From Chicago To Portugal - Should we fly to Lisbon (requiring a plane connection) or fly to Madrid and drive?
 

Next June my husband, 13 yo son, and I are most likely going to Portugal for vacation. We have not decided how many days but it wil probably be around 10 nights not counting travel days.

Our options are;

Fly from Chicago on TAP (United) to Newark and change to TAP flight to Lisbon. My concern here is the time between flights is less than 2 hours and with the flight leaving from Ohare - on time departure is a realistic concern. Also means we will spend better part of a day flying.

Fly to Newark on another airline on an earlier flight and leave on TAP from Newark. Will cost more but more likely not to miss the outgoing flight to Lisbon.

Fly direct to Madrid (Iberia) and drive to Portugal. Probably spend the first day somewhere inbetween in Spain.

Would like some advice on this and also would like to know how the drive is from Madrid to Portugal - which is the best way to get to the border etc.

Thanks in advance

I would find a way to fly directly to your destination, since I really hate driving after a long flight. Your time is short on this trip, I wouldn't want to spend a day of it driving if it isn't necessary.

I just did a quick search on orbitz.com and as you mentioned, Iberia has a non-stop flight to Madrid, but then a connecting flight to Lisbon. Please check it out, I think this is a lot better than driving.

As for your question about the border, there is no real border between Portugal and Spain as they are both in the Schengen zone. It's like driving from one state to another.

I'm still looking at orbitz.com and you've got tons of options for getting from ORD to LIS with only one stop along the way. Of course, I don't know your travel dates so I can't do a cost comparison but please check a few sites like orbitz.

Will look at that option - changing in madrid.

I would only fly to Madrid if you actually want to see Madrid. But Madrid is worth seeing, even for just a night or two.

I actually did the reverse trip last month, flying into Lisbon and out of Madrid. My husband and I spent two nights in the Alentejo between Lisbon and Madrid, and liked the area so well that we want to go back for a longer stay.

The drive from there to Madrid was a few hours on a highway, no problem driving it.

You might be interested in my trip report:

http://www.fodors.com/forums/threads...p;tid=35062668

Hello again.

Actually you could fly non-stop from ORD into several European cities, then connect to LIS. But Madrid would be my first choice since it's the closest.

Nikki - Hi - i did read your trip report and loved it.

I am loathe to change planes and am usually able to avoid it as Chicago has lots of options. I think I have to weigh the amount of time spent getting there with a plane change against the amount of time driving from Madrid to Portugal and back. We would not mind seeing a bit of spain along the way either.

I appreciate this advice very much.