I wasn’t happy about the prospect of flying right home.

I was planning to fly up to Chicago from Jacksonville with my girlfriend to accompany her for a grad school interview and had booked our flights on Southwest. For the flight up, I used Southwest gift cards purchased using our American Express Platinum Cards’ $200 airfare fee credits (she has one, too). A total cost of $156 each for the leg up was more than I was happy with, but “free” from the right point of view, thanks to the fee credit.

The flight home was a bit less, at $138.10 each. However, we’d wiped out most of our free credit with the flight up, meaning this flight would require almost $200 out of pocket. I went ahead and booked the fare, but the cost of our flights up and back didn’t sit well with me.

To most airfare consumers, these prices might have seemed fairly reasonable. Of course, you and I aren’t normal airfare consumers. I hadn’t paid more than $100 for a Southwest flight – and normally no more than $5.60 in taxes along with a few thousand points – in years, and this didn’t seem like a good time to start.

A great thing about flying with Southwest is that the airline doesn’t assess any change or cancellation fees on its fares, even when they fall into the cheapest, “Wanna Get Away” category. While “Anytime” and “Business Select” tickets are fully refundable, even “Wanna Get Away” fares may be cancelled in exchange for credit good for 12 months toward future flights. This applies to both cash and points fares, meaning if a lower price comes along after booking, you can profit by simply canceling and rebooking the same seat at the lower price.

I waited for a few weeks to see if the fare would fall in either direction and was disappointed to see each leg either refuse to budge or actually increase in price. I figured we needed to stick with the plan, until an idea struck:

Chicago…there was something about Chicago I was forgetting.

The Rise of the Empire Builder

You could say the idea hit me like a train. My girlfriend loved the brief train ride we took last year from Washington to Philadelphia and I’d been intrigued by a number of Amtrak’s specialty routes since I wrote a chapter on their Guest Rewards loyalty program for the PointsAway Book. It just so happened that two of these routes originated in Chicago, and one other made for a compelling extended journey following a layover.

Rather than flying right home, why not take advantage of the fact that we were already in Chicago and catch one of these Amtrak routes west, flying home shortly after arriving at our final destination?

Empire Builder is the route that immediately came to mind. Loosely following the trail of Lewis and Clark, Empire Builder winds from Chicago through Wisconsin, Minnesota, North Dakota, Montana and Idaho before ending up in either Seattle or Portland, following a split around Spokane.

The other possibility was California Zephyr, which heads through Iowa and Nebraska on the way to Colorado, through the Rockies to Utah, Nevada and ending in San Francisco.

One question I had was whether it would be possible to tie either of these routes to a third possibility, the Coast Starlight. I’d heard that this route, which hugs the Pacific ocean all the way from Seattle to Los Angeles, was one of Amtrak’s finest, featuring the last remaining Parlour Cars in their fleet. Plus, thanks to Amtrak’s unique award zoning rules, our trip would require the same number of points whether we ended our journey in Seattle, Portland, San Francisco, Los Angeles or anywhere else up and down the West Coast.

Amtrak Guest Rewards: A Primer

Amtrak’s Guest Rewards program offers the best of both worlds when it comes to award redemptions. Every last seat, roomette and bedroom and Amtrak routes can be booked using award points, and a flat rate is required regardless of the cash cost for the same ticket. That means, like Southwest, there are no blackout dates to worry about, while like American, the same number of points are required per region, even if the cash cost might normally be very expensive.

As I mention in the book, perhaps the most compelling award possibility on Amtrak is for a roomette on a long journey. Roomettes provide sleeping quarters for either one or two passengers for a low flat rate, and even include both passengers’ meals throughout the journey!

Amtrak award prices are based on how many regions your itinerary travels through. They split the country vertically into three main regions and one subregion for the Northeastern United States.



Our journey, from Chicago to somewhere on the Pacific Coast, would be a Two Zone Redemption regardless of where on the Pacific Coast we ended our journey. A two zone roomette redemption can be had for just 20,000 points. These points can be transferred in to Amtrak’s program from Ultimate Rewards, meaning it was easy for me to swing a redemption even though I’d only ever ridden with Amtrak once before!

Sketching Out the Trip

Determining our final destination became a game unto itself. In order to book an award ticket, you must be able to find a cash ticket on Amtrak.com for the same itinerary. Overnight layovers are typically prohibited. That meant, thanks to route timing, taking Empire Builder and connecting to Coast Starlight would be possible, but only if we connected in Portland instead of Seattle. Furthermore, the same trip would not work in reverse. Booking a ticket on California Zephyr would be no trouble, given that we’d be riding just one route from beginning to end.

We ended up opting to take Empire Builder from Chicago to Portland, then connecting to Coast Starlight approximately four hours later to continue our journey south. Though there were dozens of potential stopping points thereafter, we focused on San Francisco and Los Angeles. The route was scheduled to arrive in San Francisco (technically across the bay in Emeryville, with a free connecting bus to a number of locations in the city) early in the morning and arrive in Los Angeles late at night. By stopping in San Francisco, we could enjoy a full day on the ground without paying for another night at a hotel, as we’d have to in Los Angeles. That made San Francisco the better play.

Getting Home

I checked to make sure flights would work out of San Francisco and was happy to find Virgin America was holding a sale expiring later that night. I love Virgin America, but the opportunities to fly with them are slim, given my location in Jacksonville. However, I figured out a clever trick: we could fly Virgin America to Fort Lauderdale, then race to a separate JetBlue flight home from Fort Lauderdale to Jacksonville about 90 minutes later. JetBlue is new to the JAX-FLL route and is offering tickets as low as $34 each way as a promotion.

Booking the Trip

The route was settled: we’d take Empire Builder from Chicago to Portland, then Coast Starlight from Portland to San Francisco. We’d spend one night in San Francisco, then head home on a redeye with Virgin America, from SFO to LAX to FLL, then on JetBlue from FLL to JAX.

First, I called Amtrak to confirm I could book the route I was seeing online, which looked like this:



A bus would take us to Fisherman’s Wharf, just a few blocks from the Hyatt where we’d be staying for the night, also for free thanks to an award redemption! Note the cash price: this booking would have cost a whopping $1,565 as a cash fare for two passengers, but because a roomette was available to book, points could be used instead at the flat rate! The Amtrak rep confirmed we could make this booking, and I immediately transferred in the 20,000 points necessary from Ultimate Rewards. Amtrak redemptions come with no taxes or fees, meaning this redemption was truly free!

We used Elevate points, transferred from our Membership Rewards accounts, to cover the Virgin America fares. Even though this transfer requires 2 Membership Rewards points for 1 Elevate point, an extremely low rate of 6,233 Elevate points per seat made this a fair enough proposition, especially given how much better the Virgin flying experience typically is compared to our alternative option of US Air.

I simply paid for the JetBlue tickets, given how cheap they were:



A Unique Value

In the beginning, we planned to simply fly home from Chicago on Southwest for a total cost of $276.20 for two passengers. In the end, we went from Chicago to Portland and down to San Francisco, spent a night by the bay and flew home for a total cost of $79.20!

I repeat: we were able to add on a crazy, four day adventure across the country to our previous itinerary while spending nearly $200 less than simply flying home. That’s the kind of trip I get excited about: one where it’s possible to earn thousands in additional value and see things I’d never see otherwise while still spending less than I would have with a more conventional mindset. In the days to come, I’ll share more thoughts from the trip, so stay tuned!