Cheap Award Flights to the 17 Best Places to Go in 2026: A Month-by-Month Deal Calendar

Cheap Award Flights to the 17 Best Places to Go in 2026: A Month-by-Month Deal Calendar

Hook: You’re sitting on points and miles, but rising fares, confusing award rules and shifting availability have you paralyzed. This guide turns that chaos into a clear, month-by-month award calendar for the 17 destinations The Points Guy highlighted for 2026 — showing the cheapest months to fly, the typical award windows you’ll see, and which frequent-flyer programs and transferable points are most likely to snag you a cheap award seat.

“Make 2026 the year you stop hoarding points for ‘someday’ and book that trip.” — The Points Guy (Jan. 16, 2026)

Use this as an operational playbook. At the top of the article are the most important, time-sensitive tactics. Scroll down for the destination-by-destination calendar with practical booking moves you can act on today.

Quick overview — what changed in 2026 and why it matters for award shoppers

• Dynamic award pricing is now mainstream. More carriers continue to move away from fixed “saver” inventory toward revenue-based award seats. That means search flexibility, shopping multiple programs and timing your transfers are more important than ever.
• Route restorations and new nonstops (late 2025 — early 2026) increased seat supply to popular regions. More supply = more award seats overall, especially in shoulder seasons.
• Transfer ecosystem is stable but competitive. Bank currencies (Amex Membership Rewards, Chase Ultimate Rewards, Capital One Miles, Citi ThankYou) still move to most useful partner programs — but transfer bonuses are now strategic events rather than routine.
• Last-minute award openings are common. Expect both early-calendar releases (330–365 days out) and late-seat drops 2–6 weeks before departure, especially on long-haul and premium cabins. If you build a quick monitoring tool you can catch those drops — see a short micro-app playbook for alerts and simple automations.

How to use this calendar (three simple rules)

1. Search broad, then narrow: Start with alliance-wide searches (Star Alliance / oneworld / SkyTeam) and add program-specific searches once you find dates with inventory.
2. Hold transferable points until you have a confirmed award: transferable points are typically irreversible and transfer bonuses change. Don’t move bank points until you can book or have a very short booking window.
3. Mix long and short windows: Look at both the early schedule release window (around 330–365 days out) and the last-minute window (2–6 weeks before): both produce cheap award opportunities in 2026.

Legend: what I mean by “award availability windows”

• Early release (330–365 days out): Most legacy carriers still post inventory when schedules open. Good for planning.
• Saver bumps (6–12 months out): Some carriers release additional saver seats during the 6–12 month window, often for shoulder season dates.
• Promo releases (1–3 months out): Carriers with promo awards (Flying Blue, Qantas, others) often publish discounted award seats close to departure.
• Last-minute drops (2–6 weeks out): Airlines sometimes open unsold paid inventory to award booking close to departure — a prime target if you’re flexible.

Transfer partners shorthand

Throughout the destination notes I recommend programs by name; if you rely on transferrable bank points, remember these four currencies are the backbone of award flexibility in 2026:

• American Express Membership Rewards
• Chase Ultimate Rewards
• Capital One Miles
• Citi ThankYou Points

Each currency supports a slightly different set of airline partners — always check current transfer partners and transfer ratios before moving points. If you want to evaluate booking channels vs direct-booking, read up on direct booking vs OTAs to decide whether to use an aggregator or book direct with a partner program.

Month-by-month framing (high level)

Below is a one-line summary of where to look each month — use it as a search plan. Then you’ll find the 17 destination breakdowns with specific award availability windows and program suggestions.

• January–February: Southern-hemisphere bargains (Cape Town, Buenos Aires) and off-season Europe (Athens shoulder deals).
• March–April: Early spring Europe (Lisbon, Dublin) and Japan shoulder season (Kyoto).
• May–June: Pre-summer transatlantic value and Central America (Costa Rica, Mexico City) before peak pricing hits.
• July–August: Peak season — target last-minute drops and premium-cabin upgrades with points.
• September–October: Europe shoulder season (Santorini/Dubrovnik/Athens) and excellent availability to Iceland/Scandinavia for Northern Lights/Nature trips.
• November–December: Holiday premium fares spike; look for promo awards, Thanksgiving and Christmas require early booking (330+ days out).

TPG’s 17 destinations — cheapest months, award windows and best programs

For each city below: Cheapest months lists when paid fares and awards are usually cheapest. Award availability windows shows typical times you’ll find seats. The Best programs section explains where to search first and which transferrable currencies give you flexibility.

1) Kyoto, Japan

• Cheapest months: March–April (cherry blossom shoulder), November (autumn color) — avoid Golden Week.
• Award availability windows: Early release at 330–365 days; additional saver inventory 6–3 months out; occasional last-minute premium drops 3–6 weeks out.
• Best programs & transfer partners: Look to Star Alliance carriers and partner programs for the best routing flexibility. Consider programs that book long-haul JAL/ANA space (search award calendars on carrier sites and major partners). Use transferable banks to convert into the program you need only after confirming availability.
• Booking strategy: If you want a specific date in cherry-blossom or autumn weeks, book at schedule release. Otherwise hunt 2–3 months out for shoulder-season saver seats.

2) Lisbon, Portugal

• Cheapest months: November–February (excluding Christmas/New Year), and late spring (May).
• Award availability windows: Plenty at 6–12 months out thanks to boosted transatlantic capacity (new nonstops announced in late 2025); also look for last-minute promo awards from European partners.
• Best programs & transfer partners: Avios-linked programs are handy for short-haul add-ons and transatlantic seasonal routes; Star Alliance award searches and Flying Blue promo offers can yield savings. Transferable bank points give you multiple routing options.
• Booking strategy: Book non-holiday dates at schedule release; use Flying Blue and Avios deals for flexible short trips.

3) Reykjavik, Iceland

• Cheapest months: October–November and February–March (shoulder-season discounts and cheaper hotels).
• Award availability windows: 6–12 months out for seasonal schedules; look for last-minute off-peak seats 1–2 months out when airlines run fare sales.
• Best programs & transfer partners: Avios-style redemptions (short-haul advantage), plus Star Alliance and oneworld when carriers operate Reykjavik routes. Transferable points let you pivot between whatever partner shows the space.
• Booking strategy: Be flexible on airports (KEF vs. nearby) and use short-haul award sweet spots to reduce mileage cost.

4) Mexico City, Mexico

• Cheapest months: May and September–October (shoulder and post-summer lull).
• Award availability windows: Good inventory at 330+ days and again in the 60–120 day window; domestic carriers often release saver seats closer in.
• Best programs & transfer partners: Look at oneworld and SkyTeam partners depending on your origin; U.S. domestic carriers’ award seats (if flying AA or Delta) can be easiest with airline credit cards; transferable points add flexibility when partner awards open.
• Booking strategy: Book major holidays early; otherwise you can often find midweek departures at lower mileage prices.

5) Cartagena, Colombia

• Cheapest months: April–May and September–October (shoulder seasons avoiding peak winter demand).
• Award availability windows: Best 3–9 months out with occasional last-minute openings; regional carriers may open seats closer in.
• Best programs & transfer partners: Consider Star Alliance and oneworld partners for the best routings. Transferable points are useful if you need to jump between partner programs.
• Booking strategy: If you’re flexible on route (Bogotá + local connection vs direct), you can often cut mileage costs substantially.

6) Athens, Greece

• Cheapest months: Late October–early November and March–April (shoulder seasons with comfortable weather).
• Award availability windows: 330–365 days out for peak summer; excellent shoulder-season availability 3–6 months out.
• Best programs & transfer partners: Flying Blue and Avios programs often show good transatlantic options; Star Alliance partners also competitive. Transferable bank points provide the most program choices.
• Booking strategy: For summer travel, aim at schedule release; for autumn/spring, hunt bargains 1–4 months out.

7) Marrakech, Morocco

• Cheapest months: May and October–November (milder weather and lower demand).
• Award availability windows: 3–9 months out for European connections; watch for last-minute promo awards from European programs.
• Best programs & transfer partners: Airlines that connect through European hubs (on the Avios network and Flying Blue) are often cheapest in points. Use transferable currencies to pivot into those partners as needed.
• Booking strategy: Search multi-carrier options — sometimes a European carrier award to Marrakech plus a separate low-cost connection is the best use of miles.

8) Vancouver, Canada

• Cheapest months: January–March and late October (off-peak winter and shoulder season).
• Award availability windows: Domestic award availability tends to open early (330 days) and again nearer travel; transborder partner seats sometimes appear in last-minute windows.
• Best programs & transfer partners: Consider programs that book North American transborder flights efficiently. Airline loyalty cards for the carrier you prefer can be a quick path to booking if inventory is limited.
• Booking strategy: Redeem on midweek flights and avoid holiday windows unless you book far ahead.

9) Cape Town, South Africa

• Cheapest months: May–August (South African winter, lower demand) and February–March.
• Award availability windows: Long-haul award seats are often released at schedule opening (330+ days) and again 6–12 weeks before departure; premium-cabin seats can be scarce.
• Best programs & transfer partners: Star Alliance and SkyTeam partner awards often give best routings. Transferable bank points allow flexibility across alliances.
• Booking strategy: For premium seats, be aggressive at schedule release. For economy, watch 2–3 month windows for price drops and promos.

10) Seoul, South Korea

• Cheapest months: Late March–May (spring), and October–November (autumn shoulder).
• Award availability windows: Early release (330–365 days) is reliable; additional saver seats 2–6 months out, with last-minute premium openings occasionally.
• Best programs & transfer partners: Programs that book Korean Air / Asiana space and Star Alliance redemption routes are valuable. Transferable points let you shift between the few programs that access that inventory.
• Booking strategy: Book your desired cabin/city at schedule release if traveling in spring foliage windows.

11) Sydney, Australia

• Cheapest months: February–March and September–November (shoulder seasons and after the Aussie summer holidays).
• Award availability windows: Long-haul award inventory is posted at schedule release but premium seats are best captured early or in last-minute drops.
• Best programs & transfer partners: Programs that book direct long-haul partners (and alliances that serve transpacific markets) are essential. Transferable bank points are useful but confirm seat availability before transferring.
• Booking strategy: For premium cabins, book at 330–365 days out; economy travelers can often find saver seats 2–4 months out in shoulder seasons.

12) Buenos Aires, Argentina

• Cheapest months: March–May and September–November (shoulder seasons on either side of Southern Hemisphere summer).
• Award availability windows: Best at 6–12 months for peak dates; look for domestic/regional partner inventory closer in.
• Best programs & transfer partners: Star Alliance and oneworld carriers that fly to South America are your best bets; transferable points that support both alliances increase odds of a low-mileage booking.
• Booking strategy: Avoid Argentina’s holiday weeks unless you book very early; otherwise the shoulder seasons reward flexibility.

13) San José, Costa Rica

• Cheapest months: March–May and September–November (shoulder seasons excluding major holidays).
• Award availability windows: Good inventory 3–9 months out; domestic/regional partner seats sometimes released closer in.
• Best programs & transfer partners: oneworld and Star Alliance partners that fly Central America routes; transferable points provide routing flexibility and the ability to book on carriers with lower surcharges.
• Booking strategy: For beach travel, flexible dates mean you can pick up last-minute award deals in the 6–8 week window.

14) Dublin, Ireland

• Cheapest months: November–February (off-peak) and April–May (shoulder).
• Award availability windows: Early release (330+ days) and frequent last-minute promo awards from European carriers in the 1–3 month window.
• Best programs & transfer partners: Programs that use Avios and Flying Blue mechanics are especially useful. Transferable points allow you to take advantage of carrier-specific promos.
• Booking strategy: Watch for European carrier promo reward sales; transferable points let you pounce fast when they appear.

15) Dubrovnik, Croatia

• Cheapest months: May and September–October (before and after peak summer crowds).
• Award availability windows: Best in shoulder season 2–6 months out; summer often requires booking at schedule release.
• Best programs & transfer partners: European partner programs and Star Alliance routes via hubs give best award access. Transferable points to Flying Blue/Avios help with short-hop routing.
• Booking strategy: Dubrovnik’s peak summer demand means you should decide early for June–August travel; otherwise target late-spring for better award odds.

16) Oslo, Norway

• Cheapest months: November–March (off-peak winter) and late September (shoulder).
• Award availability windows: Good at schedule release and often in the 2–3 month out promo window for European carriers.
• Best programs & transfer partners: Avios/Flying Blue and Star Alliance partners for Nordic routings. Transferable points broaden your booking options among those programs.
• Booking strategy: Leverage short-haul Avios sweet spots to save miles on intra-Europe legs.

17) Cairo, Egypt

• Cheapest months: March–May and October–November (comfortable weather, off-peak pricing).
• Award availability windows: 3–9 months out for main routes; seasonal carriers and connections can release seats closer in.
• Best programs & transfer partners: oneworld and Star Alliance carriers that route through European/Middle Eastern hubs. Transferable points are useful for accessing advantage routing with lower surcharges.
• Booking strategy: Mix-and-match partners for routing; consider routing via European hubs to cut mileage and fees. For a primer on whether to use aggregator channels or go direct to partners, see direct booking vs OTAs.

Concrete search checklist — what to do today

1. Pick three target dates per destination: one in the early-release window (330+ days), one 3–6 months out, and one last-minute (2–6 weeks). Search all three.
2. Search multiple programs up front: Don’t just search your go-to airline. Use award search tools for each alliance and program noted above — and consider a simple offline-capable tool to store screenshots and confirmations (offline-first tools).
3. Set alerts and track fares: Use an award alert service and set paid-fare alerts — sometimes cheap paid fares + points-for-upgrades yield better value than stingy award space. If you want to build or customise alerts, a short micro-app playbook can get you live quickly (7-day micro-app).
4. Hold points, then transfer: Confirm an award bookable with miles before transferring bank points. If a transfer bonus lines up with availability, jump.
5. Be ready to jump on last-minute drops: Keep transferable balances liquid and bookmarks for partner booking pages. If you want to automate monitoring, check micro-app templates and alert patterns for inspiration (micro-app templates).

Advanced strategies for 2026 (what the pros are doing)

• Mix award + cash for upgrades: Book economy award seats early, then bid for or pay to upgrade later when premium cabin cash fares lag. For a quick guide on channel choices, see the direct vs OTAs comparison.
• Exploit transfer bonuses: Transfer-bonus windows are rarer but still powerful. If a partner shows availability, a small transfer bonus (10–30%) can make a big difference.
• Use regional hubs as gateways: Book into a major hub with saver space, then use local low-cost carriers (cash) for the final leg if award rates are poor.
• Stagger multi-destination trips: Book the most constrained leg (holiday/peak dates) first, then add flexible legs to save miles.

Common pitfalls and how to avoid them

• Transferring too early: If you transfer to a program without a confirmed booking, you can lose flexibility — and with automation and trust changing how offers are delivered, that risk is higher.
• Ignoring carrier surcharges: Some partners levy heavy fuel surcharges; always check total out-of-pocket before booking.
• Overreliance on one program: Spread risk by keeping points in at least two transferable currencies or one transferable currency + one airline program.

Final takeaways (the inverted pyramid: most important first)

• Plan for both early and last-minute award windows. 330–365 days out captures schedule-release inventory; 2–6 weeks out often yields last-minute gems.
• Use transferable points as a tool, not a trap. Keep them until you can book or until a clear transfer-bonus opportunity appears.
• Hunt shoulder seasons for the cheapest months to travel. The calendar above shows the best monthly windows for each TPG destination to maximize award value.

Call to action

Ready to book? Start by picking your top two destinations from this calendar, set award alerts, and sign up for calendar-release notifications (330-day windows). If you want help matching your point balances to a specific trip, use our free point-matching tool or get an email alert when a transfer bonus aligns with confirmed award space. Don’t hoard — plan and book.

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