Note: I wrote these remembrance posts a few weeks ago, and I was feeling nostalgic and looking forward to my next trip to Istanbul, which looked to possibly be in 2027. Unfortunately, with the news that Recep Tayyip Erdoğan’s authoritarian arrests and intimidation of members of the LGBT community, I can no longer plan to visit or suggest anyone else visit. Back in 2018, we had discussed that this is where things were heading, but after eight years, I was hoping Istanbul, at least, would be spared. These writings were from happier times for the city.
Since July 9th, I have been home in Chicago, it’s been a long three weeks, but I am currently on a flight to Fort Lauderdale for a work conference. It was nice to be home, but after being on the road for almost two months straight, it also felt a little stagnant to be in the same place for a while. I also find it easier to blog when I am in transit somewhere, which is why the blog took a pause, too.
In the previous post, I talked about some of my travel history, and how I really couldn’t afford big trips, or at least, I wasn’t willing to put everything on a credit card to do those trips (I had credit card debt for other things to contend with), but I still got to travel a bit, mostly to surrounding states and longer road trips.
However, in late 2017/early 2018, I had made the decision that it was finally time to get to Europe. I had been dreaming of Prague since college, and while the plans were still furtive, I knew Prague would be on the list of places to go. While, even then, I knew I wanted more of a solo traveling experience than trying to find a group travel itinerary, I had somewhat settled on a package that would fly me into Vienna, and then take me via train to Budapest, Prague, and Berlin, which is an itinerary I finally followed back in May.
During the course of the aforementioned road trips, I had become friends, though my friend Ian, with Jerrad, who did a lot of international travel for work, and he was currently on an extended stay in Istanbul, Türkye, and while I have always been a history buff and interested in the Roman and Holy Roman Empires, the Ottoman Empire was an historical blind spot for me. While I wouldn’t say I was disinterested in Istanbul, I wouldn’t say it was in my Top 10 places at that time.
While money was not as much of a problem as it once had been, one thing that certainly helped me make the decision to fly to Istanbul instead of staying the whole time in Europe was the fact that I could stay with Jerrad in his flat along with his future husband, Burhan. I know, at that time, I was 43 years old and couch surfing, but again, my philosophy around travel has always been about the experience and not the accommodations, which turned out to be fantastic.
In early 2018, as we’ve established, I wasn’t a frequent air traveler, and when I did fly, I went Southwest, which was obviously not an option for international travel, and Jerrad suggested I look into Turkish Airlines. While I really do not recall much about my research process at that time, I absolutely knew that premium economy or business class was not in the budget. However, my window seat in economy came in at under $900 when I booked my flight in February 2018. I considered that a pretty good bargain for 12 hour, round trip flights, and with the money saved by staying with Jerrad, I settled on leaving on August 31st and returning on September 15th, making it the longest vacation I had ever taken in my life.
Istanbul was pretty much an unknown quantity to me, and I spent the rest of the time researching the city and what I wanted to do while I was there. I was certainly not as organized as I am now. I didn’t have WanderLog to plan everything out, and I also didn’t even remember to drop pins on Google Maps. Part of my process getting ready to write this post was to go back through my 1,000 pictures to recreate my stops and drop pins.
One thing I did plan was two, shorter trips from Istanbul. I booked flights on Pegasus airlines, a regional, low cost carrier to take Prague and Athens. Since I was able to keep Istanbul as a home base, I could leave the majority of my things there and just travel with my large travel backpack. It all worked out fairly well, but while I will probably not cover Prague again in a post, I will plan one to do one for Athens at some point in the future.
With all the travel logistics worked out, it then just became a matter of creating a list of what I wanted to see and do. Much as I still do, I watched a lot of travel videos on YouTube to get ideas and the lay of the land. Luckily, I was able to rely on Jerrad and Burhan for a lot of it, and while I didn’t pack in as much in a day as I would in future trips, I got to see a lot of Istanbul on my own.
I was still in Indianapolis at the time, and even though it is Indianapolis International Airport, there really were no truly international flights to Europe, and part of my cost savings plan was to not pay for a flight from Indianapolis to Chicago, which would have added at least $300 onto my total. I opted to use Amtrak to get to and from Chicago. At that time, Indiana paid for daily service, which made it easy and obnoxiously affordable.
Leading up to my departure, I started to have some severe gastrointestinal issues. It was very bad, almost to the point that I thought I may need to go to the hospital and cancel my trip. The last thing I wanted to do was to be caught in a metal tube for 12 hours with what was going on in my system, but while I still was not 100%, by the time departure day arrived, I felt like I could handle it.
For this trip, I had researched all the best ways to pack and not go over my weight limit. I took a larger suitcase, but since I knew I would be able to do laundry in Istanbul, along with the fact it was going to be hot, I was easily able to keep my bag underweight.
The train left Indianapolis at 6am, which got be into Chicago Union Station around 10am Chicago time. This left me with quite a bit of time to kill before needing to get to O’Hare. I made my way to the Roosevelt Collection shopping center, and I went to see Crazy Rich Asians, which is ironic because I think that has become an airplane movie staple for many.
After the movie, I made my way to the Blue line to take the train to O’Hare, which dropped me off right in the tunnel that was the nightmare scenario that happened the last time I flew out of O’Hare back in high school. Long story short, I had a connection to get back to Indy, but my flight was delayed, missed my connection, and I was put up in the Hilton connected to the airport by that very tunnel. I wake up for my early flight, and all a sudden the lights go out in the hotel and the tunnel, and I have to find my way in the dark to O’Hare. I was a senior in high school on my first flight by myself. Heady stuff!
Anyway, I get to O’Hare in Terminal 2, and I had to take the inter-terminal tram to Terminal 5. I had some time to kill (no lounge access for me then!), but I eventually make my way to my gate and see the gigantic Turkish Airlines plane. I had flown a 777 wide body to Seattle once, but most of my flights had been single aisle narrow bodied jets, and this one just seemed SO big.
Once we got boarded, I settled into my window seat. I wasn’t used to in-seat screens and entertainment, and while I did end up watching almost the entire Lord of the Rings trilogy on the way there, I was obsessed with the camera access to see what we were flying over. It is still one of my favorite features.
Even in steerage, the food on Turkish Airlines was very good, and luckily, I didn’t have any gastrointestinal issues for the duration of the flight. Indeed, I think my body goes into airplane mode when I fly, because I didn’t even need to get up to use the restroom at all.
We left Chicago on Friday, August 31st at 9:33 PM, and we arrived in Istanbul Atatürk at 4:20 PM on Saturday, September 1st, and after a much needed trip to the restroom, I made my way to through my first international border crossing. Other than being incredibly afraid of pissing off the border crossing official, it was pretty painless.
Ironically, Jerrad was arriving back in Istanbul from a trip, and I was able to meet him in the airport, which made navigating the taxi process a lot easier. After almost a year’s worth of planning, I was on my way into Istanbul to begin my first major travel adventure.
In Part 2, I’ll dig into all the sights that I got to see in this beautiful and historic city.




