on the way there i am going from manchester to chicago, then releigh durham
the way back will be louisiana to huston texas, chicago to manchester.
I think i will have to take it, it is only light and folds really well, i am trying to take as little luggage as possible, but finding it hard.
Ah, O'Hare, my sweet spot. If you know the airlines I can give you even more specific information. Transferring in Houston, TX I am not as good at. I would guess either Southwest or American Airlines for that leg of the journey. If you are changing airlines in either it is going to be a LONG LONG walk.
O'Hare you will arrive at Terminal 5. You will have to go through customs and pick up your luggage and then exit out the door and recheck it onto the next flight. If you are using United Airlines to Raleigh it most likely will leave from Terminal 1. At least that is where you will have to go through security. You get there by a tram. Both Terminal 5 and Terminal 1 have very long walks to get to the train and from them. You cannot even get an electric shuttle from most of the places. If it is American, then it is Terminal 2 and basically the same story.
As far as the return trip, like I said, I don't know transferring in Houston well, I have only arrived and left from there on United Airlines and there are only a few gates. But I don't think you are using United there, because there are no Louisiana->Houston flights. That is more likely American or Southwest.
If you are leaving to Manchester via American or United, then the return from Chicago is going to be easier, because the flights for those leave from the same terminals you would arrive at (except there maybe a long walk even between gates there). If you are returning to the UK on another Airline then you will have to go from your incoming terminal and go to Terminal 5, another long transfer as well as a second security screening.
Basically I would bring the stroller with you no matter what. As Kathleen mentions you can always put your carry-ons in it as well as you are likely to be standing in lines at one point or another for a long time and little 4yo legs do like to get tired!