I will be very honest with you guys, I am not a fan of Southwest, as opposed to Jeremy who is a diehard Southwest Fan. But after more than 5 years since my last experience on the LUV carrier, a great sale brought me back to give them another try. I was heading back to Florida for a few months again to skip the normally frigid winters of Chicago and spend more time with my family as I continued to work from home in Fort Lauderdale - one of Southwest’s main hubs.
Founded in 1967 by Herb Keller in Texas, Southwest was one of the pioneers of the low cost carrier concept. It has since grown from Dallas-Love Field to over 700 aircraft and 4,000 daily flights and one of the main domestic carriers in the US. Southwest famously operates an all Boeing 737 fleet which helps keep cost down and pilots trained across the whole fleet while also focusing on their famous LUV hospitality.
When booking any flight I always check my way through carriers not sold on third party platforms such as Google Flights, and while I find my fares that way, I always recommend purchasing directly with the carrier. This time I found that Southwest had a great deal on their ‘Wanna Get Away’ fares to Fort Lauderdale and decided to give it a shot. I booked directly on the Southwest website and after taxes and fees, my total came out to $45 one way. I netted a total of 90 points at 2x points per dollar spent on travel with my Chase Sapphire Preferred.
As the pandemic persisted across the US, it was time for me to come back to Chicago after being home in Florida for nearly 3 months. Growing up in Fort Lauderdale, a JetBlue focus city, flying them is as common as flying Spirit for us locals and is a household name.
JetBlue was founded in 1988 by industry legend David Neeleman and commenced operations in 2000 with a flight from Buffalo, NY to Fort Lauderdale, commencing a long relationship with the South Florida region. JetBlue has distinguished itself mostly on the east coast of the US for its low cost carrier business model, but with features such as satellite TV and high quality snacks. This was further elevated in 2013 when they introduced their revolutionary business class cabin: Mint, which Jeremy flew earlier this year. With this, JetBlue cemented its place as a top US carrier and has become a beloved company along the Atlantic Coast.
As mentioned in my prior reviews, this trip home was originally supposed to be a 3 week long round trip with Spirit, who I did fly on the flight down. However being around my family and dog was quite great in these difficult times and as I got used to not doing my own laundry again, I extended my trip 3 times… At first, I canceled and rebooked my original return on Spirit for 3 weeks later, then cancelled again and booked with jetBlue 4 weeks later in Blue Basic - jetBlue's version of Basic Economy; which allows one carry on, but restricts with added fees for seat selection, lesser mileage earning, later boarding, and inability for cancellation (although this is temporarily suspended during the pandemic). Then due to Hurricane Isaias hitting Florida and delaying our beach trip to the Residence Inn Tierra Verde, I ended up extending my trip one more week for good measure.
The final breakdown was as follows; I first booked my FLL-ORD flight for Sunday, August 9 for $25, an absolutely ridiculous steal for a route where I have paid $450 round trip before. However, due to the aforementioned hurricane, I extended my stay and a week prior to departure and rebooked my trip to Sunday, August 16 paying an extra $12 for the fare difference. Thus I paid a total of $37 for this one way fare in Blue Basic with my Chase Sapphire Preferred earning me a whopping total of 74 points.
As part of a last minute trip to Wine Country with my, specifically to the Hyatt Regency Sonoma, we had the opportunity to to experience what travel would be like in the time of COVID. As it turned out, and was also expected, there was quite a bit about the act of flying that had changed from the past.
Personally, we selected Southwest for a number of reasons - the primary being that it is our preferred and most trusted carrier. Beyond that, we appreciated that they had committed to a reduction in capacity and clearly outlined their commitment to cleanliness.
Beyond the reasons stated above, we also selected Southwest because of price. Even at the last minute, we were able to snag our outbound flight for $79 and our return one for $149 on Southwest.com - the only place to book flights on Southwest.
I booked mine using cash and TravelBank Funds - I often watch flights after booking them to see if they drop, and if they do I modify them free of charge and get the difference in fare back to my Rapid Rewards Account. Because of this, I owed just $30 in cash for the outbound flight, so I booked using my American Express Platinum hoping it would be reimbursed from my travel credit - it was! So essentially, my outbound flight was free, but by using my American Express Platinum, I also earned 5x points per dollar on airfare or 895 Membership Rewards Points.
My mom booked her flight using the stockpile of Rapid Rewards Points that she’s Earned with her Southwest Rapid Rewards Premier VISA Card, meaning her flight cost just $5.60 in government fees each way. We both earned 1,276 Rapid Rewards Points by crediting these flights to our accounts.
Having grown up in south Florida near Fort Lauderdale International Airport (FLL), Spirit Airlines was a household name as they were, and continue to be, one of the largest operators out of my hometown hub. Thus, I have always had a soft spot for the infamous ultra low cost carrier and their now bright yellow jets.
Starting in 1964 as a trucking company, it wasn’t until 1992 that the then charter carrier became a scheduled passenger airline and started offering flights from Detroit to Atlantic City, two cities that still play a crucial part of the Spirit network. Originally operating as a low cost carrier, even offering business class known as SpiritPlus, it wasn’t until 2007 that we saw Spirit transition into the ultra low cost carrier that we know and either love or hate today. The changes came swiftly and led the way for what other airlines of all price ranges could offer, charge for, or get away with. In 2010 they became the first US carrier to charge for carry-ons, which has become a norm with many carriers now. Other changes from ‘The Big Front Seat’ larger seats, charging for printed tickets, and more became the norm and their most argued upon aspects. However I am a strong believer that if you do your research and travel with the bare necessities, they are a great carrier to use for cheap flights around the US, or ‘Bare Fare’ as they have coined it.
For me this trip was very last minute, I had been wanting to go home during the pandemic to spend time with my family I don’t see often; however, with a pandemic it can be a double edged sword for all involved. As things were calming down and I was still working from home I decided to go for it and booked my flight 3 days prior to departure. Booking on Spirit is quite simple, and their fares appear on most 3rd party search engines making it easy to compare with other carriers on the same route. After checking a few sites Spirit was by far the cheapest carrier and had a convenient schedule for me. I booked directly on the Spirit website, and after many ads for add-ons and confirming I wouldn’t need a carry-on, seat selection, rental car, or hotel, my total came out to $107.09 roundtrip. I netted a total of 216 points at 2x points per dollar spent on travel with my Chase Sapphire Preferred. With Spirit it is crucial to do your check-in as fast as possible 24 hours prior to departure to get a good boarding zone and seat placement if you did not pay for such prior.
I am a United Airlines fanboy - my first leisure international flight was on a United Boeing 757 from New York to London, and my first aircraft collectable was a Continental Airlines Boeing 777-200. Thus, naturally, when flying from my home base, also United’s largest hub, I have a favorite.
United began operations 94 years ago as a postal service carrier in Idaho. Continental also began around the same time by the same man as a postal carrier in Texas. Both carriers eventually grew to become some of the largest and most crucial carriers in the US after deregulation. In 2010, United Airlines acquired Continental Airlines in the form of a merger. Headquartered in Chicago, IL, modern day United is the 3rd largest carrier in the world with a fleet of over 800 aircraft serving over 300 destinations from 8 hubs, as well as a founding member of Star Alliance.
United began offering extra legroom in Economy in 1999 as the only US carrier to offer separate Economy rows with extra space at a premium price, and would continue to be the only through the early 2000’s - although many carriers featured more legroom throughout the cabin. From there its introduction began ramping up across the mainline fleet; meanwhile, Premium Economy became the hot topic of the 2010’s. In 2015 we saw the branded EconomyPlus product introduced across the Boeing 777 aircraft as well as post merger with Continental on all legacy Continental aircraft. EconomyPlus is now a standard sight within the fleet and includes extra legroom, priority boarding and easy exiting of the aircraft due to its forward location.
This is where this trip got interesting, I was not originally booked on United for this leg, I was actually booked on Spirit Airlines, a carrier I have flown plenty as a Fort Lauderdale native - their home base. My original flight was on Friday, March 6th at 8:10 PM, perfect for after work. However around 1:00 PM that day I received a notification that my flight was cancelled due to technical issues with the inbound aircraft. As you can imagine, I was in a bit of a panic, I needed to get to Dallas that evening and this was the first time I ever had a flight cancelled. I reached out to Spirit on social media and through the phone, then suddenly I got an email from Spirit rebooking me on a set of American Airlines flights connecting me through LA and arriving in Dallas the next day at 6:00 AM. Now, flying a red-eye on economy for a weekend trip to the other side of the country with a layover and back did not sound ideal. So I asked what else could be done and was told to contact the Spirit desk at O’Hare but then proceeded to give me the number of the actual airport, which led nowhere.
After being told the only way to change my flight would be to show up at O’Hare and work it out at the desk, I asked to cancel my flight and surprisingly received a full refund quite fast. I was now flightless with a return ticket from Dallas already booked. So I took to my favorite app, the United app, and checked award travel, to my pleasant surprise there were seats on a 8:20 PM Non-Stop to Dallas in Economy. A few clicks and I secured myself a seat on my go to carrier out of my favorite O’Hare terminal in less than 5 minutes. Given this was the beginning of the Coronavirus’ arrival to the US, seats weren’t as hard to find, however I would not recommend booking flights for a trip so last minute.
I booked this flight for 15,000 MileagePlus Miles, valued at $195, and $5 of taxes and fees. After a long trek to the airport, I arrived at my gate exhausted and in the last boarding group which felt like just too much. So I went back on the United app and purchased an upgrade to EconomyPlus for only $27 which came with an upgrade to Boarding Group 3. Due to the nature of mile redemptions, for this trip I did not earn any points.
I found myself needing to go to Los Angeles at the last minute for a business trip. Given that I was traveling on the company dime, I had to book through our client’s preferred carrier - American Airlines. I’ve had several negative experiences with American on this route and was interested to see how it would go this time. In this piece, I’ve written about both legs of the journey - a tale of two flights, if you will - as there were stark contrasts.
Given this was a business trip, we booked our flights utilizing our company’s corporate travel agent, and then selected our seats as usual on American’s website. I credited these flights to my British Airways account, as I do all American flights as British Airways is a transfer partner of Chase Ultimate Rewards.
Many reading this will think I’m crazy when I explain how this flight came to be, and that I voluntarily opted for a 9 hour layover in Seattle to go visit my sister in Denver. For aviation geeks, this probably sounds like the butt of a bad airline joke about Delta always taking you through Atlanta, but here’s how I got to this point: flight prices between Chicago and Denver were astronomical for the dates that I needed to go, then it dawned on me that I still had a $100 Credit on Alaska Airlines, an apology for rebooking me on another flight in the past, so I gave it a look. Lo and behold, I could save money over the competition, and give myself an awesome day exploring Seattle - one of my all time favorite cities! Plus there was the added perk of being able to surprise my sister with bagels from Seattle Bagel Company, and to have fish and chips and a Rainer for lunch at Pacific Inn Pub - one of my favorites!
As it turns out, good things do in fact come to those who go! As I was exploring the city, I received an email from Alaska that I’d been given a complimentary upgrade to First Class due to my MVP Status with the airline.
As I mentioned above, I utilized a $100 travel credit as a portion of this booking- which in turn made this far and above the cheapest option to get to Denver. I booked this flight directly on www.alaskaair.com, but Alaska also markets and sells its flights through online travel agencies. I selected a Main Cabin fare, knowing that I could select a Premium seat for free at Check-In with my MVP status. The grand total for my flight from Chicago to Seattle to Denver was $194, which again, was less than both United and Southwest were selling their nonstop flights for on this date. I booked with my American Express Platinum Card, for its 5x Points on Airfare earning, and banked 970 Membership Rewards Points, in addition to the 4,116 Alaska MileagePlan Miles that I earned - it should be noted that because I was given a complimentary upgrade, I did not receive a First Class earning multiplier.
In 2017, Alaska introduced Premium Class aboard it’s Boeing 737 Fleet. The product promised early boarding, 4” of extra legroom, elevated snacks and complimentary alcoholic beverages. In addition, Mileage Plan Elites would be eligible for free upgrades - others can purchase these seats at an additional cost. After its acquisition of Virgin America, these same standards migrated over to the Airbus Fleet - some of whom are retrofit, while others are simply a rebrand of what was once Main Cabin Select.
We booked this flight as part of a longer three leg journey from Chicago to Portland, Portland to Los Angeles, and Los Angeles back to Chicago as a means of maximizing the value of the annual Companion Pass that’s a perk of my Alaska Airlines VISA Card. As such, the combined total of our two tickets, including the Companion Pass, was $576.99 - coming to a total of $288.49 per person, or $96.16 per flight - a great value in my book! To maximize Alaska Mileage Plan Miles, which are some of the most valuable in the industry, we booked using my Alaska Airlines VISA card netting three miles per dollar and a total of 1,731 miles. In addition, this leg of the journey earned 1,745 base miles and 873 MVP bonus miles for a total of 2,618 miles.
When headed to the Lone Star State, why not fly with the product of it - Southwest Airlines? From Chicago, Southwest operates exclusively out of Chicago Midway, the city’s secondary airport, and while not nearly as large as O’Hare International it has enough traffic to have earned the moniker “the busiest square mile in the world.”
As with all Southwest flights, we booked directly with the airline on www.southwest.com - Southwest is not bookable through any online travel agents and will typically not show up in travel search engines such as Google Flights. Given this was a family trip, we booked utilizing my parents' stash of Rapid Rewards Points that they had accrued through the opening of a new Southwest Rapid Rewards Premier VISA Card - long a contender for my wallet as well.
In looking for a proper flight back from a hybrid New Year’s Eve and Conference speaking trip, I was immediately struck by how high rates were to fly back to Chicago on New Year’s Day. That’s when it dawned on me, this is a perfect opportunity to make use of the stockpile of points that I’d been collecting! When poking around investigating our options, we found that we could snag a First Class fare on Delta for just a smidge more than in the Main Cabin, and thus we landed a seat on our flight home!
Booking a flight on New Year’s Day is no small feat. Passenger demand is high, and so are rates - which is how we arrived at using points to book this flight. We booked our award flights through Virgin Atlantic’s Flying Club by transferring Chase Ultimate Rewards points at a 1:1 ratio. Each ticket came out to 22,500 Virgin Atlantic Flying Club Miles - valued at $337, which we viewed as a steal since this was less than the cash rate in Main Cabin, and far lower than the four figure price that First Class was going for. I already had miles in my Virgin Atlantic account, so I only had to top it off with 14,000 Miles - meaning my flight really only cost $210! We completed the transaction through Virgin Atlantic, then migrated over to Delta’s site to select our seats.