How To Use Business Expenses to Travel Free: Booking Awards

by David

Most business owners and even many self proprietors accrue expenses far exceeding what the average consumer spends in a given month. As a business owner, if you’ve already selected the right credit cards for your unique expense profile, the next step is to cash in those points and miles for free flights and hotels once equipped with a value maximizing redemption strategy.

About 98% of all American businesses (over 24,000,000!) have fewer than 20 workers according to the Small Business and Entrepreneurship Council. For those business owners able to navigate not only the points and miles earning labyrinth but also the award booking process, outsized rewards are there for the taking.

American Airlines Business Class onboard the B777-300ER. Source: American Airlines

Leverage your business expenses correctly and you can earn a lot of comped flights in this cabin. Image by American Airlines

This section in our four part series covers the next step in the process of converting business spend to travel rewards.

  1. Earning Business Travel Rewards
  2. Maximizing Business Spend
  3. Navigating the Award Booking Process for Businesses
  4. Leveraging Business Perks and Upgrades

Just as strategies to maximize spend depend upon the specifics of your business (covered in section two), the optimal award redemption strategy depends upon specifics of travel, including duration of flights, class of service and geography.

Using Chase Ultimate Rewards

There are two main ways to use most credit card points. The points can be transferred to various rewards programs, including airline frequent flyer mile programs and hotel rewards programs, or they can be redeemed for cash value through a “portal”.

Using the Chase Ultimate Rewards Travel Portal

Redeeming flights and hotels through the Chase Ultimate Rewards travel portal can be a sound approach for booking business travel awards, and is certainly easy, but doesn’t typically provide the maximum point value.

Unlike airline loyalty programs where travelers are subject to award availability, close-in booking fees, complex routing rules and limited inventory from that airline only and its partners, Chase’s travel portal operates similarly to online travel agencies in that any flight can be booked with cash, but also as an award at a fixed rate based on the fare price.

Also contrary to booking awards directly with airlines, travelers booked on awards through the Chase travel portal generally earn both normal reward miles and elite qualifying miles for their flights, which is a valuable, and sometimes expected, perk for small business employees asked to travel on behalf of a company.

a close up of a credit card

The Chase Ink Business Preferred Credit Card provides a 1.25 cents per point redemption rate when paying for travel with points through the Chase Ultimate Rewards travel portal on any hotel, car rental or flight, and so a $400 flight would require 32,000 Chase Ultimate Rewards points to ticket the fare. If the traveler also has, however, the personal Chase Sapphire Reserve card, then Ultimate Rewards points from the business card can be transferred to the personal card to leverage the Chase best 1.5 cents per point redemption rate, where a $400 fare would require only 26,667 Ultimate Rewards points.

Click here for information on this card and others like it.

Transferring Points to Airlines: Options for Domestic Travel

In addition to redeeming Ultimate Rewards points directly through the Chase travel portal, business travelers also have the option to transfer their points into nine airlines for award bookings:

  • Aer Lingus AerClub
  • Air France Flying Blue
  • British Airways Executive Club
  • Iberia Plus
  • Korean Air SkyPass
  • Singapore KrisFlyer
  • Southwest Rapid Rewards
  • United Mileage Plus
  • Virgin Atlantic Flying Club

Critically, before transferring points verify that there is award seat availability on dates and times that fit within your travel schedule. Some availability can be checked through frequent flyer program websites, while others require a phone call.

Alternately, for complex bookings, consider using an award search service like Juicy Miles or Points Pros, which will take care of ensuring availability and maximizing point redemptions.

British Airways Executive Club – Best for Domestic Economy Class American and Alaska

Because British Airways Executive Club award chart is distance based, short-haul domestic flights under 1,150 miles on partners like American Airlines and Alaska Airlines can be booked for 7,500 British Airways Avios in economy class. If American has saver award availability for a nonstop flight from Chicago O’Hare (ORD) to Atlanta Hartsfield (ATL), the flight would cost 7,500 Ultimate Rewards Points, transferred instantly to Avios.

To compare, 7,500 points redeemed through the portal would cover airfare worth $95. When flights can be two or even three times more expensive, transferring to British Airways to book is a much better option.

Singapore Airlines – Domestic Flights and First Class Flights on United Airlines

Ultimate Rewards transfer partner Singapore Airlines KrisFlyer enables business travelers to redeem fewer points to fly on its domestic partner, United Airlines.

A standard domestic one-way first class saver award on United Airlines would cost 25,000 points if booked through United MileagePlus (also a Chase transfer partner). The same seat costs 20,000 points when booked through Singapore KrisFlyer miles.

When compared to a 1.25 cents per point redemption rate through the Chase travel portal, domestic first class flights that would other cost over $250 should be booked through Singapore KrisFlyer.

United Airlines' Boeing 747. Source: United Airlines

United Airlines’ Boeing 747. Image by United Airlines

United Airlines itself is an Ultimate Rewards transfer partner, which United business travelers may leverage for 12,500 mile  economy class saver awards. Southwest Airlines is yet another Ultimate Rewards transfer option, and its flights can be redeemed at a typical rate of 1.5 cents per point based on the price of Southwest airfare.

Transferring to Chase Hotel Partners

Although hotels can be booked at 1.25 cents per point through the Chase Ultimate Rewards travel portal, certain hotels may cost fewer points through transferring points directly into hotel loyalty programs:

  • World of Hyatt
  • IHG Rewards Club
  • Marriott Rewards
  • Ritz Carlton Rewards

For instance, the highest tier (category 7) Park Hyatt New York often costs around $800 before taxes. If booked through the Chase Portal, this would run around 53,000 Chase Ultimate Rewards points per night.

Park Hyatt New York is within reach with the World of Hyatt Credit Card signup bonus

Even top-tier Park Hyatts, like the famous one in New York City, are within the intro bonus offered on the new World of Hyatt Credit Card.

That top-tier Hyatt costs only 30,000 points when booked through the World of Hyatt program, which accepts Chase Ultimate Rewards points at a 1:1 ratio.

World of Hyatt lowest tier (category one) properties, redeemable for 5,000 points, as well as mid tier (category four) properties, redeemable for 15,000 points, tend to provide better value relative to the cash rate more often than properties in  other category levels.

If hotel free night awards are available for desired dates through the brand’s loyalty program, transferring points directly often provides the best value even though points are not earned for the stay. Unlike flight awards, hotel award stays do generally count toward elite status qualification.

In addition to World of Hyatt, Chase Ultimate Rewards can also be transferred  to IHG Rewards Club and Marriott Rewards at a 1:1 ratio.

Best Chase Transfer Options for International Travel

Business travelers looking to book international transoceanic award flights should also perform a cost analysis between partner airline loyalty programs award redemption rates and flights available through the travel portal. Potential fuel surcharge or international tax add-ons make this comparison slightly more complex.

United Airlines Economy Class Dreamliner 787

United economy class on the Boeing 787 Dreamliner. Image by United Airlines.

A round-trip economy class flight on Chase Ultimate Rewards partner United Airlines between Newark Liberty (EWR) and London Heathrow (LHR) over two dates in September costs $1,000 in cash, or 60,000 United MileagePlus miles plus $185 in taxes and fees.

In this scenario, booking two 30,000 mile segments between North America and Europe directly with United – even when considering miles otherwise earned for the flight – offers better value relative to booking the award through the Chase travel portal at 1.25 cents per point.

a green and white airplane in the sky

Ultimate Rewards partner Aer Lingus AerClub offers a sweet spot redemption for off-peak travel between US destinations ORD, EWR, Boston Logan (BOS), Washington Dulles (IAD), New York (JFK) or Hartford Bradley (BDL) and either Dublin Airport (DUB) or Shannon Airport (SNN) for 13,000 Avios plus taxes and fees one-way (26,000 Avios round-trip) in economy class.

Since BA does not show Aer Lingus availability in its award search engine, I find it easier to login to through my Aer Lingus membership to view and book awards online. If you have a trove of the British Airways variety of Avios, however, it’s also possible to call BA and use those instead.

Best Value: Booking International Business and First Class

International Business and First Class flights often cost upwards of five times more than economy fares on the same flight. Even at a generous 1.5 cents per point redemption rate, a $5,000 one-way flight would cost an exorbitant amount of points through the Chase portal.

a close-up of a plane

Iberia’s Airbus A330 Business Class

Chase Ultimate Rewards transfer partner Iberia Plus has a sales promo offering off-peak round-trip award in business class for 51,000 Avios and about $220 between ORD and Madrid Barajas (MAD) in February. Those same flights would cost over 300,000 Ultimate Rewards points through the Chase travel portal.

Korean Air SkyPass also offers premium cabin sweet spot redemptions. Awards between North America and Asia cost 62,500 miles in business class or 80,000 one-way. Flights between North America and Europe on partners like Delta, Air France and KLM cost 80,000 miles round-trip in business class or 100,000 miles round-trip in first class (Korean partner awards can only be booked round-trip).

International World of Hyatt redemptions, as with domestic awards, generally provide the best value for transferring Chase Ultimate Rewards to hotel loyalty programs. When a desired redemption value cannot be reached or the destination is in a location where Hyatt lacks a strong footprint, business travelers should also look to Marriott Rewards.

a few people standing at a reception desk

The Crowne Plaza Panama Airport is currently available for 10,000 points via IHG Rewards Club PointBreaks. Image by Crowne Plaza Panama Airport

IHG Rewards Club has a fantastic PointBreaks program, whereby a select few hotels each quarter can be booked with either 5,000, 10,000 or 15,000 IHG Rewards points, significantly less than the normal cost of included properties. Business travelers should always check here to discover whether any PointBreaks properties line up with their international (and U.S.) destinations and dates of travel.

Using American Express Membership Rewards

Like Chase, American Express Membership Rewards Points can be redeemed through a travel portal and applied toward cash fares, or can be transferred to a number of partners:

  • Aeromexico Club Premier
  • Air Canada Aeroplan
  • Air France Flying Blue
  • Alitalia MilleMiglia
  • All Nippon Airways Mileage Club
  • Asia Miles (Cathay Pacific)
  • British Airways Executive Club
  • Delta Air Lines SkyMiles
  • El Al Matmid Frequent Flyer Club
  • Emirates Skywards
  • Etihad Airways Guest
  • Hawaiian Airlines Hawaiian Miles
  • Iberia Plus
  • JetBlue TrueBlue
  • Singapore KrisFlyer
  • Virgin Atlantic Flying Club
  • Choice Privileges Rewards
  • Hilton Honors
  • Starwood Preferred Guest

American Express Travel

For business travelers earning American Express Membership Rewards points through credit card spend, the American Express Travel portal may offer the highest redemption value.

The fixed redemption rate is not uniform amongst all Amex Membership Rewards earning cards, but rather varies depending on the card used to login to Amex Travel.

American Express Platinum Card

The Business Platinum Card from American Express Open nets 1.54 cents per point when paying for airfare through Amex Travel on a selected airline of choice in any cabin or on any airline if flying business class or first class.

Technically this elevated rate operates as a 35% rebate on fares booked at a standard one cent per point, and so given a $400 fare, the traveler would need 40,000 Amex Membership Rewards points at their disposal to ticket the award before receiving about 14,000 Amex Membership Rewards points back (up to 500,000 points back per calendar year).

JetBlue Mint Fare Deal $399 BOS Boston

American Express points can be transferred directly to JetBlue, which offers a bonus when applying points to Mint business class seats.

JetBlue Mint remains at the top of the heap for domestic first class, and with one-way fares dropping to as low as $399, or about 26,000 AMEX Membership Rewards points after a 35% rebate, transcontinental business travelers intersecting with JetBlue’s Mint route network can fly in premium comfort.

Amex Travel does allow card holders to select Southwest as their airline of choice and earn the rebate through an end around method when using the Business Platinum Card from American Express Open to book the flight via Southwest.

Hotels and economy class flights (other than on the airline of choice) can only be redeemed at one cent per point, and so alternative redemption strategies are likely to provide greater value for categories of travel failing to qualify for the rebate.

Best Transfer Options for Domestic Travel

In addition to redeeming points with AMEX Travel, business travelers with a gaggle of Amex Membership Rewards points have the option to transfer their points into 16 different airline loyalty programs and 3 hotel loyalty programs.

Business travelers can take advantage of the same benefits from British Airways Executive Club’s distance based award chart mentioned above through AMEX Membership Rewards as well, though at a less favorable 250 Membership Rewards points to 200 British Airways Avios ratio.

Air Canada Aeroplan, a United Airlines alliance partner, allows travelers to redeem the same amount of Aeroplan miles as United MileagePlus miles for domestic economy class on United (i.e. 12,500 miles), and should specifically be considered for last-minute bookings on United flights given that Aeroplan does not assign close-in fees.

American Airlines transcontinental business class A321

American Airlines A321T Business Class. Image by American Airlines.

Etihad Guest, an American Airlines alliance partner, has a particular sweet spot redemption opportunity for domestic travelers flying between JFK and either Los Angeles (LAX) or San Francisco (SFO) who are hoping to experience American’s Airbus A321 Transcontinental planes, which have both First Class and Business Class cabins.

To find eligible seats, you’ll need to search for “SAAver Awards” on American Airlines’ website before transferring points and calling Etihad to book. (Again, for those in a crunch, Juicy Miles or Points Pros will take care of the technicalities.)

Transcontinental AA flights cost 25,000 Etihad Guest miles in business class, one-way. The A321 business class cabin is equipped with lie-flat seats and business passengers have access to AA Flagship Lounges at LAX and JFK. American charges 32,500 AAdvantage miles for its business class and 50,000 miles for its First Class, which offers private seating and access to Flagship First Dining in its Flagship First lounges.

Business travelers may also leverage AMEX Membership Rewards transfer partners to fly domestically with Delta Air Lines. Business travelers may choose to transfer Membership Rewards points directly to Delta’s SkyMiles program. However, with Delta moving away from a defined award chart, travelers may also find it more reliable to redeem flights on Delta through Virgin Atlantic Flying Club or Air France Flying Blue, which prices Delta one-way segments at 12,500 miles – even at times when Delta is not showing low-level availability.

For business travelers seeking to maximize value for hotel stays, AMEX Membership Rewards points can be transferred into Marriott Rewards and Hilton Honors, though at unfavorable transfer ratios, as well as Choice Privileges Rewards.

Although hotels in the Choice Privileges Rewards program are generally thought of as budget properties which tend not to have high redemption value within the United States, Choice points can also be used to redeem free nights at Preferred Hotels & Resorts properties, a group of luxury boutique hotels with a global footprint.

a pool and palm trees by a resort

The Montage Laguna Beach, a Preferred Hotels & Resorts property, can be booked with Choice Privileges Rewards points plus cash for free night awards. Image by Montage Laguna Beach

Choice Privileges Rewards redemptions for Preferred Hotels & Resorts properties are structured into four tiers with corresponding points plus cash award bookings:

  • 25,000 points or 10,000 points and $112.50 per night
  • 35,000 points or 10,000 points and $187.50 per night
  • 45,000 points or 10,000 points and $262.50 per night
  • 55,000 points or 10,000 points and $337.50 per night

Within the US, a number of Preferred Hotels & Resorts properties offer business travelers superb value, particularly for points and cash redemptions. For instance, the Montage Laguna Beach, which is rarely available for less than $800 per night all in, has generous award availability for nightly redemptions at 55,000 points or 10,000 points and $337.50.

Other Preferred Hotels & Resorts properties that maintain ample award availability and can provide outsized value from points and cash award bookings include the Scarlet Huntington Hotel in San Francisco (10,000 points and $262.50 per night), the trendy, yet historic, Ambassador Chicago hotel (10,000 points and $187.50 per night) and the Boston Harbor Hotel (10,000 points and $337.50 per night).

Best Amex Transfer Options for International Travel

Amex Membership Rewards’ airline transfer partners facilitate a wealth of opportunities to redeem flight awards for international travel.

Business travelers can transfer AMEX Membership Rewards points to Iberia Plus for the same Midwest and East Coast to Europe business class sweet spot awards as is available with Chase Ultimate Rewards transfers, though at a less favorable 250 Membership Rewards points to 200 Iberia Avios ratio.

Singapore KrisFlyer, transfer partner of both banks, also provides a number of advantageous international redemption options. Economy class awards between the U.S. and Europe cost only 27,500 Singapore KrisFlyer miles (rather than the common 30,000 miles for low-level availability across most airlines) on partner flights within the Star Alliance airline partnership, which includes European members Lufthansa, Swiss Airlines, Austrian Airlines, Brussels Airlines, SAS and LOT Polish Airlines.

The new Suites Class can be converted into a double bedroom. Source: Singapore Airlines

The new Suites Class can be converted into a double bedroom. Image by Singapore Airlines

Additionally, business travelers seeking a unique luxury experience flying Singapore Airlines’ Airbus A380 operated flights equipped with its new suites can redeem first class awards for 76,000 miles on Singapore’s fifth freedom JFK to Frankfurt Airport (FRA) route, though finding open suites can be a challenge with miles.

Etihad Guest miles can be redeemed for valuable American Airlines partner awards internationally as well as domestically. 50,000 miles gets you a one-way business class award on American between the US and Brazil, Argentina, Paraguay, Uruguay, Chile or Bolivia.

JFK to Brussels (BRU) each way for 44,000 miles in business class on Brussels Airlines is another partner sweet spot available for redemption within Etihad Guest.

For business travel to Japan, AMEX Membership Rewards partner All Nippon Airways ANA Mileage Club offers very cheap off peak awards between North America and Japan over the months of January, February and April for 40,000 miles roundtrip in economy class and 75,000 miles roundtrip in business class.

a plane flying in the sky

Delta’s A350 can be booked by transferring Amex points to Delta, or sometimes more affordably by transferring the points to Air France Flying Blue or Korean SkyPass. Image by Delta Air Lines.

Although Amex Membership Rewards partner Delta no longer publishes an award chart, savvy business travelers should also consider the airline’s loyalty program for flights to Europe, Australia and Asia given that Delta does not impose additional fares for these itineraries on either its own flights or its partners’ flights. Delta does, however, impose additional fares on flights originating in Europe, and so travelers to Europe should use their Delta SkyMiles to either book round-trip awards or find a non-Delta alternative for the return flight.

With this many options to consider along with the complexities, availability limitations and fee structures of each individual airline program, it is often most convenient to rely on award booking experts, such as those at Juicy Miles, to help navigate the award booking process for international premium cabin flights.

While Choice Privileges Rewards hotel redemptions for its own brands tend not to provide great value in the United States, in relatively expensive overseas markets such as the UK, Scandinavia and Japan, where other hotel programs may not be as well represented, business travelers should not overlook Choice Privileges Rewards as an option to redeem free hotel nights.

a patio with chairs and a table

Image by At Six, An Ascend Hotel Collection Member, Stockholm

An award search in Stockholm over a random night in August provides over 10 properties showing availability between 10,000 and 20,000 points, with some redemption values exceeding three points per dollar when compared to the full nightly rate.

In addition to Hilton Honors hotels, Marriott Rewards properties may also be redeemed through AMEX Membership Rewards points transfers, and given the hotel program’s 30 brands, Marriott’s worldwide footprint provides business travelers with potential free night awards on all four corners of the globe if, and when, higher value options are unavailable.

Using American AAdvantage Miles

Unlike competitors Delta, United, Southwest and JetBlue, American Airlines is neither a transfer partner of AMEX Membership Rewards nor Chase Ultimate Rewards. Although American partner airlines, such as Etihad Airways, allow its members to book awards on American flights through points transfers from either bank program, American’s award chart has standalone value for travelers with considerable American AAdvantage balances.

an airplane on the runway

American Airlines Boeing 787 Dreamliner. Image by American Airlines

In economy class to and from Europe, for instance, American offers off-peak awards for over one quarter of the year from January 10th through March 14th as well as from November 1st through December 14th for 22,500 miles each way, a significant 7,500 mile savings, or 25% off, compared to the typical rate.

Economy class business travelers can further take advantage of American’s off-peak award pricing to Colombia, Ecuador, Peru, Bolivia, and Manaus (Brazil) for over two-thirds of the year for 17,500 miles each way rather than the typical 20,000 mile rate. Business class flyers can fly year round to those same South American destinations for only 30,000 miles at the “SAAver Award” level on both its own flights as well as partner LATAM Airlines.

American has slightly more favorable business class rates to Japan and Korea than Korean Air does, at 60,000 miles each way, and offers the same attractive rate in first class as Korean does for a total of 80,000 miles each way.

Far flung destinations Australia and New Zealand are also in reach on American routes from LAX as well as partner airline routes on Qantas from Dallas/Fort Worth (DFW), San Francisco International Airport (SFO) and LAX for a total of 80,000 miles each way in business class.

a room with brown leather couches and pillows

The Etihad Apartment is the most spacious first class cabin bookable with American AAdvantage Miles.

Although Etihad miles are better off redeemed for flights on American for particular routes, the opposite also holds true for certain Etihad segments. To fly Etihad’s premier first class Apartments on routes where it operates an Airbus A380, less American miles are typically required than if business travelers were to book direct with Etihad. For instance, Etihad’s JFK to Abu Dhabi (AUH) route requires 115,000 American miles to fly in one of the most sought after first class suites in the sky as opposed to over 135,000 Etihad miles.

Other Fixed Rate Redemption Bank Currencies, Bank of America and Capital One

Fixed rate programs, like those offered by Bank of America and Capital One, are not nearly as valuable as the rewards programs operated by the likes of Amex, Chase and Citi, but they are much simpler to use.

Bank of America’s travel rewards points can be redeemed at one cent-per-point for any purchases made through the Bank of America Travel Center. They can also be converted to statement credits on any purchases coded as “travel expenses,” including typical purchases such as airfare and hotels and more obscure categories including timeshares, campgrounds, amusement parks, aquariums and zoos.

Business travelers can redeem Capital One Spark Miles at a one cent per point rate on any flights, hotels, cars and activities purchases made at Capital One Rewards as well as for statement credits using the “Purchase Eraser” on eligible travel purchases including airfare, hotels, rail, car rentals, limos, bus lines, cruise lines, taxis, travel agents and time shares within 90 days of the date of purchase.

The Upshot

The redemption versatility of both Chase Ultimate Rewards points and AMEX Membership Rewards points elevates these bank programs as principal options for business travelers to focus in on. The flexibility to redeem awards either directly within bank travel portals or through transferring points to hotel and airline loyalty programs enables businesses to maximize the value of hard-earned points and miles.

Whether seeking business class comforts or simply trying to get from point A to point B, business travelers can navigate various award redemption strategies to select the one most suitable for them based upon their travel itineraries and premium preferences.


The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

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Vet&Banker July 20, 2018 - 2:00 pm

This is decent content, but there’s nothing I see in this series that’s different for business owners than for regular consumers except level of spend (and writing off expenses, I guess). It’s good to draw attention to the rewards small business owners should be getting, but how about information that focuses on *business* rewards, like business travel programs? For instance, AA’s Business Extra program points that “double stack” with AA miles, providing upgrades and free trips? Or United’s Perks Plus, which has options for drink packages, United Club membership, or flights? Maybe teach us something Choice ‘s Business Travel program.

I am not saying this isn’t good info. Just that this is standard fare for all, instead of extra info for business owners.

David July 23, 2018 - 2:42 pm

I appreciate the feedback. Stay tuned for additional content!

Leo July 20, 2018 - 3:13 pm

What a fantastic article. Very well written. I bookmarked it for my future uses coming up with american + Amex miles & points. Thank you so much

David July 23, 2018 - 2:44 pm

Thanks for the kind words Leo, I’m glad you found the post useful.

Bus rental in Dubai February 17, 2022 - 9:52 pm

Keep it up DAVID,


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