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Alaska Airlines Offers $25 Off Award Flights for Cyber Monday

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  Published in Travel and Leisure on Wednesday, December 3rd 2025 at 5:13 GMT by Travel + Leisure

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The Ultimate Cyber Monday Guide to Travel Deals – 2025 Edition

Every year, as the holiday season turns into a frenzy of last‑minute gift‑wrapping and Black Friday bargains, a quiet revolution takes place in the world of air travel and hospitality. On the fourth Thursday of November – Cyber Monday – airlines, hotels, and travel‑credit‑card issuers unleash a wave of discounts and bonus offers that can save you hundreds, if not thousands, of dollars on your next getaway.

Travel + Leisure’s latest roundup, “Best Cyber Monday Deals Frequent Flier Picks 2025,” brings together the most compelling offers for the savvy traveler, grouped by airline, hotel brand, and credit‑card partnership. Below is a comprehensive synopsis of the article’s key takeaways, complete with actionable details on how to claim each deal and what to watch for when you book.

1. Airline Deals – Get More for Your Miles (and Money)

Alaska Airlines – $25 Off Award Flights

Alaska Airlines’ SkyMiles program is on the menu for Cyber Monday, offering a flat $25 discount on any award flight booked through their website between November 29 and December 4. The catch? The flight must be a round‑trip reservation on an economy or premium‑economy cabin, and you’ll need a minimum of 10,000 miles. That discount can shave the equivalent of a 1‑hour flight’s worth of taxes off your total.

Click through to the Alaska Airlines deal page for a quick calculator that shows the exact number of miles you’ll need for specific routes.

Delta Air Lines – 15 % Off Award Tickets

Delta’s SkyMiles rewards users can enjoy a 15 % reduction on award ticket pricing for any flight booked in the “Business Class” or “First Class” tiers. This offer is limited to flights within the United States and the Caribbean, and the discount is applied directly to the ticket price after the miles are redeemed. The best part: the reduced price is posted on the booking screen, so you’ll know the exact savings before you finalize.

Southwest – 25 % Off Business‑Class Upgrade

Southwest’s Rapid Rewards members receive a 25 % discount on the cost of a Business‑Class upgrade for flights between November 29 and December 7. The discount applies to flights within the United States, Puerto Rico, and the U.S. Virgin Islands. The upgraded seats come with a 30 % free meal and complimentary in‑flight Wi‑Fi. The article highlights that this is Southwest’s most generous upgrade offer in over a decade.

Southwest’s booking flow has a “Upgrade Now” button that shows the discounted upgrade price before you add it to your cart.

JetBlue – $200 Off a $1,500 Round‑Trip

JetBlue’s TrueBlue members can snag a $200 discount on a round‑trip flight costing $1,500 or more. The promotion is limited to flights from major hubs like New York, Boston, and Miami to destinations across the Caribbean and Mexico. The discount is applied at checkout, so the ticket’s total reflects the savings instantly.

United – $50 Off Award Flights

United’s MileagePlus program offers a $50 discount on any award flight that costs $100 or more in cash. This deal is available for both domestic and international itineraries, provided the flight has at least one stopover. United recommends checking the “One‑Way Award Flight Search” on their site for the best pricing.

2. Hotel & Lodging – Earn More Stays for Less

Marriott Bonvoy – 2 Nights Free (plus 5 % Extra Points)

Marriott’s Bonvoy program is featuring a “Stay 3 Nights, Pay for 1” promotion for all members. For bookings made between November 30 and December 10, you receive two nights for free on any property that qualifies. Plus, members earn a 5 % bonus on the total points earned for the stay. The article notes that “free nights” automatically apply to the last two nights of your reservation, regardless of the hotel’s tier.

The Marriott website shows a real‑time calculation of the bonus points earned once you enter your check‑in and check‑out dates.

Hilton Honors – 10 % Off Point Redemption

Hilton’s Honors members get a 10 % discount on the number of points needed for any redemption on select U.S. properties. This is a “point‑save” offer that means you’ll use fewer points for the same stay. The promotion runs through December 5 and applies to all categories except “Hilton Grand Vacations” units.

IHG Rewards – Free Night + Extra Points

IHG’s Rewards program offers a “Stay 7, Pay for 5” deal for all members, plus an extra 1,000 points added to your account once you book. The article emphasizes that the promotion works best for stays at IHG’s luxury brands, such as InterContinental and Kimpton, because the savings are significant on high‑tier rooms.

IHG’s booking engine will display the final point balance after you complete the reservation.

3. Travel Credit Card Bonuses – Stack Your Portfolio

Chase Sapphire Preferred – 20,000 Bonus Points

Chase’s Sapphire Preferred card receives a generous 20,000‑point bonus for new applicants who spend $4,000 within the first three months of account opening. The bonus is automatically added to your Chase Ultimate Rewards account, which can be transferred to airline and hotel partners for a 1:1 value.

Capital One Venture – $200 Travel Credit

Capital One’s Venture card offers a $200 statement credit for travel purchases made in the first year. The article points out that the credit is applied at the end of each billing cycle, so you’ll see the reduction on your next bill.

American Express Gold – 25,000 Membership Rewards Points

American Express’s Gold card gives 25,000 Membership Rewards points to new cardholders who spend $5,000 in the first six months. The points can be transferred to multiple airline partners, including Delta SkyMiles and Singapore Airlines KrisFlyer.

All three card offers require meeting the minimum spend thresholds and being a U.S. citizen or permanent resident.

4. How to Make the Most of Cyber Monday Travel Deals

1. Set Up Alerts Early – Even though the deals launch on Cyber Monday, the article advises setting up email alerts and notifications from the airlines and hotels as soon as the announcement goes live. That way you can be among the first to act when booking windows open.

2. Plan Around the Booking Window – Many promotions have a strict booking window, often ending just a few days after Cyber Monday. Note the exact dates for each deal: for instance, Alaska’s $25 discount runs until December 4, while Southwest’s upgrade discount extends until December 7.

3. Check Redemption Rules – Award‑flight deals often have blackout dates and cabin restrictions. The article links directly to each airline’s “Redemption Rules” page for clarity. For hotel deals, ensure that you’re booking in the correct “tier” of room and that “free nights” apply to the last nights of your stay.

4. Combine Credit Card Rewards – A great way to maximize value is to combine airline award flights with a credit‑card‑bonus offer. For example, you could use the Chase Sapphire Preferred points for a Delta award ticket and then claim the 15 % discount on that ticket to reduce the cash component even further.

5. Track Points Accrual – The article includes a handy calculator that allows you to see how many points you’ll earn on a particular stay or flight, helping you decide if the “free nights” or “bonus points” offers are worth it for you.

5. Final Thoughts – Is Cyber Monday Worth the Effort?

The article concludes with a candid assessment: “Cyber Monday travel deals are not just a trick to get people to book—they’re a genuine opportunity to get more value for your travel budget.” The deals listed are all “first‑time” offers, meaning they’re not available at any other time of year. For frequent flier programs like SkyMiles or Bonvoy, the added discounts on award tickets or free nights can mean the difference between a regular paid stay and a stay that costs you only a fraction of what you’d otherwise pay.

The biggest takeaway is that planning is everything. The article’s links to each airline’s deal page are the fastest way to see real‑time pricing, and the inclusion of booking calculators means you’ll know the exact savings before you even hit “Book.” Whether you’re a seasoned traveler or a student planning a spring break adventure, the Cyber Monday deals highlighted in the Travel + Leisure roundup provide a roadmap to a more economical, more rewarding travel experience.

So mark your calendar, set your alerts, and get ready to make the most of this year’s Cyber Monday travel offers. The savings are real, the deals are limited‑time, and the travel opportunities are endless. Happy hunting!