Getting to Sicily and back

Do you also suggest coming one or two days early

Absolutely! The more the better.

Didn't do the research, but suspect there are Chicago to Rome flights that offer connection to Sicily. Depending on your choice of airline, there are likely one stop options through several other cities in Europe. Just a matter of balancing, price, flight times and connecting airport preference.

Happy travels

A couple days before the tour would be nice as would a couple days when it’s over.

When we flew to Sicily we had a layover in Munich. On the return the layover was in Frankfurt. I agree with joe32f that there are plenty of options to get to Sicily from other cities. It’s just which connection works for you.

Not taken a tour, but I traveled to Europe reasonably often for work, and you will want days on the front for sure, on the back end would be nice, you want to be 100% the first day of the tour.

Figure as well, the tour only hits a few highlights of the starting and ending (or any) city, so there will be plenty to see and do.

As for flights, see what connections you can get through your preferred airline and their partners. Getting back from Catania may be easier than getting to Palermo. One strategy that people use is to fly to Rome, spend a couple days, then fly to Palermo on a separate ticket. So you might look at an open jaw ticket Chicago to Rome, and then Catania to Chicago. You could also do round trip to Rome and arrange travel within Italy separately.

Go to Google Flights.

Select the Multi-City option.

First flight: ORD to Palermo

Second Flight: Catania to ORD

Put in the dates of travel and whether you want economy or business class. It will give you lots of flight options and the price. (We suggest booking directly with the airline.)

Definitely arrive at least two days ahead of time to fight any jet lag you may get.

hey hey johnaatkin
absolutely few days earlier, like joe32F says. jetlag is REAL and day of arrival in palermo will be "foggy" after a long flight.
check flight arrival since check-in is 3-4pm. if too early drop off bags until check-in, roam around, nothing planned, have dinner. get a good night's sleep. palermo will be busy and probably crowded but enjoy the town, street markets/vendors, sit at an outside cafe and people watch. get a good nights sleep, check-out usually 10-11am. meet your tour group and continue the fun.
after tour in catania, spend the night, check the times of flight back to ORD, no early morning (6am to 10am) afternoon much better.
look for multi-city flights which suits you) ORD to PMO CTA to ORD. hope all works out for you with others here to offer any other opinions. enjoy and have fun
aloha

The Best of Sicily is a wonderful tour, but really doesn’t spend enough time in Palermo. So, yes - Spend a day or two extra there!

I flew round trip, MInneapolis to Rome. I spent a night in Rome (each way) and then flew to Palermo and from Catania. You should find many more options from Chicago. Google Flights is very good at showing what’s available, and then you can book directly on the airline’s website.