Seeking tips flight from Chicago to Sorrento

Your best options are: 1) a flight to Naples, probably with one change of plane at an airport along the way, and then the direct bus from the airport to Sorrento, or 2) a direct flight to Rome, Leonardo Express train to Roma Termini and high-speed train to Napoli Centrale where you could either arrange a private transfer to Sorrento, transfer to the ferry dock and take a ferry, take the nice but infrequent Campania Express train or take the frequent but not so nice Circumvesuviana train. Based on your criteria, if flying via Rome I would splurge on the private transfer (ballpark 100 euro, although you may be able to find a reliable transfer service for a bit less). If flying via Naples, the direct bus is perfectly fine.

We paid a driver 120€ From Sorrento to Naples airport two years ago. If you can get a direct flight to Naples, I would book it. I have been getting lots of promotions from Air Italy lately. You may have to fly to Rome though.

You keep referencing "safe." All the ways are safe but do you have a particular concern about safety? I doubt if there is a direct flight from Chicago to Naples. You can look but Naples is a pretty small airport. Any of the method works. It is just a matter of price and time. For us we would book a flight into Europe somewhere, perhaps Rome or Milan, and change to a flight to Naples and bus from there. Or take a bus to the Naples train station and train from there. The Circumvesuvianna train takes lot of heat but we had ridden it four times with absolutely no problems. Just take the usual precautions you would take in riding any train in Italy.

PS -- time of year for your trip????

Fly Chicago to Rome direct.
Take the train Rome to Naples
Change trains in Naples to take the Circumvesuviana to Sorrento.

This is definitely safer than going from your home to O'hare in Chicago with all the crime and shooting that goes on here.

You got choices! Flying directly into Naples is one good plan. (Did someone say 120 euro for a car to Sorrento? I'm only paying 80 euro tomorrow!). You have to check schedules, but from Naples why not start your vacation on the water? The ferry service from Naples to Sorrento may not be convenient for your schedule, but if you can make it work I highly recommend it! Great scenery, comfortable traveling conditions and fresh air. It will take some of the stress from the long flight away.
I fly into Rome and take the Freccia train to Naples. It's easy, comfortable and, for me, a direct flight. I fly from Philadelphia and my flight arrives early in the morning. The last thing I want to deal with, usually, is changing planes, worrying about luggage and schedules. Even the Freccia reminds me that I'm on vacation!
Whatever - enjoy your trip! Sorrento is a great place. I veg out, eat and shop there a week every year!

Please tell us more about your total trip. Is it only to Sorrento? United Airlines has high-season flights from the NYC area direct to Naples-probably not every day. You might want to connect to one of those. Referring to an aspect of "safety" you may not have considered, there used to be an obscure, tiny airline that offered one or two flights a week from JFK (?) to Naples, but the few reviews I could find were poor or mentioned sudden cancellations.

You can use the Search box here to read many discussions of bus, train, and ferry connections (and intermediate taxis in some cases) between Naples airport and Sorrento. Enter search terms like "Naples Airport Sorrento" or similar. Then click the Travelers Forum link. The traveler's budget, physical ability, luggage size, time of year, and ARRIVAL TIME in Naples all factor in to this. (I mean, when we came from London after the Chelsea Flower Show, we arrived so late that we had to spend the first night in Naples (by pre-arrangement, which was fine with us.)

Sorrento hotels book up six to nine months in advance. When are you hoping to go?

We always prefer to fly directly to Europe whenever possible. We figure at least we are then in Europe if we miss a connecting flight or lose our luggage. A flight from Chicago to JFK- has its risks. If you miss the flight to Europe from there you are likely stuck til next day for next flight out. (I have flown out of Philly to Europe when we waited as long as they could for all the passengers coming from BWI- that were booked on our flight. It was in the summer and thunderstorms were the culprit- all those folks got stuck in Philly.).
We drive to Philly to avoid that possible problem.

So, that said if you can get a direct flight from Chicago to Rome I'd book that. Then trains to Sorrento via Naples. Or book a private transfer from Naples station to Sorrento. Or stay in Rome for a few days if you'd like.
For flight home you will want to be in your departure city the night before- whether that is Naples or Rome- so keep that in mind.

We loved Sorrento but it does mean you've got to figure out the transportation logistics. There are lots of options.

If you tell us more about your overall trip we can be more specific in our advice.

First off, there are no direct flights Chicago to Naples. And I agree with Christine in that my first flight needs to get me to Europe. That being said, I am partial to Lufthansa and would fly from O'Hare to either Frankfurt or Munich, then to Naples from there.

Maybe I shouldn't assume, but if Sorrento is your first destination, you won't want to take a commuter train from Naples to Sorrento, even if the Circumvesuviana is cheap and easy to take. There will be time for the CV if you travel on a daytrip from Sorrento to Pompei or Naples.

Because you'll probably be jetlagged, contact your hotelier in Sorrento and see if they can make arrangements to pick you up at Napoli Capodichino airport and drive you directly to your hotel. You won't want to walk anymore, believe me. Yes, it is pricey at anywhere between 80 to 120 Euro--they charge it because they can.

Something cheaper--if it fits into your schedule--is the Curreri Viaggi bus. Check it out--https://www.curreriviaggi.it/

Wanted to add this since OP asked about the “most safe and efficient” way to fly.

The safest and most efficient- although not necessarily least expensive -way to fly to Europe is to be sure you book your flights directly with the actual airlines and that all connecting flights are on same ticket. Your luggage- if you are checking bags- will be checked thru to your final destination when you leave Chicago.
IOW-don’t be tempted to grab that “really good deal” on expedia or kayak or wherever. Those “deals” usually mean you are flying on diff airlines with iffy connection times or long layovers
If anything goes wrong - you miss a connection, lose your luggage, etc- expedia or kayak will be of no help to you.

I was never a fan of United/Lufthansa as Jay is until our trip last month. We left Newark about 75 min late- so I was worried the whole night about missing our connection in Frankfurt to Rome. Yet I did know that United/Lufthansa would take care of us. We arrived in Frankfurt about 60 min late so we had less than 40 min to make our connecting flight on Lufthansa to Rome. We made it just barely- I figured our luggage would not. We were shocked when our bags were the first off the belt in Rome- so kudos to Lufthansa! (Although that weird sandwich they served us was well…rather disgusting)

We used this company for 2 transfers while in Sorrento/Amalfi and were very pleased, we thought it was money well spent. Their rate from Naples to Sorrento is 95€
https://www.topexcursionsorrento.com/en/transfers