ana Shanghai flies to Cleveland and connects through Chicago. Do I need to pay again if my luggage is too important?

1. Is the arrangement with ANA and United Airlines a connecting flight? Even if it is two airlines, it can be a connecting flight. If it is a connecting journey, you can pay once in Shanghai. After getting off the plane in Chicago, you have to go through immigration procedures, go through the immigration office to check your passport and visa, then collect your luggage, go through customs to check the substances (contraband and possibly taxable items), and then deliver the luggage.

2. If it is not a joint trip arrangement. In Chicago, you must bring your luggage to the UA counter and re-deliver it. There is no free checked baggage on U.S. domestic routes. There is a fee for each item.

3. By overweight, do you mean that each piece of luggage exceeds the weight limit of 22 kilograms? Or, ANA only has one piece of 22kg for free, and you have two pieces. The two pieces are not overweight, they are oversized. The calculation for overweight and overweight items is different.