up oceanfront resorts for 30-40% off peak rates. Visit Orlando in October when theme park crowds thin dramatically.

Shoulder season also brings savings for cultural urban escapes. Cities like Paris, Amsterdam, and Rome remain pleasant in spring and fall without summer’s endless lines. You’ll breeze right into galleries and museums that are stuffed to the gills during July and August. Restaurants and cafes recapture their intimate charms too after the visitor onslaught abates.
The travel industry temptation to oversimplify seasons into binary “high” and “low” categories overlooks the nuances that shoulder seasons provide. Sure you can visit Paris in January for rock bottom fares, but limited sunlight and closures mute the experience. Or economically tour Egypt in the scorching heat of August, but good luck enjoying much time outside.

By targeting shoulder weeks around peak season, you get the best of both worlds - decent weather, open attractions, lower prices. Once crowds dissipate, hotels and tour operators are much more amendable to offering promotions and discounts to fill remaining inventory too.

Avoiding school holidays is key to maximizing shoulder season savings. While spring break, summer vacation, and holidays like Easter always command premium rates, traveling just before or after means still enjoyable weather without the humidity of true peak season.

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