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Cheap Flights! ~$280 Winter in Puerto Rico, ~$522 to Japan, ~$582 to Thailand & Maldives, ~$396 to Panama

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    Via The Flight Deal, you can fly cheaply to Puerto Rico, Japan, Thailand and the Maldives, and Panama, from many US cities!

    Travel dates vary by destination, but most fares are for travel from Fall through December.

    If You’ve Ever Wanted to Visit Puerto Rico (or Japan, Thailand, or Panama), Here’s Your Chance!

    You can search for fares using ITA Matrix or Google Flights, then book them on the airline websites.

    I don’t know how long these fares will last!

    How to Book It

    Link:   ITA Matrix

    Link:   Google Flights

    Here’s how to use Google Flights to find sale dates.

    If you book a ticket with an online travel agency like Orbitz or Expedia, you may be eligible for a refund within a short time of booking your ticket.  Check out my post on cancellation policies for airlines and online travel agencies for more details!

    Chicago to Puerto Rico on American Airlines or United Airlines

    You can fly from Chicago to Puerto Rico on American Airlines or United Airlines for ~$280 round-trip.

    I was able to find flights in December on United Airlines for ~$285 round-trip.

    Trade Chicago’s Windy Winter for Warm Puerto Rico for ~$285 Round-Trip on United Airlines. Or Fly Even Cheaper in Autumn.

    The fare is available from September 2015 to May 2016, and requires a 21-day advance purchase.

    Note:  You can cancel a United Airlines reservation within 24 hours of booking and get a full refund.

    Remember, folks who have the Chase United MileagePlus Explorer card get a free checked bag.  But you have to use the card to pay for your ticket!

    Los Angeles to Japan on China Eastern

    Visit several cities in Japan from Los Angeles starting at ~$497 round-trip on China Eastern.

    With this deal, you can fly to:

    The most expensive flights are only ~$522 round-trip, which is still an amazing deal.

    I found a round-trip flight between Los Angeles and Nagasaki, Japan, in October for just ~$497!

    This fare is valid from August 29, 2015, to December 11, 2015.  You must purchase 1 day in advance of travel.

    Los Angeles to Thailand, Maldives, and More!

    The Flight Deal has the details on the incredible China Eastern fare sale to Asia from Los Angeles.

    Fly to Bangkok or Phuket, Thailand, for ~$593, Taipei, Taiwan for ~$587, Hong Kong for ~$586, or even the Maldives for ~$614!

    This fares will NOT last!  They are valid for travel from late August until December 11, 2015 and must be purchased at least 1 day in advance.

    San Francisco to Panama on Copa Airlines

    Visit Panama City for ~$400 round-trip from San Francisco on Copa Airlines.

    This fare appears to be valid until February 2016.

    I don’t know how long this will last, so book soon if you’re interested!

    Don’t Forget Southwest!

    Southwest also flies to Puerto Rico!  I checked the same dates from Chicago to Puerto Rico to compare prices, and Southwest is ~$347.

    But keep in mind, on Southwest everyone gets 2 free checked bags!  And your designated partner flies for nearly free when you have the Companion Pass.

    United Airlines passengers to Puerto Rico pay $25 for the 1st checked bag, and $35 for the 2nd.  So be sure to do the math and select the flights that are better for you!

    What If You’re Not in 1 of These Cities?

    Southwest – If you need more Southwest points, Chase Ultimate Rewards points transfer to Southwest.  Plus, if you have the Southwest Companion Pass, a friend can fly with you for (almost) free! British Airways – If you’re a short flight away from an included city, you can save miles by using British Airways Avios points to book an award flight on American Airlines, US Airways, and Alaska Airlines. Chase Ultimate Rewards points , American Express Membership Rewards points, and Starwood Preferred Guest points transfer to British Airways.

    Get Free Hotel Nights With These Cards

    Link:   Hot Deals – Hotel Credit Cards

    If you book a cheap flight, remember there are lots of ways to get cheap or free hotel rooms with points from credit card bonuses and spending!

    To find hotels that can be booked with points, I like using Hotel Hustle (which even shows you if rooms are actually available!) or AwardMapper.

    Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.

    After You Book Your Flight, Use Points for Free Stays at Hotels Such a Hilton

    Check out my posts on all the ways to earn Hilton and Hyatt points!

    Note:  Folks who want to book paid stays could check out discount sites like Orbitz, Expedia, or TravelPony for deals.  But remember you won’t get stay credits or points (and might not have your elite status recognized).

    An alternative is Airbnb.  It’s a great way to save money on accommodations, especially for longer stays.

    Read my tips on how to negotiate a better price on Airbnb!

    Bottom Line

    You can fly to Puerto Rico, Japan, Thailand and the Maldives, or Panama, from many US Cities!

    Travel dates and purchase requirements vary.

    You can fly to Asia (China, Japan, Thailand, Taiwan) from late August 2015 to December 11, 2015, to Puerto Rico from September 2015 to May 2016, and to Panama from late August 2015 until February 2016.

    Cheap fares like this won’t last long!  This is a terrific opportunity if you want to see more of the world on the cheap.

    But check fares on Southwest to Puerto Rico because they may be a better deal, depending on how many bags you want to take!

    Let me know if you book a ticket!

    Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)