Which flight would you go with?

Are you saying the layover on the Rome to London leg is less than Copenhagen’s 50 minutes?? 50 minutes is tight, if anything I’d want a slightly longer layover not a shorter one. I’m also imagining Copenhagen is a much smaller airport than Heathrow, and would be easier to make a connection. This is critical, you can’t miss the international leg.

This all sounds over complicated too. Are you piecing these flights together or are they a package? Are all legs on the same airline? If so, they are aware that passengers are making connections and will do their best to make it happen. Separate airlines have zero obligation to do so.

Separately, you really ought to plan on staying a night in Chicago on your return. A five hour drive after a long international flight(s) (immigration can take a long time too) feels like a disaster in the making. You don’t know how you’re going to feel. Be safe.

Lastly, you mentioned exchanging currency. Don’t exchange currency, the rates are exorbitant and most places are basically a scam. Taking euros out of an actual bank atm gets you the best exchange rates with minimal fees. Bring some cash if you want for emergencies, but don’t use it. Also, if anyone asks if you want to pay “with dollars or euros” always choose euros.

I'd go with the first option, Copenhagen. It is a great airport for transfer, not as large and hectic as the mega hubs so everything is close. Your arrival and departure gate will most likely not be more than a 5-10 minute walk from each other. At most. 50 minutes is plenty of time, I've done a non-Schengen to Schengen transfer in 15 minutes in Copenhagen. And I assume this is with SAS, they are not as big as British Airways or Lufthansa but is in general a good airline.

I would go with SAS out of O'Hare I've never had a problem; good quality for the price.

Re the rewards and points- SAS is a member of Star Alliance, so you should be able to credit those points to a United, making them more useful. Same with BA- credit to American for more useful point earning.

Separately, you really ought to plan on staying a night in Chicago on your return. A five hour drive after a long international flight(s) (immigration can take a long time too) feels like a disaster in the making. You don’t know how you’re going to feel. Be safe.

I agree with this comment. Have you done it before? The westbound flight is less tiring than the eastbound red-eye flight, but still, 2 hours is the most I can manage - and even then, I had a close call once leaving Boston in heavy traffic after the flight from Paris.

Perhaps not helpful, but neither of these options is great. If I had to choose one, I'd go with the British Airways flights and fly in and out of Rome. A 50-minute connection is always a gamble, in my opinion. I agree with those who are warning you away from driving 5 hours when you arrive in Chicago. That sounds exhausting. Naples is quick and easy to get to via train from Rome, by the way.

Thanks for all the replies. They've given me a lot to think about. I did want to address a few of the questions and concerns.

Just to clarify- the 50 minutes layover in Copenhagen is on the way back to the States. The "shorter" London stopover that I mentioned was on the outgoing flight to Rome. Which is why it gets me to Rome a little bit earlier. No, these flights are not piecemeal. Each option are both with their respective individual airline the whole way through. The 3-way flight would be booked as a Multi-City ticket, but it is still considered one booking.

As far as currency, I wasn't necessarily being literal. For the purposes of the post, I more or less meant "get money." Whether that is a currency exchange or an ATM. More than likely I will go the ATM route. I need to check with my bank to see what their international rates are. My only thing with ATMs is that in my experience, they only give big bills. This happened when I arrived in Scotland a few years ago. The train into the city, I don't remember how much it was, but it was a smaller amount, and of course they don't make change. There's no ticket kiosk either. You have to pay at a machine. So...I went to a little shop at the airport and bought a couple of little things- coke and candy maybe- in order to get smaller change to use. Well...so then, I missed the train I could have been on and had to wait for the next one...it was just a whole thing. That's my only issue with an ATM.

Yes, the Copenhagen option is SAS, as some have guessed. I am not super familiar with this airline, but it seems like it is really up and coming. I like what I have read and seen of it. I'm not particularly snobbish when it comes to airlines. I don't typically fly United, so that's not as much a draw for me. I don't have a major affinity for British Airways, other than I know it's a pretty ubiquitous international airline. And, I can see myself flying to the UK more commonly than any other overseas locations.

As far as returning to the States, yes I have done a late-ish Westbound flight before. It's one of those things where....I just want to make it out of Chicago. But, then, I think.....just another hour, just another hour. Then, I'm halfway, and then at that point, it's like....I might as well just drive the whole way, ya know? Previously, I drove to my uncle's which is about 3 hours. I was thankful to have a stopping point. I do have a friend about halfway or my uncle's as I mentioned. So....once I get closer, I might reach out and see about staying over with either of them.

The secret to avoiding large bills at ATMs is to withdraw 40 euros or 40 UK pounds. The worst you can end up with is two 20s. That is only sensible if the ATM doesn't charge a per-transaction withdrawal fee and your financial institution doesn't assess a flat-rate fee, either.

If you don't like the fees being charged by your bank and/or your credit card companies, you have time to open additional accounts that are friendlier to international travelers.

CapitalOne's 360 accounts can be set up easily online and have no international fees on their ATM cards. You can set up a Charles Schwab account and get a no-fee ATM card; you don't have to make any investments through Schwab. Some credit unions offer no-fee ATM cards.

At least some Capital One credit cards have no international feels, as do some airline mileage cards, but with the airline cards I'm not 100% sure you can avoid annual fees--though I think you can in some cases.

Fifty minutes in Copenhagen is tight. Its not just changing gates. Since it is your last stop in Schengen, you will have to go through exit immigration and get your passport stamped.

Any delay in your fight from Naples, or crowds at passport control, and you could miss your flight to the U.S. Copenhagen is not that small of an airport. I wouldn't feel comfortable with that short of a layover.

With the British Airways flight, both flights would be in one terminal, you would do your exit immigration in Rome, and the only thing you'd have to deal with in London is security.

Just how big of a risk taker are you?

On your return to the US, 50 minutes in Copenhagen is not enough time to land, go through immigration and then board. The airport isn’t small.

Just to clarify- the 50 minutes layover in Copenhagen is on the way
back to the States. The "shorter" London stopover that I mentioned was
on the outgoing flight to Rome.

50 minutes in Copenhagen is not something I would worry about. It is a pretty small airport compared to Heathrow, Frankfurt, Schiphol and the other mega hubs. I would not want it much shorter though. How long are the other layovers? All in all, Copenhagen airport is pretty efficient for connections in my opinion. You would need to go through a passport check, but there is no need for another security check.

Yes, the Copenhagen option is SAS, as some have guessed. I am not
super familiar with this airline, but it seems like it is really up
and coming.

SAS was founded in 1946 through the merger of three airlined, so it is almost 30 years older than British Airways. And if you count the history of the three airlines that were merged, SAS is one of the oldest still operating airlines in the world. https://en.wikipedia.org/wiki/Scandinavian_Airlines

I like what I have read and seen of it. I'm not particularly snobbish
when it comes to airlines.

How much are you planning to spend on the flight? A transatlantic flight in economy is something you endure rather than enjoy, no matter what airline. But if you're planning to spend a bit more, SAS offers a very nice business class https://youtu.be/k9fGmwPUUQ4?t=360 And their A350s are pretty nice.

On your return to the US, 50 minutes in Copenhagen is not enough time
to land, go through immigration and then board.

It is enough time in my opinion.

Of course, I know that SAS has been around for a while and is well established. I guess what I meant is, I have read that SAS has really ramped up in 2023, and is adding more routes and more flights....so it seems like they are ever-growing, into more of a mainstream option.

The Copenhagen option certainly is not ideal. I'm not super worried about the 50 minutes, in the sense that from what I can tell, both will arrive and depart in the same Terminal. But, it's all the extra unknowns.....the delay possibilities, the passport and security issues.

Speaking of passport and security...

If I purchase something in duty-free in Naples, something like a bottle of wine....will that cause any issues in Copenhagen? Like...they won't make me throw it out for being too large, right?

It doesn’t matter really that your flights in CPH are within the same terminal. You will be herded in to immigration area to board your US flight and there will likely be a wait.

Information for US travellers
On flights from Copenhagen Airport to the US, there is an additional security check at the gate. Ensure all mobile/electronic devices have enough battery power to be turned on at security if requested.
https://www.cph.dk/en/practical/luggage/rules-for-carry-on-luggage

.

Transfer passengers arriving from outside of EU

If you arrive at Copenhagen Airport from a country outside of EU and have to continue travelling by airplane, you will have to go through the security check. Please note that the same limitations apply to liquids as any other departure from the airport.
Passengers in transit at the airport who have purchased liquids over 100 ml at either another airport or aboard an aircraft, must ensure that the liquids are sealed with the STEB (Security Tamper Evident Bag) and the receipt for the liquids visible in the bag.
https://www.cph.dk/en/practical/luggage/liquid-rules

"Maybe', a wine bottle could get through.??

Hopefully someone who has gone through the airport can provide a 1st hand account.

You could procrastinate long enough that one or the other flight price changes enough for you to have to go with what is left. The your decision is made.

If I purchase something in duty-free in Naples, something like a bottle of wine....will that cause any issues in Copenhagen? Like...they won't make me throw it out for being too large, right?

Careful with this part. Not sure how it will be in Copenhagen, but I did a similar thing with a nice (and not cheap) bottle of duty-free scotch purchased at Heathrow. Our final destination was Seattle, connecting through Vancouver, BC, where (and this is a key piece that wasn't ever mentioned until we landed) we had to clear customs/immigration before boarding our connecting flight.

It was at that point (still on the secure side, as we had just gotten of a transatlantic flight), that the perfectly safe bottle that I carried onto to the plane in Heathrow suddenly became something I couldn't carry-on to the next flight, because it was over 3 oz. Now I had to decide to try and check it (and possibly miss my tight connection), or leave it on the counter.

Left it there, giving the local officials there yet another prize from an unsuspecting (and unsuspicious) traveler.

(Side note: Probably not the first person that's happened to, so I bet the collection the Vancouver team's built over the years is impressive! ; )

I guess what I meant is, I have read that SAS has really ramped up in
2023, and is adding more routes and more flights....so it seems like
they are ever-growing, into more of a mainstream option.

They have, which isn't really too surprising after a few pandemic years. Also with the russian airspace closed they need to find new uses for the planes that used to fly to Japan and China.

But, it's all the extra unknowns.....the delay possibilities, the
passport and security issues.

The change involves a walk from one gate to another, a passport check and the extra security check for departures to the US. The Chicago flight departs 15:55 which is hardly rush hour at the airport so there will probably not be any large passport queues. And should you miss it, they have other options, like rerouting you via Stockholm or New York.

You could procrastinate long enough that one or the other flight price changes enough for you to have to go with what is left. The your decision is made.

You are so right. I keep waffling. Keep going back and forth. Every time I think I have it decided which way I am going, I change my mind. I just need to make a decision and stick with it.

The change involves a walk from one gate to another, a passport check and the extra security check for departures to the US. The Chicago flight departs 15:55 which is hardly rush hour at the airport so there will probably not be any large passport queues. And should you miss it, they have other options, like rerouting you via Stockholm or New York.

This is definitely somewhat a comfort. And truth be known....I am flying back on a Saturday, so there is a little bit of a buffer there. Ideally I'd like to get back Saturday, that way I have Sunday to relax and unwind, unpack, sleep in my own bed....all that good stuff. But, if worse comes to worse, and I AM stuck there overnight, I suppose there are worse things than having extra time to explore a new location.

Careful with this part. Not sure how it will be in Copenhagen, but I did a similar thing with a nice (and not cheap) bottle of duty-free scotch purchased at Heathrow. Our final destination was Seattle, connecting through Vancouver, BC, where (and this is a key piece that wasn't ever mentioned until we landed) we had to clear customs/immigration before boarding our connecting flight.

It was at that point (still on the secure side, as we had just gotten of a transatlantic flight), that the perfectly safe bottle that I carried onto to the plane in Heathrow suddenly became something I couldn't carry-on to the next flight, because it was over 3 oz. Now I had to decide to try and check it (and possibly miss my tight connection), or leave it on the counter.

Left it there, giving the local officials there yet another prize from an unsuspecting (and unsuspicious) traveler.

(Side note: Probably not the first person that's happened to, so I bet the collection the Vancouver team's built over the years is impressive! ; )>

Oh goodness! What a story.

I went through a very similar situation. I bought some Guinness from the storehouse in Dublin for my brother in law. And I had a flight from Dublin to Edinburgh. I don't know what I was thinking, I guess I wasn't thinking. When I arrived in Dublin, I discussed my plans to travel onto the UK with the immigration agent. And, I dunno...I guess in my mind, it was a short domestic flight, and I can't explain why I thought there would be no security....like I said...just not thinking.

But, yeah, I ended up leaving $50 worth of Guinness there in Dublin.

I am flying back on a Saturday, so there is a little bit of a buffer
there.

Saturday is typically the slowest travel day, so that is also a good thing.

And, should you miss it they have a flight to New York a few hours later, and a flight from Stockholm to Chicago that departs sunday morning.

Welp, thanks everybody for this long saga.

I booked my flights this evening, so....I suppose that's that.

I booked my flights this evening, so....I suppose that's that

Not quite.... you going to leave us all wondering what you chose?

Haha, sorry didn't mean to cause any suspense.

I ended up going with the SAS flight through Copenhagen. I am not thrilled with getting to Rome late, but that's okay.

It helped to view things with some perspective. The fact is SAS is selling it as a flight. As a flight from Naples to Chicago, with a connection in Copenhagen. If they didn't think there was at least a reasonable probability that the first flight would arrive on time, and passengers would be able to board the second flight within that 50 minutes....they wouldn't sell it as a flight.

I read up on some of the EU rules on delays and compensation, and while I hope I don't get delayed, I do feel like I will be taken care of either way. Either they will get me on another flight ASAP, or I will be stuck there overnight, and I would be compensated a fair amount.

I do have a buffer, so if worse comes to worse, I will get in on Sunday, and have a little bit less time to veg before heading back to work. There are certainly worse things.

Good luck! I really hope you report back how it went after the trip!