Travel Hacking 101: 9 Critical Tips to Know

by | Last updated Sep 4, 2023 | Travel Hacking

Travel hacking 101. Sounds complicated, but it’s not. With a couple of a few pointers, you will be well on your way to earning points and miles to cash in on free flights and hotels. Suddenly that 2-week trip to Africa or exotic vacation to the Maldives becomes obtainable. No more dreaming. I will warn you though travel hacking can become addicting and super thrilling when you score that amazing redemption.

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What is travel hacking?

Travel hacking refers to using travel credit cards and airline miles to collect points, so you can cash them out on free flights and hotels, upgrades, airport lounge access, and other perks.

Where do you even begin?

There are many advanced techniques, but these are the 9 steps to get you well on your way to free travel. Let’s dive in.

01- Pick an Airline Alliance & Stay Loyal

American airlines airplane

American Airlines plane



What you need to know is there are 3 airline alliances:

  • Star Alliance
  • SkyTeam
  • Oneworld

An airline alliance is a group of partner airlines that span the entire world. If you have status on one airline, then its partner airlines will also recognize you and give you priority treatment.

Pick one alliance, and stick with it for 2 reasons.


    #1- Free Flights

    The miles you accumulate can be redeemed for free flights. The number of miles needed for that free flight will vary based on the destination and the fare class you want (economy, business, first-class).

    Flying is not the only way you obtain airline miles. You can also transfer your Chase and American Express credit card points into airline miles.

    Another way to obtain airline miles quickly is by signing up for a big bonus offer with an airline co-branded credit card.

    For example, the United Explorer card offers 50,000 United bonus miles after spending $3,000 in the first 3 months your account is open.


    #2- Airline Perks

    As you accumulate points and gain status, the airline’s loyalty program will usually award you with perks like free checked bags, priority boarding, and lounge access.

    * Note, not every airline is part of an alliance. For example, Southwest is not in an alliance.



    This will depend on 2 factors: 


    #1- Home Airport

    What major airlines are at your home airport? This really is the main determining factor.

    Do you live in Atlanta, Georgia? You will probably pick Delta.

    What about Chicago, Illinois? You are probably going with United.

    How about Charlotte, North Carolina? American Airlines will likely be your top pick.


    #2- Where You Like to Travel

    Where do you like to travel? Europe? U.S.? Asia?

    Which airlines fly to your desired travel destinations? If you only fly domestically or maybe to the Caribbean every now and then, you might not pick an alliance and just stick with Southwest. Your travel goals will help guide this decision.

    If you live in the United States, your major airline choices are as follows:

    1. United (Star Alliance)
    2. Delta (SkyTeam Alliance)
    3. American (Oneworld Alliance)


    Once you select your alliance, make sure to SIGN UP with your airline’s loyalty program and add that number to EVERY flight you book. 

    An airline alliance is like a marriage. For better or worse, you are in it. Make sure it is a good one and meets your needs, and you will be rewarded for that loyalty. 

    PRO TIP: Go to Wikipedia and type in your home airport. It will show all the main airline carriers and the main destinations. Use this information to determine your airline alliance.



    Cathay Pacific The Wing Lounge in Hong Kong

    Cathay Pacific The Wing Lounge in Hong Kong

    Previously, we lived close to a United Airlines hub, so we initially chose Star Alliance and accumulated quite a few points (or I should say my husband did due to his business travel).

    Star Alliance is one of the biggest airline alliances and has an incredibly robust network of flight options. You can basically travel anywhere using this alliance.

    Now, we live close to an American Airlines hub, so we have switched to Oneworld. We love traveling to Asia.

    Cathay Pacific has many routes to Asia and is one of American’s alliance partners. Because of my husband’s status with American, Cathay Pacific recognizes his status which allows access to their top lounges when we travel through Asia.

    The Pier First Class Lounge in Hong Kong is probably my favorite lounge ever! Think free wagyu beef cheeseburgers, 15-minute massages, and a private shower after a long flight. Oh, yeah.

    The downside to Oneworld is there are not nearly as many travel options as Star Alliance.

    02- Pick a Travel Credit Card

    Chase vs Amex Travel Credit Card


    If you only can pick one, go with the Chase Sapphire Reserve hands down for two reasons.

    The first reason is the $200 airline fee credit with Amex is very difficult to use because it only applies to incidental fees, checked bags, and in-flight refreshments on the one airline you select for the entire year.

    You used to get around this by purchasing gift cards from the selected airline and using them to pay for flights, but they closed this loophole. 

    The second reason is there are many places internationally that do not accept Amex.

    The big perks of using Amex are access to their Centurion lounges, their concierge service, and the Amex offers they send out for select retailers.

    On the other hand, getting value out of the Chase Sapphire Reserve card is incredibly easy. The annual fee for Chase Sapphire Reserve is $550.

    If you travel at all, you are going to be able to easily use the $300 annual travel credit. This drops it down to $250.

    If you already enjoy DoorDash services every year, take another $60 off. Now, you are down to $190.

    If you decide to take advantage of the Global Entry credit (which you should! if you love international travel), subtract another $100. You are left with $90.

    Now you must decide if you will get more than $90 worth of Priority Pass access, car rental insurance, DoorDash delivery fees, and Lyft perks.

    We use the Priority Pass lounges frequently, so for us, that alone adds up to way more than $90 a year. If you cannot tell, I love this travel credit card!

    Plus, you can redeem your points through the Chase Travel Portal at 1.5x the rate, which will be explained later in this guide.

    PRO TIP: Another consideration in the Chase vs. Amex battle is to consider your airline alliance. Chase and Amex have specific airlines they work with as transfer partners. Check to see which credit card partners with your airline alliance. That may help you decide which credit card is best for you.




    Courtesy of Shutterstock: Travel hacking 101- pick a card with a big bonus offer

    I would only sign up with a travel credit card WHEN there’s a nice welcome bonus offer.

    For example, the Chase Sapphire Reserve is offering an 80,000 bonus point offer when you sign up and spend $4,000 within the first three months of the open account. At one point, Chase was offering a 100,000 bonus points offer. However, no one has seen that offer floating around for years.

    Also, it’s important to know Chase has the 5/24 rule. You will be denied all Chase cards if you’ve opened 5 new credit cards in the last 24 months.

    The standard welcome offer for American Express Platinum right now is 100,000 points, BUT you may be matched for even a higher offer of 125,000 or even 150,000 points!

    You must spend $8,000 in the first 6 months to receive the points. If you are worried about hitting that minimum spend to get the bonus, time it around a big purchase (like a home renovation project or a new computer).

    An easy way to see if you are matched for the lucrative Amex offer is to go to and input your demographic information. It will not affect your credit score. It’s only a soft pull.

    I’ll be honest. The American Express Platinum is not my favorite travel credit especially because not everyone accepts it when you travel internationally. I use it mainly for the Centurion Lounges, the Uber credits, and the occasional Amex offers.

    The reason I signed up for it was because I was offered the high bonus offer. The 150K offer is insane. It’s worth roughly around $3,000! Here’s a snapshot of all the amazing free travel you can book with 150K Amex points.

    PRO TIP:  If you find that you are not getting value out of the travel credit card after a year, you have two options when it gets close to your card renewal date. Call customer service and let them know you are considering canceling. Oftentimes, they will offer a retention offer in the amount of credit or points to keep you. If there’s no retention offer, another option is to downgrade the card to one with no annual fee.



    Do NOT add your spouse or partner to your travel credit card as an authorized user.

    It’s best to have your spouse/partner open up their own card, so they can also hit the bonus offer.

    This assumes that you are able to spend the minimum required for the welcome offer AND you are still paying off your credit card balance in full every month.

    03- Maximize Points with the Chase Trifecta

    Never pay cash for travel

    Never pay cash for travel

    Never pay cash or use a debit card for purchases.

    Use your travel credit card for EVERY purchase.

    It all adds up. You always want to earn points. Yes, I am guilty of even charging $1 for a gas station donut. Never lose out on points.  

    Chase Trifecta Travel Credit Cards

    Travel hacking 101: Use the Chase Trifecta Travel Credit Cards



    I use this credit card for all travel-related expenses (flights, hotels, rentals, Uber/Lyft, parking, etc) and dining purchases to get 3x points. $550 annual fee.



    This card has rotating 5x quarterly bonuses. For example, one quarter Chase may give you 5x points on all grocery and gas purchases. Then all of my grocery and gas purchases for those 3 months go on this card. I only put the 5x categories on this card. $0 annual fee.



    This card will give you 1.5x points on all purchases. If my purchase does not fall in the travel or featured 5x quarterly bonus category, then the purchase goes on this credit card. $0 annual fee.

    You can see how easily the points add up.

    When I redeem those points, I transfer all the points from Chase Freedom and Chase Freedom Unlimited to my Chase Sapphire Reserve credit card.

    Then I redeem those points through the Chase travel portal for hotels (or flights if you choose) at 1.5x the rate.

    Say you have 200,000 Chase Ultimate Rewards points, which is equal to $2,000 USD. If you redeem those same 200,000 points through the travel portal, they are now worth $3,000 USD. Incredible value!

    04- Double Dip

    1 transaction. 2 types of points.

    This is my favorite way to accumulate more points and miles. There are four easy ways to double dip when you are first starting out: shopping portals, dining programs, Rakuten, and Amex/Chase offers. 



    We are all shopping online now from groceries to clothing to home goods. I don’t know about you, but I rarely go to actual stores now.

    In addition to the points you receive on your credit card, what if I told you if you take one extra step you can collect even more points to go towards that free vacation?

    Welcome to shopping portals!

    These portals offer hundreds of different merchants that you are likely already buying from. Think Apple, Home Depot, Sephora, etc.

    Many airlines (American Airlines and United) and banks (Chase) offer shopping portals. You must log in to the portal’s website, select the merchant you want, and click the link through the portal to direct you to the merchant’s website.

    Once you complete the purchase, it will take a few days or weeks to see the points in your account.

    How do you know what shopping portal to use? Go to Cashback Monitor. Type in your merchant, and see which portal is offering the most amount of points or cash back.

    Cashback monitor screenshot

    Cashback Monitor screenshot

    For example, say you need to purchase a cute sundress from Macy’s for that wine vacation you are planning to Portugal this summer.

    Type Macy’s into Cashback Monitor’s search box. You find American Airlines Advantage is offering up to 4 miles/$ spent. See the screenshot above.

    Log into your American Airlines account and select Macy’s in the shopping portal. American Airlines will take you directly to Macy’s website.

    Complete the purchase with your Chase Freedom Unlimited card and receive 4 miles/$ PLUS the 1.5x Chase points! Cha-ching.



    Carpaccio of Herb-Crusted Elysian Fields Baby Lamb Loin with Caesar Salad Ice Cream at The Inn at Little Washington Restaurant

    Dining out

    Love dining out or grabbing takeout when you don’t feel like cooking?

    Here’s yet another opportunity to double dip.

    Certain airlines (American, Alaska, Delta, Spirit, JetBlue, Southwest, United) and hotels (Hilton, IHG, Marriott) offer dining rewards programs, which are operated by the Rewards Network.

    Most points experts agree airline miles are more lucrative than hotel points.

    All you need to do to get started is sign up for the program, register your travel credit card, and pay for your meal at a participating restaurant. Check which restaurants participate by typing in your zip code on the program’s website.

    For example, if you join the AAdvantage Dining Program, you’ll get 1 mile per dollar paid, 3 miles per dollar if you agree to receive emails from the program, or 5 miles per dollar if you receive emails AND make 11 transactions in the calendar year.

    Now you’ll get extra miles per dollar spent PLUS 3x the points with your Chase Sapphire Reserve card for a lovely meal out.


    #3- RAKUTEN

    Rakuten membership

    My Rakuten membership

    I have been a member of Rakuten since 2010! It used to be known as Ebates. It’s a rewards program, where you can get cash back or extra Amex points for purchases you were going to make anyway.

    To date, I have earned a total of $3,696.76!

    Not bad considering there is little extra effort involved.

    Go to Rakuten’s website and type the merchant you are looking for in the search box. The merchant will pop up if it’s a participating retailer with Rakuten.

    For example, we recently booked a hotel through I first went to Rakuten and typed in the search box. The current offer is 4% cash back.

    I clicked on the “shop now” link, which directed me to the website. Once I complete my stay at the hotel in the next coming months, I will receive a check for 4% cash back.

    Not bad for taking that one extra step. 

    PRO TIP #1Always check for mobile-only pricing on travel booking websites. When I recently went to through Rakuten’s website on my cell phone, I was shocked to see the cost of my hotel was $447 cheaper for a 4-night stay in the Maldives!! Not only am I getting 4% cash back with Rakuten but an additional $447 simply because I made the reservation on my phone instead of my desktop.

    PRO TIP #2: Reach the required amount of stays with and become a Genius member for even deeper discounts (10-20%)!

    Mobile only price on

    Screenshot of mobile-only pricing on



    Amex offers screenshot

    Travel hacking 101: Take advantage of Amex offers

    Amex Offers are another great way to double dip. Amex will periodically offer you additional discounts at select retailers. The offers will be listed on your Amex’s home page after you log in.

    The Amex Offers will list what you need to spend to get the offer and the expiration date. You have to select “Add to Card” next to the offer to get the discount when you use your Amex card.

    Remember these offers are in ADDITION to the points you will already be receiving on your Amex card for the purchase. 

    Chase has started a similar program, but I haven’t found the offers to match as well to my personal shopping habits.  

    05- Know the Partnerships 

    There are certain partnerships you need to remember to keep banking more points. Here are examples of a few of them.



    Link your Uber and Marriott Bonvoy accounts and get 3x hotel points per dollar spent on Uber rides and 2x hotel points per dollar spent on Uber Eats.



    Link your Lyft and Delta SkyMiles accounts and get 1 mile per dollar spent on Lyft rides. If you use your Chase Sapphire Reserve card to pay for the ride, you can double dip and get 10x the total points!



    Link your American Airlines and World of Hyatt accounts. Earn 1 Hyatt point per dollar spent on American Airlines flights. Earn 1 American Airline mile per dollar spent on Hyatt stays.



    Sign up for a British Airways account. Book your Airbnb stay or Airbnb experience through this British Airways’ link. Then collect 3 Avios miles per £1/€1/$1 spent with Airbnb. These miles can be used later for reward flights.

    06- Lookout for Mistake Fares


    Courtesy of Shutterstock: Travel hacking 101- look for mistake fares

    I haven’t taken advantage of a mistake fare yet but can’t wait until I do!

    A mistake fare occurs when there’s an airline price glitch resulting in a massively cheap flight. This mistake can be due to technology issues, human error, or communication problems.

    Think like a $63 roundtrip flight to Chile from The United States. 

    Now, you could just get lucky and happen to come across one, or you can constantly search specific routes. Who has the time for that?

    A better way to stay informed if a mistake fare does occur is to join a subscription like Scott’s Cheap Flights. Add your home airport, and their expert team will continuously scour the internet to find you the best flight deals.

    If you do find a mistake fare, act quickly because normally it only lasts a few hours before the error is corrected.  

    Remember the 24-hour rule. Any flight that touches United States soil allows you to cancel your flight for free within 24 hours of booking as long as it’s not too soon before the day of the flight.

    Book the mistake fare, figure out the details, and cancel for free in 24 hours if it’s not going to work. 

    07- Always Check the Redemption Value

    We love getting good value for the money.

    I am always looking for a good coupon or promotion before I make a purchase or going back to get a price adjustment on something I just purchased if the price drops. 

    Once you have accumulated all those airline miles or hotel points, you will want to start cashing them in for free flights or hotels. You will need to know if you are getting a good redemption rate for all those hard-earned miles and points.

    There are two ways to figure this out. One requires a little math, and the other is plug and chug.



    Redemption Value Formula for Airline Miles or Hotel Points

    Travel hacking 101: Redemption Value formula

    Plug in the information using the formula above. Then go over to the Points Guy’s estimated Monthly Valuations of some of the top hotel brands and airlines.

    • If my redemption value is < the estimated Monthly Valuation of that particular airline/hotel, then BOOK WITH POINTS/MILES.


    • If my redemption value is < the estimated Monthly Valuation, then PAY CASH. It’s not worth the points.


    • If it’s equal, then it’s your call but some factors may lean you in one direction than the other. For example, some locations add an occupancy tax to the hotel rate. But if you pay with points, you may avoid that dreaded tax.


    Alternatively, use the Points Guy’s Calculator to quickly determine if you are getting good value if you redeem those airline miles or points.

    08- Airlines Miles are More Valuable 

    Airplane flying in the air

    Courtesy of Shutterstock

    You put all these tips into practice, and now you have accumulated a bunch of points on your travel credit card.

    Now what? How do you start redeeming this travel currency into free flights and hotels?

    Chase and Amex allow you to transfer your points to airline partners and hotel chains.

    Chase has 11 airline partners and 3 hotel chains, and Amex has 17 airline partners and 3 hotel chains. When you are ready to redeem your points, transfer your Chase Ultimate Reward (UR) points or your Amex Membership Reward (MR) points to your selected airline or hotel.

    Occasionally, Chase and Amex will offer a bonus for point transfer. For example, Chase Sapphire Reserve is currently offering 30% more bonus points if you transfer your credit card points to Virgin Atlantic Flying Club.

    Once the points are transferred, complete the booking. Always check your redemption value to make sure you are getting good value out of your points.

    In general, airline miles are more valuable than hotel points. The redemption values can be pretty incredible. Of course, this all depends on your personal travel needs and goals.

    We used airline miles on our Africa trip to get us from the United States to Zimbabwe and from Johannesburg back to the United States. This saved us an incredible $3,296 on flights between the two of us!

    Don’t miss my article on how we used airline miles and Chase points to save over $6,800 on our dream Africa trip!

    09- Redeem at Chase Travel Portal

    The other way you can redeem points is through the Chase travel portal.

    If you have the Chase Sapphire Reserve Card, your points get boosted from 1 cent per point to 1.5 cents per point.

    For simple math, let’s say you have 200,000 Chase points sitting in your account. Those points are worth $2,000. However, if you go through the Chase travel portal to book that cute little boutique hotel in Aruba, the value gets boosted 1.5x to 300,000 points. A $3,000 value!

    Here is an example of how we put our Chase points into practice.

    We enjoyed an epic 2-week trip to Africa that would have cost a small fortune. However, our Chase UR points erased most of our hotel costs. We used 239,138 points to save us a whopping $3,587.07 on hotels! Here’s proof below.

    Airline and Credit Card Points Used for Africa Trip

    Airline and Credit Card Points Used for Africa Trip

    Final Thoughts

    I hope this travel hacking 101 guide gets you well on your way to the world of accumulating miles and points toward free travel! 

    Pick your airline alliance, get the Chase Trifecta with a big bonus offer, start double dipping, and cash in those points if you’ve got a good redemption value.

    You will be earning that free vacation before you know it!

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    Questions about my travel hacking 101 tips?

    Let me know in the comments below!


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