How much did it cost to fly to Cape Cod that one time? Oh yeah, nothing.

The question is always packaged a bit differently depending on who asks, but suffice it to say that I'm often asked some variation of the same question question: I am miserable when I travel because [it's so expensive, it's so uncomfortable, it's so inconvenient], so what are the core credit cards I should sign up for to make it all a bit better?

I actually thought quite a bit about how to write this, because I think that folks who really know this material often make the mistake describing it as a litany of benefits that seem rather inaccessible to folks who just want to know which cards to carry. So my thought is to pair my recommendations with what I see as basically two reasons that one gets into using credit cards to improve their travel experience:

Reduce your travel costs
Have a great experience while traveling

I'll break it down below. Pick the card(s) that offer the most value in the ways you value most with the disclaimer from me that I am writing this to be as accessible as possible, and am generally not paying much attention to value you can get from transferring points to airlines or messing around with more complicated schemes to get more value.

By the way, if you decide to apply for any of these, do use the link I've provided here. Wine:Thirty Flight will earn some bonus points (on most) that will help support the site. Thanks!

Best card to reduce your travel costs

The first (and in my opinion, the most important) reason to use travel-oriented credit cards is to take advantage of point earning to reduce (or eliminate) your travel costs. The basic model is that each card offers a particular number of points earned per dollar spent on specific categories (i.e. travel, dining, gas stations, etc); cardholders accrue and redeem those points in lieu of paying actual money for travel. Points are a little abstract for most consumers because their value differs between card issuers, so I use a measure I call "Value Per Hundred" (VPH) that basically tells you how many dollars worth of travel you get per hundred dollars spent on the card. It helps me compare apples to apples.

Winner: Chase Sapphire Reserve (apply here)

I see many of these cards "in the wild" for very good reason: It's the best, most versatile, easy to use card for earning travel on most airlines. Its minimum Value per Hundred (VPH) of $4.50 back for every $100 spent on travel and dining, and $1.50 back for every $100 spent on everything else means that you're basically getting 4.5% back every time you throw the thing down to pay your bar bill or buy your ticket.

3x Chase Ultimate Rewards points per dollar spent on all purchases for travel (airlines, hotels, rental cars, trains, cruises, Uber and Lyft) and dining
1x points per dollar spent on all other purchases
Redeem points for either $0.015 (thats 1.5 cents per point) towards travel booked through Chase
The first $300 spent each year on travel are credited back to your account
Total annual out of pocket is $450 (annual fee) - $300 annual travel credit = $150 before accounting for all other benefits and point earning

What makes this card so special, though, is that you can also pick up some combination of the Chase Freedom Unlimited (apply here), Chase Freedom (apply here), and Chase Ink Business Preferred (apply here) cards in addition to the Reserve. Each offer bonus points in different spending categories, and all the points can be combined into your Reserve account to redeem at 1.5 cents per point or transferred to airline and hotel partners. Having all of these is how I earn 5x points / $7.50 VPH on cell phone / Internet / cable / office supply stores (including gift cards) and special bonus categories that change every quarter (e.g. department stores at Christmas), 3x points / $4.50 VPH on all dining / travel / shipping / Internet / cable / cell phone, 2x points / $3.00 VPH on gas stations, and 1.5x points / $2.25 VPH on literally all other purchases. The Chase Ink Business Preferred is available to individuals, and also offers up to $600 per claim in cell phone theft or damage when you use it to pay your bill (and get 3x points in the process).

Runner Up: American Express Platinum (apply here)

The AMEX Platinum actually earns more points (5x to be exact) for airfare and hotel purchases than the Chase Sapphire Reserve, is less well rounded as a point earner, and a bit more complicated to get your maximum benefit (see notes below). Its minimum Value per Hundred (VPH) is the best in the business for travel expenses at $5.00 back for every $100 spent on air and hotel, but only offers $1.00 back for every $100 spent on everything else.

5x AMEX Membership Rewards points per dollar spent on flights booked directly with airlines or on amextravel.com
5x points per dollar spent on prepaid hotels booked on amextravel.com
1x points per dollar spent on all other purchases
Redeem points for either $0.01 (thats 1 cent per point) towards travel booked through amextravel.com
First $200 worth of fees on an airline of your choice (you pick the airline when you get the card and the start of each year) are credited to your card each year (what counts as a "fee" is different airline to airline, but with American Airlines -- my choice each year -- I get the reimbursement for checked baggage, choosing my seat, paying for an upgrade, and paying for meals and higher end drinks in the American Admirals Club lounges)
First $15 dollars per month Jan - Nov and first $20 per month in December spent on Uber rides are credited to your card
Total annual out of pocket is $550 (annual fee) - $200 annual airline fee credit - $200 annual Uber credit = $150 before accounting for all other benefits and point earning

Honorable Mention: American Express Hilton Honors "Aspire" (apply here)

This new card (launched in early 2018) is a partnership between American Express and Hilton Hotels, and is extraordinarily lucrative for those who often stay at Hilton properties (including Hilton, Embassy Suites, Hampton Inn, Doubletree, Garden Inn, and others). Its minimum Value per Hundred (VPH) is a huge $20.40 back for every $100 spent on Hilton stays, $4.20 back on flights / car rentals / U.S. restaurants, and $1.80 back for every $100 spent on everything else. The catch is that you really can only redeem those returns on Hilton stays, so the card is basically worthless for those who don't regularly use Hilton Hotels, thus giving it at best an honorable mention on this list.

14x Hilton Honors points per dollar spent on Hilton stays + 20x points for being a Diamond member
7x Hilton Honors points per dollar spent on flights booked directly with airlines or on amextravel.com, car rentals, and restaurants in the U.S.
1x Hilton Honors points per dollar spent on all other purchases
Hotel points are notoriously hard to value, but The Points Guy estimates that Hilton points are generally worth about $0.006 (that's .6 cents per point) when used to book future stays at Hilton Hotels (as of April 2018)
First $250 worth of fees on an airline of your choice (you pick the airline when you get the card and the start of each year) are credited to your card each year (what counts as a "fee" is different airline to airline, but with American Airlines -- my choice each year -- I get the reimbursement for checked baggage, choosing my seat, paying for an upgrade, and paying for meals and higher end drinks in the American Admirals Club lounges)
First $250 dollars per year spent on purchases made during a visit to a resort found on Hilton.com/resorts are credited back to the card
Total annual out of pocket is $450 (annual fee) - $250 annual airline fee credit = $200 before accounting for all other benefits and point earning (note that I am not counting the resort credit in this calculation because the locations are fairly limited)

Best card to have a great experience while traveling

The second reason to use travel-oriented credit cards is to take advantage of the great benefits some of them offer in making your travel experience better, generally by giving the cardholder complimentary access to airport lounges. These lounges offer the benefit of a respite from airport crowds (when they themselves are not too crowded), and usually fall somewhere on the spectrum of complimentary snacks and basic drinks to complimentary full meals with equally complimentary stocked bars.

Winner: American Express Platinum (apply here)

The Platinum is the undisputed king of airport lounges, offering a particularly elevated lounge experience for those looking to maximize comfort, convenience, and complimentary food and drinks when they travel. It blows everything else out of the water.

Complimentary access to American Express Centurion airport lounges -- the best in the United States -- and their excellent gourmet meals, full bar, and compelling wine lists at a growing list of airports including New York LGA, Philadelphia, Miami, Dallas DFW, Houston IAH, Las Vegas, San Francisco, Seattle, and Hong Kong (coming soon to New York JFK and Denver) as of April 2018
Complimentary access to Delta Sky Club airport lounges on the same day that you are flying Delta Airlines
Complimentary access to over 1,000 Priority Pass lounges at airports around the world (some are great, others are mediocre)
Total annual out of pocket is $550 (annual fee) - $200 annual airline fee credit - $200 annual Uber credit = $150 before accounting for all other benefits and point earning

Runner Up: Chase Sapphire Reserve (apply here)

While the Chase Sapphire Reserve isn't nearly as generous on lounges across the board as the AMEX Platinum, it does offer unlimited guests in the Priority Pass lounges (whereas AMEX caps your guests and charges you a fee to bring in folks beyond your guest limit).

Complimentary access to over 1,000 Priority Pass lounges at airports around the world, but with unlimited guests
Total annual out of pocket is $450 (annual fee) - $300 annual travel credit = $150 before accounting for all other benefits and point earning

Honorable Mention: Citi AAdvantage Executive World Elite Mastercard (apply here)

It's rather a tough call on Chase vs Citi AAdvantage here, but in the end I can't give Citi more than an honorable mention because it's really only useful to frequent travelers on American Airlines, and to those who regularly fly through airports where American has a large enough presence to warrant a lounge.

Complimentary membership to the American Airlines Admirals Club for the primary cardholder (membership allows you to use the lounge -- and the complimentary snacks and drinks it offers -- regardless of whether you are flying on American that day)
Complimentary access to the Admirals Club for all authorized users (access allows you to use the lounge and its amenities on days you are flying American)
Priority checkin and priority boarding privileges on American Airlines flights, first checked bag free for you and up to eight travel companions, too!
Total annual out of pocket is $450 straight up, which I easily make up in complimentary food and drinks given how often I fly American

Best overall card, rank ordered according to... me

Chase Sapphire Reserve - Colloquially dubbed the CSR, this is really the flagship, foundational card that everyone should have in their wallet. It's particularly well suited to folks who love to travel, dine out, and who live in more urban areas. It's extraordinarily well rounded, with good point earning rates towards free travel, travel insurance* that will back you up in a pinch, a great lineup of airport lounges around the world, and a lineup of airport lounges in the U.S. that is growing more respectable by the month. I can think of very few readers of this blog who should not have this card. Apply.

*Trip Cancellation / Trip Interruption Insurance, Auto Rental Collision Damage Waiver, Baggage Delay Insurance, Trip Delay Reimbursement, Roadside Assistance, Lost Luggage Reimbursement, Travel and Emergency Assistance, Travel Accident Insurance, Emergency Evacuation and Transportation, and Emergency Medical and Dental Benefit

American Express Platinum - The AMEX Platinum is well suited to folks who love to travel, and who live in more urban areas. Its access to Centurion Lounges, Delta Sky Clubs, and Priority Pass airport lounges around the world make it the absolute top-of-the-line card for those who most value the comfort, free food, and complimentary drinks that each lounge has on offer (to varying degrees of quality). The Platinum offers superior point earning on travel and below average point earning on everything else, the aggregate of which I think is edged out a bit by the much more well-rounded (thus easier to use) Chase Sapphire Reserve. Apply.

Citi AAdvantage Executive - This is one of those cards that I'd rather not be paying for, but can't deny that the benefit of American Airlines lounge membership for me / access for authorized card holders makes it far and away worth it given how often I fly American. United and Delta don't offer anything close. Apply.

American Express Hilton Honors "Aspire" - This is undeniably a great card, with superior point earning above all other things, for those who spend a lot of time staying in Hilton (and related brand) hotels. It also nets you the same Priority Pass lounges as the CSR and Platinum, though I rank it below those two cards because it is fundamentally useless to those who aren't committed to staying at Hiltons. Apply.

jetBlue Plus - The dark horse candidate on the list, for it didn't make either of the reduce costs or great experiences lists above, the jetBlue Plus Card is in my opinion the single best travel card with a sub-$100 annual fee ($99 per year). It's obviously only valuable to those who are able to use jetBlue (America's best airline?) to get to where you're going (strongest in the eastern United States and Caribbean), but it offers a generous 6x points on all jetBlue purchases, 2x points at restaurants and grocery stores, and 1x points on all other purchases in addition to a free first checked bag, and 5,000 jetBlue bonus points each year just for possessing the card (approximately a $65 value). That works out to VPH of $7.80 back per every $100 spent on jetBlue, $2.60 back per every $100 spent on restaurants and grocery stores, and $1.30 back per every $100 spent on everything else. Total annual out of pocket is $99 (annual fee) - $65 (value of annual 5,000 point bonus) = $34 before accounting for all other benefits and point earning. Apply.

Bottom Line

So which of these cards do I have? Surprise - all of them. I've done the math on them, and their annual fees are so well offset by the benefits I receive from them that their aggregate effect (in spite of the steep annual fees on most of them) actually serves to save me money in the end... and make my travel experience far more enjoyable in the process. I encourage you to do the math and weigh the benefits for yourself (i.e. don't sign up for the Hilton card if you don't stay at Hiltons), but this list above is where I'd start. Good luck!