I need help from experienced travelers -

We just booked some tickets to Italy because the price was too good to pass up, but now I'm worried about the connection time.
Here's the itinerary -

Thursday, June 11, 2009

San Francisco International (SFO) to Chicago O'Hare International (ORD)
Departure: (SFO): June 11, 8:50 AM PDT (morning)
Arrival: (ORD): June 11, 2:54 PM CDT (afternoon)
Class: Economy

Thursday, June 11, 2009
Air One # 21

Chicago O'Hare International (ORD) to Milan Malpensa (MXP)
Departure: (ORD): June 11, 4:55 PM CDT (afternoon)
Arrival: (MXP): June 12, 8:35 AM CEST (morning)
Class: Economy

With the change in airline - do we have enough time to make this flight? Please tell me yes!

Which airlines?

When you say changing airlines - are your tickets booked as ONE trip through one airline (and codeshare on the other leg), or did you book them separately from 2 different airlines?

Makes a huge difference.

I'm not sure and now I feel really stupid -

I booked them online - started at Kayak.com and then was sent to cheaptickets.com - they priced it as one trip the first leg is United from SFO to ORD and the second leg is Air One to MXP - I have 2 hours in between flights.

Will I have to pickup checked luggage, recheck at Air One and go through security again?

You need to contact the airlines in question and find out the details. ORD has an international terminal and it doesn't sound like you will be landing there. So - yes - you may have to pick up luggage, change terminals, check in again and go through security.

Call the airlines NOW and get the info. If this is not a doable connection your chance of fixing it somehow is better now than later.

Most international flights depart from terminal 5 and United usually uses terminals 1 & 2.

If your luggage is checked all the way, you need to get on the tram and go to terminal 5. I've flown via ORD with similar connection time with no problem but it has always been on the same airline.

I checked out the United website and it shows the second leg of the flight as operated by Air One - so I think I am OK and that the luggage will go all the way through and we'll just have to connect to the flight -

Thanks for the advice!

Whew - big sigh of relief! Now the fun trip planning can begin!