Chicago O'Hare to start in Florence for Tuscany tour

When we were concluding our recent trip in Lucca, we flew from Milan. Just another option that might be worth considering. Have a great trip.

All airports have bad reviews, it does not sound like you read the reviews of O'Hare or O'Hell as some people refer to it. Are the bad reviews related to what happened to people when they arrived and got off the plane at Florence airport?

You would have to connect from an airport in Europe anyway if you wanted to get a flight to Florence. Otherwise you can only get a direct flight from O'hare to Rome and then take two trains to get to Florence. One from the airport to Roma Termini station and then one from Roma Termini to Florence. It is best to buy the train ticket when you get to Rome.

THis is amazing. We flew out of the Florence airport. It was a pretty normal airport, a little small for such a big important city. We had no issues whatsoever. There is a marvelous tram from near the bus station to the airport. It's all good.

As AI said, all airports have horrible reviews, just as all airlines have horrible reviews.

In defense of Chicago O'Hare, unless you're connecting at O'Hare, the airport is easy. Many international departures are from the domestic terminals. On your return, arriving at the International terminal is easy, with Global Entry I'm through immigration way before the luggage carousel starts moving.

Back to your question JP,

You can either fly nonstop to/from Milan or Rome. This would allow you to spend some time in either city before your train to Florence.

If you are okay with a change of planes then fly from Chicago to Florence and return home from Pisa or Florence to Chicago. Just choose your connecting airport wisely.

Unless you have been before, my vote would be nonstop to Rome. Spend a few days in this beautiful city. Then train to Florence. Return flight out of Pisa or Florence to Chicago.

Can also fly in or out of Venice

We had a tour of Tuscany and Umbria a few weeks ago and chose to fly direct from Atlanta into Rome then take the train to Florence. Had we elected to fly into Florence, we would have had to change flights, likely in CDG or Amsterdam.

The train ride was an hour and a half, but of course, we had to take direct train from the Rome airport to the central rail station.

You can go to Kayak or Google Flights, enter from ORD to Florence (FLR) or also nearby Pisa (PSA) and check prices for your dates.

Then you can do the same using Rome-Fiumicino (FCO) or Milan-Malpensa (MXP) or Milan-Linate (LIN) as your destination. Then compare the prices and the convenience of flights and decide.

Consider that from ORD there are no stop flights only to FCO or MXP.
FLR, LIN, PSA only have Intra Europe flights, therefore a layover will be necessary to those.

FCO is closer to Lucca than MXP. The train from Rome FCO airport to Lucca will cost you at least $75 per person one way, more if you arrive at Milan MXP. So take that into consideration when you compare prices.

No matter which flight you choose, you will need to spend the night before the return flight near the airport where you depart from, as flights to the US depart in the morning and Lucca is too far from any airport with the exception of Pisa (40 min).

I think flying into an airport is not the issue. Flying out of an airport can lead to
lines for baggage check, security, immigration. But it sounds like you will not be
flying out of Florence.

Any issues with the Florence airport are likely to be small compares with the delay
you will have if you fly into an alternate destination such as Rome and deal with the
crowds, multiple train connections, etc. As you say yourself, you are novice travelers,
so avoid the hassles.

No matter your destination in Italy, airport strikes are a thing to be aware of these
days.

On the return, depending on schedules and airfares, you might look at Pisa.
Closer and less hassles, but fewer connection options.

I traveled to Florence from Chicago last September. I flew to Rome, took the Leonardo Express train from the airport to Termini and then took and an Italo train to Florence. 20 minute walk to our hotel in Florence.

It was really easy. Easy to find the train at FCO. Lots of uniformed helpers at the train station. Termini is big but IMO easy enough to navigate (tons of You Tube videos to help) and there are lots of high speed trains to Florence.

I have not used Florence airport. On another trip I flew from Pisa to Chicago via Munich. Pisa airport is small and user friendly.

I think it would help for our answers if we knew if you wanted to visit any other place in Italy or just your tour. Or what your travel experiences have been. Flown several trips in the US, experience with trains, etc.

Your choices seem to me from what we know is fly into a bigger city nonstop, Rome or Milan and train to Florence, or only from Chicago into an intermediary airport such as Munich, definitely not Paris or London, into Florence.

Tuscany is amazing as is all of Italy. I hope you plan on arriving at least two days or more before your tour so you can get over jet lag and be ready to go at the start of the tour.

There is a huge amount of experience on this forum. I am a minor contributor but let us know how we can help you.

We won't have extra time to spend before the trip or after except for the day or two before to jet lag and home after. We want to use O'Hare the Friday before and arrive in Florence by Sunday and then leave Friday from Italy to get in Chicago over the weekend.

I wouldn’t worry about the airport in Florence. If it was me, I would fly into Florence via a connecting airport in Europe. Again, flying out of Pisa via a connecting airport. All on one ticket. Multi-city into Florence and out of Pisa.
Good luck and I am sure you will have a great time,

I’ve flown in and out of Florence Airport perhaps 6 or 7 times in the last few years.
It’s no worse than any other one!
It’s so easy to get into the city from there by the tram “TramVia”.

The Florence airport has a real issue: as it was not planned to have an international airport there from the very beginning, it has a really short runway. So no big planes out or in (most are A319s) and if visibility is scarce or the runway wet, pilots will consider landing at an alternate (Pisa or Bologna) especially if the plane is heavy. But this an issue mainly in winter months and less likely to happen in September.

We have flown in/out of Florence many times without any issues, except this April. As stated above the pilots can decide if landing could be a problem. We were flying from Amsterdam and somewhere along the journey it was decided the winds were to strong for a safe landing and we were diverted to Pisa. The airline arranged for transfer to Florence by bus. We arrived in Florence only about an hour and half late. It was all very well organized.

You made the following two posts

We are novice travelers and want the experience to be smooth and as stress free traveling to and from these destinations.

We want to use O'Hare the Friday before and arrive in Florence by Sunday

Pick one.

If you want "stress free" then you want padding which means flying out Thursday so you arrive in Florence on Friday. This provides flexibility in case there is bad weather in Chicago or Florence, a mechanical issue with the plane, a crew issue, you name it. Experienced travelers aim to arrive in Europe at least two days before something like the start of a tour or cruise. There was a frazzled couple on our RS Sicily trip that had spent 3 days trying to get to Europe due to storms (and this was in Sept) but finally got there the afternoon the tour started with the meet-and-greet.

I'll add that as novice travelers you probably don't know how jetlag will affect you. As a couple you're spending over $8,000 for this tour. An extra nite or two before the tour is a small cost compared to this but can add greatly to your energy level and readiness for the tour.

If you can get non-stop flights, choose Rome or Milan or open-jaw with both. If there's no major price difference or better flight departure/arrival times, it might be a toss-up. There are a few direct trains from FCO to Florence, but because of their relative infrequency, you may end up having to take a train into Rome, then on to Florence. From MXP, similarly, you have to get to the train. It takes about an hour longer from Milan than from Rome. From Lucca, you'd probably take the train to Florence, then reverse the arrival sequence back to the airport.

If you have to connect, take a look at Pisa and Bologna as alternatives to Florence. Both are pretty close the Florence and Pisa's close to Lucca. I'd avoid connecting at a US airport - too many hassles with customs, immigration and changing terminals.

I've flown in and out of O'Hare every year or two. Terminal 5 is easy and only once did I have a long wait when I landed at ORD around 5 pm on the Friday of Memorial Day weekend. It was inexplicable and the only time in or out that was difficult.

To me, smooth and stress-free would mean flying into Florence airport and then going to your hotel.

We love the Florence airport because it is so small and so close to the center of the city --- we just flew to and from it again last November/December without problems. It's such a welcome relief to simply land at your final destination instead of landing and then having to keep traveling on and on and on when you are tired and/or jet-lagged.

Also, if we avoided everything with poor reviews, we wouldn't be able go anywhere or eat anywhere or buy anything. Seems like way more disgruntled people than happy people are moved to write reviews.

To tell it all, not only the Florence airport is more reliable in summer than in winter, but also some companies are more reliable. For example, my brother lived in Paris and he has seen over several years that Air France was less likely to be diverted from landing in Florence in bad weather conditions than low cost companies. There is probably a technical reason, that there is a software mod for the Airbus A319 flight control program called the "Florence kit" that allows for lower landing speed with heavier airplanes on very short runways (it is said to be used also at Santos Dumont in Rio de Janeiro and at Gibraltar), but not all companies have it.