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August 2021 travel plans, taking to the friendly skies

Ben and I are at a beach in Florida.

If you are on my email list (you can sign up below if you are not), you may remember that I am planning a trip to Florida to visit my friend, Ben, or, as he might say, “acquaintance.”

All of my travels this year have been for or with family. I love my family, but I could use a break from them, and I am sure they could use a break from me.

Plus, I want to get out of the midwest for a little while.

The last time I saw Ben was when he returned to Wisconsin in 2019, so I guess it was my turn to visit him.

My last time out of the Midwest was a quick trip to DC and back home in December 2020.

In my true trip-planning style, I started working on two trips simultaneously. The next adventure is a train trip to Pittsburgh, Philadelphia, and Washington, DC. That will be in October.

So, I found a great deal.

I saw an ad for Spirit Airlines offering $43 tickets to Orlando from Chicago in July. It seemed like a decent deal.


Since I could pack very light for this getaway, I figured I could skirt the carry-on bag fee (about $44), but this means I need to pack my stuff within their free personal item bag policy.

I thought the experience could be worth the trip, although I would have to compromise.

If you have not looked into discount airlines, those cheap tickets often get expensive fast. They use the term ala cart booking, meaning you only pay for what you use. While this sounds great, I often find those deals quickly cost more than the non-discount airline.

Since I could pack light, I could keep the cost at that great price, but I discovered a problem. I thought Orlando was closer to St Petersburg, but Ben quickly corrected me and told me to try again. Geez, some friends are too needy. haha

I started running into problems.

The other problem with discount airlines is that some only fly on certain days and have limited flights, so I had logistical issues with booking. I almost gave up because of this frustration.

Before giving up, I looked to Southwest Airlines and found they had $59 tickets each way! I talked with Ben and found flights that work well for all parties involved. The trip is back on!

Why I am glad this is how things worked out

I have flown with Southwest before, and I like the Southwest experience. Plus, I built up points with them since my first flight in 2016.

Southwest Boarding pass
You get your Southwest boarding pass and your group and position information.

I love and hate Southwest’s boarding procedure. They do not have assigned seats if you have not experienced them before.

The chances of getting an aisle or window seat are good if you have an A or B boarding number. But if you have group C, they have a joke; group C is the center seat group. But seriously, it is true.

When you board the plane, you can pick any non-occupied seat.

Twenty-four hours before your flight, you check in for the flight. After you check in, Southwest gives you your boarding position.

If you want to make sure you get a better seat, for a fee, you can go for the early bird option that checks you in early, so you usually get the A or early B group.

While I plan to pack light, Southwest allows a carry-on and a personal item as part of my ticket. If I wanted to get the same bag on a discount airline, it would cost close to $38-$40 just for my backpack!

I was excited with more convenient times, legroom, carrying my bag for free, not paying for my seat, free onboard snacks and drink, and more for $59.

My options

I am fortunate to live in an area where I can access many ground and air transportation options.

Going through the TSA

I live within a 30-45 minute drive to the Milwaukee Mitchel Airport, three Amtrak stations, plus a few Metra stations. And between trains and busses, I can get to both of Chicago’s Airports quickly without asking someone to drive me there.

From the Sturtevant Depot, I can take the train directly to the Milwaukee Mitchel Airport or downtown Milwaukee to pick up Greyhound and other bus lines or to Chicago to catch the CTA. So, it is easy and not expensive for me to fly out of the two Chicago airports with those options.

If I wanted to be adventurous, I could take a train or bus from Chicago to airports like South Bend, IN, and Bloomington-Normal, IL.

Why I booked the way I did

Milwaukee’s prices were too high for what I wanted to spend—even factoring in the transportation cost to Chicago. I tried to book a round trip ticket instead of two one-way because sometimes it’s cheaper. That technique did not work for this trip.

Instead, I discovered that leaving one airport and returning to the other was cheaper. Later you’ll find out how it will be easier for me. So, I came up with flying out of O’Hare to Tampa and, coming back, flying into Midway.

Going to Chicago

My flight out of Chicago’s O’Hare Airport is at 7:45 pm, and I picked a later flight because of cost and work. The night’s last flight was the cheapest, so I would not have to rush to the airport.

Metra Locomotive
A Metra train is waiting for passengers at Chicago Union Station.

The cheapest way to get to Chicago is Metra out of Fox Lake. The train takes up some time because the ride is a little over an hour and a half. After leaving Union Station, I transfer to the CTA, about an hour’s ride north.

I have the time to “waste,” and I enjoy the journey to the airport.

Amtrak works better for my dad, who is dropping me off. Amtrak is more comfortable and saves me about a half-hour, but it costs more. I would still need to transfer to the Blue Line CTA like Metra.

I also looked at taking Amtrak to Milwaukee and then transferring to a bus to Chicago. But then I found another option; it had good timing, was more convenient, and was reasonably priced.

I came up with taking the Coach USA airport shuttle from the Sturtevant (Racine) to O’Hare for $29. It works for me, and my dad can quickly drop me off. The most significant advantage is that the bus takes me to the terminal I need! It costs more than Amtrak and CTA combined, but the convenience is worth the extra money.

Coming Home

Right now, I will wait till I am at the Tampa Airport, waiting to go home, to decide. I would consider Coach USA, but they do not go to Midway. More than likely, I will take Metra to Fox Lake or Amtrak to Sturtevant. That is the advantage of having a few transportation choices.

How much does the trip cost?

As of now, the trip cost breaks down to this:

  • $28 for the bus to O’Hare Airport
  • $59 for the flight from O]Hare to Tampa
  • $59 for the flight from Tampa to Midway
  • $2.50 CTA from Midway to Chicago Union Station
  • $9.50 – $24 for the train ride back to Fox Lake or Sturtevant

So I am looking at around $158 – $172.50 depending on how I get home from Chicago, which is just for transportation. I used a $9 credit towards one of the flights, which slightly lowered the cost.

Wait a minute!

So, for fun, I checked the price of my flights and noticed that the price went down by $10! I was able to rebook both flights at the same time. So, I received a $20 credit for future flights between the two flights.

So now the cost is around $138 to $152.50!


A few things about this trip could cause last-minute changes of plans, like hurricanes or if the pandemic worsens in the next few days.

SWA Sunrise
Sunrise from the window of a Southwest 737-700 flying over Iowa

My plans for the trip are to hang out with Ben, and I think he has a pool and boat.

Besides that, I plan on working on new articles. We talked about going to the Tampa Zoo and possibly other places.

With things being the way they are, I don’t feel like going to bustling indoor places. I did buy some new facemasks, and I did get my vaccines. Is it okay to wear an Amtrak face mask on the plane?

Thanks for learning about my trip planning, and I will let you know how this trip went!

If you are interested in following along, you can join the email list to receive weekly updates, travel updates, etc. Also, if you get something from Travels with Kev, consider being a supporter at a one-time level or getting a membership.

Safe travels!



Kev has been traveling with Amtrak since 2012, celebrating his tenth year this year. Over those years, he has been on over 700 trains covering over 200,000 miles of rail. Kev enjoys helping others achieve their travel dreams by assisting them with support and information. Kev enjoys making music as an organist.

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