What It Was Like Taking A $58 Round-Trip Flight From Chicago To Florida

58dollars
ADVERTISEMENT

This week I spent four days in warm and sunny Tampa, Florida. While I was officially there for the 2023 Florida RV SuperShow, it was also just nice to get away from the gray, cold, gloomy weather of Illinois. To get there, I took the cheapest possible round-trip flight that I’ve seen in my entire life. Somehow, I scored a round-trip flight aboard Frontier Airlines for just $58, and — looking back — it now just feels so wrong.

Despite my love for all things aviation, I’ve been flying airplanes since just late 2016. Up to that point, I’d just never needed to fly. If I traveled, it was almost always via the driver’s seat of an SUV, likely towing a camper somewhere. On October 20, 2016, that changed when I boarded my first-ever plane flight, a 7:45 AM trip aboard “Fallon The Falcon,” a Frontier Airlines Airbus A321 that had taken its first official trip just four months prior.

20161022 071329
Mercedes Streeter

It was a truly magical flight for me, and even further cemented my love for commercial aircraft. My very first flight, which was from Chicago’s O’Hare International Airport to Los Angeles International Airport, cost me just $60. The next year, I took a flight aboard a Spirit Airlines A320 to Denver for just $31.

Since then, that Spirit flight held my personal record for the cheapest flight. That flight alone is pretty boggling when you think about it. That $31 ticket that got me 900 miles westward cost me significantly less than it would have cost me to fuel up a small sedan for a trip of the same distance. Heck, $31 is cheaper than what you’d pay to take a Greyhound or a train!

30cc9558da4dfbfc98bc8172fb9abc74
Mercedes Streeter

In the almost six years since that flight, I’ve never come close to that price on a plane ticket. One time I paid $210 to get crammed into a Bombardier CRJ-200 for just a touch over an hour. On another, I somehow found myself paying $370 for a red-eye aboard Spirit. To this day I think that was my worst-ever flight. And that was $370 with zero of Spirit’s microtransactions. At least I got a free margarita on that plane; I’m still confused as to why the flight attendant was giving everyone free booze that night.

Even in the middle of the pandemic, when air travel took a clobbering, I still paid at least $120 for one-way flights. So, when it came time to schedule my flights for the RV show, what David Tracy found was shocking.

Screenshot (241)

That’s not a doctored photo. We found a round trip from Chicago’s Midway International Airport to Tampa International Airport, a distance of about a thousand miles, for just $58. Yes, the flight was aboard Frontier, but the cheapskate in me couldn’t resist. That’s just $29 per flight —a new record for me! I had our Galpin travel agent book it.

For full-frontal honesty, the travel agent did pay for basically every upcharge that Frontier had to offer. They paid for priority boarding, a specific seat, a carry-on, a checked bag, and other add-ons that were unnecessary. If you’ve never flown Frontier before, yes, the airline charges you for all of that stuff. Don’t think the charges end there, either, because the airline will even charge you to drink some water on your flight. Frontier is so cheap in how it runs that its planes don’t even have WiFi.

20230116 094231

 

I travel really lightly. Unless I have to bring something big with me (like motorcycle gear), I pack my purse to the gills and take just that. If it can’t fit, it won’t fly. Since the Galpin people paid for the checked bag, I decided to at least use it. Amusingly, the total after the add-ons came to about $300. This was still $50 cheaper than the base fare for a round-trip on Spirit and about $120 cheaper than a round-trip on American Airlines.

These flights were both rough and also two of the best flights that I had ever taken. They were rough because I mean, did you see those departure and arrival times? I had to wake up at 3 AM to make my departure flight to Tampa, and I didn’t arrive back at Midway until nearly 1 AM last night.

20230119 222221

However, departing and arriving at those times also meant that the planes on both flights were ridiculously empty. The flights were so empty that most people had a row all to themselves and the only people sitting next to each other did so on purpose. Some passengers used this to their benefit by laying down and enjoying a nap. Me? I kicked back at my window seat, relaxed, and pointed all of my row’s air nozzled toward me. There were no crying kids, no smelling other people’s farts and the lack of people made the plane feel so much bigger.

20230116 082539

I could tell that the flight attendants were more relaxed, too. After all, they didn’t have a whole planeload of people to deal with.

Flying like this was so relaxing that I might just intentionally choose weird times from here on out. It had another benefit, too, and it’s that I got to spend more time in Florida outside of the RV show. I didn’t realize it when I first landed, but I actually had enough time to scratch off a road trip bucket list item. I’ve always wanted to drive on Florida’s Overseas Highway and the Seven Mile Bridge, both of which which were just six hours south of Tampa.

Pigeon Key
Monroe County Tourist Development Council

I decided against it, thinking that it would be dark by the time I got there. Later, I figured out that I actually had plenty of sunlight. Ah, maybe next time.

Since I didn’t go that far south, I decided to explore within a 100-mile radius of Tampa, and the sights will forever be imprinted in my brain. Florida’s coast is absolutely spectacular, and the state’s bridges–at least the ones I saw–are a marvel. I had to pull over just to take a picture of the Sunshine Skyway Bridge outside of St. Petersburg.

20230116 122129

20230117 190457

I also stopped at a beach, where I took a swim and watched the local wildlife. If you ever find yourself frayed at the ends with stress or wound up tight, just go to your nearest beach or nature preserve.

Sit there and watch the wildlife do its thing; you might find yourself experiencing relaxation that you’ve never felt before.

20230119 181643

Before this trip, I had been to Florida only two other times. My first time in Florida was when I was a kid, and I don’t really remember it. The second time was back in 2014, and I was stuck traveling with now former friends. We never ventured much farther than a mile outside of Walt Disney World, so there wasn’t much exploration. This time, I was by myself and with a rental Nissan Sentra with unlimited miles on hand.

20230116 134851

I put 420 miles on the Sentra, exploring that part of Florida, and I’ve realized why people move to this state. There’s so much to do and Florida’s gorgeous lands and waters can turn even a mundane commute into something beautiful. Sure, the only elevation changes are bridges, but it’s amazing how diverse Florida’s ecosystems can be. California is still one of my favorite places to go for a road trip, but now I have to return to Florida. I still have to see Miami, and the Everglades, and to drive on the Overseas Highway.

20230116 172518

This is all to say that this $58, technically $300 round-trip, is one of the best that I’ve ever taken. It was so cheap that I felt like I fleeced someone. It was so cheap that I joked that the only way it was possible was if the passengers flew the plane. The flight was so cheap that I felt like the plane was going to have to be an old rickety DC-3 flown by Harrison Ford. Instead, it was great, and I used it to create some awesome stories and lovely memories. When you’re choosing flights, if you see a cheap option that has you waking up before dawn, it might be worth taking!

Relatedbar

About the Author

View All My Posts

46 thoughts on “What It Was Like Taking A $58 Round-Trip Flight From Chicago To Florida

  1. As a Miami native, you should definitely visit South Beach and the Keys. Post Card Inn is super fun and the drive to Key west is amazing.

    I’m sure some of us would love to meet up if you do head down this way.

    I think Frontier and their ilk are perfect for shorter flights (5 hours is pushing it) and if you travel light. Great for weekend trips.

  2. I assume these flights were so cheap because they had to move the jet from one airport to another to be ready for a more profitable flight, so they might as well take a few customers while they were at it.

    1. I used to do that when I was commuting from Boston to NYC 3x/week in the 80s. I was working at the WTC and it was a PIA to get back up to LGA to get the shuttle at the end of the day. Instead, TWA had a 747 that they moved from JFK to BOS for an overnight going to somewhere in Europe. It was slightly cheaper, an easier ride to the airport and there were a handful of people on a 747, which was a unique experience!

  3. Last Fall I flew round-trip from LAS-STL on Spirit for a grand total of $29.22. The actual airfare shown on the ticket was $0.01 each way, and the other $29.20 was taxes.

  4. If you can deal with the low cost airlines Mercedes, go for it!

    I’m the reverse at this point in my life (i.e., nearing retirement); I book almost exclusively Delta because I have a lot of FF miles with them and I generally buy 1st class if I can afford it. I can relax better in first as I’m a fairly tall person and don’t fit into today’s economy seats well, and I spent a lot of my 20s-40s flying for work so I paid my dues. 🙂

    I have family in the Tampa area so I go down there every so often. I first started going there in the early 80s and wow, it has changed!

  5. This is a bit like DT’s articles about “How I drove my (insert number here) shitbox from here to there and back again” stories. The insert number is just the starting point and we rarely get to see the ending point.

  6. As a born and raised FloridaMan, who currently resides in the lands just outside Tampa, I wish you’d mentioned that you were on your way down here. If nothing else, I could have recommended a couple of places to chow down at.

  7. I had wanted to go to the RV show to get a sense of what I need to accomplish at the best price possible, but I figured “the world’s largest RV superstore” (Lazy Days) is 5 minutes past the fair grounds, so I passed it up. I look forward to reading your content on your observations from the show. Though if you really want to make an exposé, you should come for the RV show and the Florida State Fair (lots of RVs there, too, but the people watching is SO GOOD).

  8. I recently flew to Utah for a weekend and took a 6:10 flight that I had to get up at 4:00 for, and took a Lyft to the airport for the first time ever because even though I’m two blocks from the CTA and can usually be at ORD security from my front door in 45 minutes (or an hour for Terminal 5), I needed predictability and didn’t want to get up even earlier to make sure I made the right train. But, like yours, the flight was half empty and stress-free.

  9. Merc, if you want to do the overseas highway to the end, plan on at least two full days. First off, just getting through the Miami metro and down to Homestead is a total chore; then, you have several hours getting to the actual end of Florida.
    Once you’re on the “bridges”, it’s slow going. Part of the problem is that there are a lot of Florida drivers down there, for some reason. Every key has a town, and they’re all speed limit 30 because of key deer. If you kill a key deer, expect the same reaction Homer Simpson got when they thought he killed that alligator.
    Also, Key West is awesome, although not as awesome as it used to be, when they let chickens roam the streets. You should spend at least a full day there to fully enjoy it.

  10. What I don’t really understand is why you didn’t just book the super cheap fare and instead paid an additional $250 because… Galpin? Seems like the opposite of the point of this kind of thing. Why pay for a carry-on and a checked bag? And even if the flight wasn’t so empty why would you ever need priority boarding and a pre-assigned seat?

  11. Counterpoint. After flying JSX when I needed a quick one way, I don’t know I’ll every fly anything else if they’re available. Essentially a private jet experience for $149 all in. Taxes, fees, bs charges, everything. Includes 2 bags, and no TSA.

  12. As a former Floridian, it is a GREAT place to visit, not live. One thing I will cherish about my time there is going to the 12 Hours of Sebring for many years. Definitely a lot of rough areas, but walking the paddock as a smashed Porsche GT3 gets pushed past you and watching them replace a transmission faster than you can change oil never gets old. I remember how quiet the Audi R10 diesel was compared to the R8 from previous years. Getting to see the DeltaWing race! For… a little while. Corvette C5.R/C6.R/C7.R and their rowdy V8s. Dang, gonna go look at my over-priced racing programs and reminisce. Go to Sebring! (get your shots first)

  13. And the combination of long distances, cheap flights and the inherently broken nature of Amtrak is why we don’t have European style passenger rail outside of the Acela corridor and I-5 corridors.

    1. We might have a rail system in the UK, but it’s still cheaper and quicker to fly from (eg) Bristol to Glasgow. We invented trains, we’re still shit at them.
      The cheapest option is taking a coach, but that takes 7+ hours.

  14. I am conflicted — I love the idea of being able to jet off cheap. But then you run the maths and those modern airbus A 320s engines burn a litre a second. Each. The A330 engines s do two litres a second. Each
    It is not surprising, if you have ever pointed a compresser blower into a fire (don’t do it at home children) and seen the explosion, just think of how compressed the air is in a jet then it is directed shrieking into a combustion chamber with shower heads of kerosene spaying into it.
    It roars, demands still more air and fuel and the thunder is the noise of the jet.
    Which is how a 1,000 mile trip uses more fuel than an oil fired centrally heated house does all winter.
    Most people don’t give a shit, and an amazing number jet off to Africa, Asia and South America and lecture the poor on energy efficiency. I kid you not.
    So travel is wonderful, flying is a technological marvel, I too am lined up for flying lessons, but if you do it, square your conscience. Somehow.

  15. 15+ years ago there was a small airline that operated out of Dulles called Independence Air. They flew to the major mid-Atlantic and northeast destinations (Boston, NY, etc.) and most of the flights started at $50. Then they went to $75-$125 ($150?). Then they went out of business. 🙁

    It was a shame, as the whole fleet consisted of then-new regional jets – no more turbo-prop puddle-jumpers! And for some reason (likely the proximity to DC) they had prerecorded flight attendant briefings done by James Carville and Mary Matalin.

    Part of the reason for the low prices was that they did not have code-sharing arrangements with anyone else, so if your Independence plane broke down they could not put you on another airline: you were stuck waiting until another Independence platform became available.

  16. Spoiler alert, you are always smelling other peoples farts.

    These airlines are cheap for a reason, roaches pass on them 🙂

    Seriously though, I would pay a couple extra hundred to not fly at the buttcrack of dawn and not spend all day in an airport.

    As far a O’Hare. Anything less that a 1.5 hours between flights, might as well assume you will miss it and book the next one.

    1. The last time I flew internationally I returned through O’Hare. I had about a 2.5 hour layover and thought that would be enough to get through customs and grab lunch somewhere. Ha! It was two hours of standing in line and a 15 minute dash to the boarding door before they closed it. By far the worst customs experience I’ve had at any airport.

  17. I’ve been to Florida many times, but never to Miami, and every time anyone mentions it, they just talk about how the traffic is next level horrendous.

  18. Is it really a $58 fare if in the end you pay $358? Frontier is famous for having cheap fares with lots of fees which make it the same/close as a normal carrier. They have sales for $1 fares too.

    To bring it back to cars, look at the out-the-door price and not the great $299/month for 15 years loan.

    1. “This was still $50 cheaper than the base fare for a round-trip on Spirit and about $120 cheaper than a round-trip on American Airlines.”

      Even with all the add-ons, still seems like a good deal.

    2. The final cost before the add-ons was indeed just $58. The carry-on added about $116 and the checked bag added another $108. The other add-ons got us to that $300 mark, which was still cheaper than American! Even Spirit wanted some decent cash. For reference, we booked this right before the weekend, so too late to catch a good price on one of the big carriers. Clearly, not many people wanted to fly such an early Frontier flight. lol

      I should have told our travel agent guy to book the base flight since I didn’t need the add-ons. I don’t care about boarding zones, am willing to play seat roulette, and I didn’t bring enough to warrant even a carry-on. But I checked something anyway so it wasn’t a total waste of dough.

      1. That’s just a flim-flam scam then. It costs more for a carry-on bag than a person? Sounds like Frontier is a cargo service with a side perk of hauling people along with their bags. False advertising like this is an abomination, and should be illegal. Yet the FTC keeps on allowing companies to make false and misleading statements through advertising. First step – stop allowing fine print and speed talking in advertising.

        1. On the other hand, put on three or four t-shirts, underwear and socks before going to O’Hare. Wear some shorts under your pants. Get to Florida and take all of those things off save one of each and spend 3 or four days enjoying your self. Seems like there are ways to game the system is all I (and Mercedes, I think) are saying.

          1. My go-to air travel hack is putting toiletries and smaller items into a photojournalist’s vest, which has large pockets sized for telephoto zoom lenses and can fit a surprising amount of stuff. It simply comes off at the TSA checkpoint and through the scanner in one piece, then goes back on my body.

            As a garment, the vest doesn’t technically qualify as luggage, but functionally you get an additional unweighted personal item onto the plane and no airline I’ve flown with has ever had an issue with me stowing it in the overhead.

        2. This! As far as I’m concerned, the advertised price should be the price you pay… period! It seemed like in England and I think France, the shelf price was the register price. On the train, snacks weee extra.

        3. It’s not false advertising. You can fly for $58, and they VERY clear about charging more for a carry-on, checked bags, choosing you seat, and early boarding. There’s no tricks involved.

          If you don’t need those things, you can show up with your small personal item, fly, and be fine.

    3. I forget if it is Spirit or Frontier, but one of them does a Veteran appreciation program where a wide range of their nickel and dime costs are waived.
      I have indeed gotten quite a few $58-100 round trip tickets from whichever of those does that.

  19. winter in Florida is kind of the sweet spot. too late in the summer and you get into Hurricane season. too early and you get rain for a couple hours or maybe just an hour followed by baking sun, or basically a hot steam bath with lots of bugs.

    I loathe LA anymore simply because while the rest of the world has suddenly got a lot of terrible drivers, LA has stepped it up to whole new levels of self-centered bad driving. and the ocean s cold unless you go to San Diego.

  20. I took that same cheap flight from Chicago to Tampa last year at this time for the IndyCar Grand Prix of St. Petersburg. Tampa/St. Pete is spectacular, what a great place to escape the cold Midwest for a few days!

  21. I try not to do the pre-‘arse-crack-of-dawn’ flights any more. Some flights have been soo early that I’ve had to wait for the TSA to open up (they only allowed air crew and airport employees through before 15 minutes till first boarding time of the day). The price simply isn’t worth getting up at 1:30 or 2:00 AM. I can say “Been there and dun dat.” and moved on to later scheduled flight times.

    I’ve flown mostly SWA and even early morning, they are usually full flights. I used to see many more mostly empty flights back in the 90’s and 00’s. Unfortunately, they little commuter planes that you really needed the space on, were always packed, all the time.

    1. I like to get the earliest possible flight, but it’s not about the price.

      Airports are like computers: they work best immediately after a reboot. When the airport opens for the day, that is its reboot. As the day goes by, there will be small delays here and there; the small delays add up and can become large delays – e.g. this flight didn’t leave the gate so this other flight can’t get to the gate, repeat, repeat. Then, if you have a flight that is supposed to leave at 7pm it may not take off until 9pm or 10pm – or maybe not at all, then you’re stuck overnight.

      Getting up at 0300 is a PITA but IMO less annoying than being delayed significantly.

      1. Exactly! It’s just like booking an appointment somewhere. If you do it first thing, you miss the 10 minute late arrivals or simply appointments running over schedule.

  22. FL hints:
    – Don’t go to Miami. Go to the Everglades instead. Kayak / platform camp if you have time.
    – Do drive the overseas to Key West. Stay a few days, visit the art galleries and local drinking establishments, check out some of the other keys and see the sunset. Scuba or snorkel if you can, because some of the best scenery is underwater.
    – If beaches are your thing, the west coast and panhandle has the best sand and calmest water, the east coast has more surf. And while most people flock to the well-known beaches there are still some relatively unspoiled / not-yet-overpopulated beaches in the state. When you find them, don’t tell anybody.

    1. I agree with most of what you say except the Miami part. I wouldn’t live there or anything, but it’s definitely worth a visit to see the “South Beach” spectacle of the pretty model types and the fancy people/cars. It’s a definitely unique energy like Vegas, but for way different reasons.

      As far as the rest of it, you are 100% correct that the Gulf side is far better to explore, even though Hurricane Ian did quite the number to south of Tampa.

      Mercedes, I could almost guarantee that you’d really like Key West. It’s so much fun. Also, there are plenty of places along the way that have airboat tours that go inland to see wild gators and all the other things that can kill a human, lol. Those little day cruises are amazing to do firsthand.

      Florida gets a lot of shit, but it’s mostly a pretty awesome place to live/visit.

  23. “I’ve always wanted to drive on Florida’s Overseas Highway and the Seven Mile Bridge”

    This had always been a bucketlist item for me too and when I finally got to do it about 10 years ago there was a wreck on the bridge so we all put our cars in park, turned off the engines, and got out to look over the edge at the fish and sharks swimming around below the bridge. Anyways, as I’m getting out of my car I guess the guy behind me saw my TEXAS license plates because I hear someone shouting, “DALLAS SUCKS!!!” I’m from Houston so of course I just shrug and shout back, “I AGREE!!!” Apparently the Dallas sportsball team had treated the Miami sportsball team unkindly the night before or something.

    Btw, are we getting photos in the comments eventually? I’ve got a pic of us all out of our cars on that bridge.

Leave a Reply