Sometimes when you position to catch an international flight, you end up with a longer layover than a typical connection. This may be advisable because you don’t want to miss the international premium class redemption that you scored with your valuable points.

Other times, you may intentionally (or be forced to) book a longer layover in the middle of an award redemption because either the only flight available on one of the legs is earlier or later than you would have liked or because you are taking the opportunity to add a quick visit to an extra city along the way.

In 2019, I decided to meet our younger daughter in Israel after she finished a summer program so that she and I could spend a few days with relatives that live there who we don’t get to see very often. As I was traveling solo, I had some flexibility on how to get there using points and miles. Israel can be a tough destination to find business class award tickets as there aren’t that many nonstop flights from the US (even during relatively peaceful times).

I wanted to avoid transiting through London or Paris as London has high business class fees added to every ticket and Paris can often be difficult to connect through in the summer with the added complication of potential strikes as well. I managed to find an itinerary using 70k American Airlines miles from Atlanta to Tel Aviv via Charlotte and Madrid.

The connection in Charlotte was short and I almost missed it when our flight from Atlanta was delayed, but I made it on the flight to Madrid on an American Airlines A330 (US Air legacy plane that was retired the next year during Covid). My connection in Madrid was from about 8am until 4pm, and I selected this itinerary purposely as I had never been to Madrid before. I stored my bags at a luggage storage place in the airport for a few Euros and took the airport bus into town. From the bus stop, I walked around the main tourist area for a few hours, stopped by the Mercado San Miguel and ate some ham and cheese in the Plaza Mayor. Around 1pm, I took the airport bus back the other way, grabbed my bags and went to the Iberia lounge where I showered and ate some more ham and cheese. Then I took an evening Iberia A330 business class flight to Tel Aviv where my cousin picked me up around 8pm local time.

All three flights were included in my itinerary and one of the better aspects of this particular itinerary was the lay-flat business class seats on the leg from Madrid to Tel Aviv. Any American Airlines award itinerary through London would have included the higher fees and a worse product from London to Tel Aviv on British Airways in Club Europe (likely a narrow-body aircraft with economy seats and an open middle seat). If my wife was with me, I likely would have just booked a one-stop itinerary without a long layover, but since I was by myself, I wanted a bit of an adventure along the way.

For my upcoming YOLO solo trip next week, I have set up a long layover in Chicago because I don’t want to miss my Emirates Gamechanger flight that evening. I currently have two different award flights booked to Chicago from Atlanta, an midday flight on American and an early afternoon flight on Delta. I will likely take the American flight assuming it’s on time and just cancel the Delta flight (as the miles will be reinstated at no cost).

So, what am I doing for eight hours in Chicago? Well, first of all, it’s more like 5-6 hours total as I would want to check-in with Emirates a couple of hours before the flight and board early to enjoy the Gamechanger cabin as soon as possible. My plan will depend quite a bit on the weather. If the weather is bad (either raining or 90+ degrees), I will likely just visit the American Airlines Flagship lounge, which my current British Airways Gold status gives me access to, before heading over to Terminal 5 when Emirates check-in opens around 4:30pm.

If the weather is pleasant, I have another plan. I have a rental car reserved for the afternoon so upon landing from Atlanta, I will head over to the rental car center and drive to a nearby nature preserve with a long hiking trail. I will hike for a couple of hours before heading back to the airport. My Emirates First Class ticket gives me access to the new LOT Polish Lounge in Terminal 5 which has showers available, so I can shower and change before my evening flight. Getting out and getting some exercise is a good idea before I spend over 20 hours on planes eating caviar and drinking champagne. So far the forecast looks pretty good (mid-80’s) so I plan to get out of the airport and get some exercise. I’ll have a full review of my trip, including my Chicago layover, when I get back.

If you find yourself with a long layover, think about getting out of the airport. But before you start planning your next long layover adventure, here are some things to watch out for because even the savviest travelers can slip up.

1. Don’t skip the visa check

Some countries require a visa or entry clearance even if you’re just getting out of the airport for a few hours. Double-check before you travel.

2. Factor in travel time to and from the airport

An “8-hour layover” sounds great—until you realize the city’s rush hour or the airport shuttle takes forever. Plan your timing wisely.

3. Pack light and smart

If you want to explore, make sure your carry-on is easy to handle. If you can find baggage storage at the airport, bring a small day bag with you to carry your essentials while you’re out and about.

4. Don’t rely only on lounges

If you’re not flying in international business or first class or don’t have airline lounge access via status, Priority Pass lounges can fill up fast, especially at busy airports. Have a backup plan, whether that’s just a an airport restaurant, or even a paid lounge with showers when you return from your trip into town.

5. You may need some cash

You can get by with a credit card in most countries, but in some places if you’re venturing into the city, you might need cash for buses, trains, meals, or a quick museum visit.

Keeping these things in mind, think outside the box when you have a long layover. Don’t plan to spend the whole time in the lounge or the airport if you can find a way to have a different experience.

If you have questions about this post, let me know in the comments or send me an email at emptynestermiles@gmail.com. If you are thinking about opening a new credit card, please use one of my links.