Basic English on the plane should not be difficult, just ask what you want to eat and drink.
When you enter the customs in Chicago, you may ask the customs officials hello, or you may say nothing but what they ask.
After talking about luggage, you need to ask if you can catch your flight or something when you may go to the next flight. You can ask the staff at the airline counter to give him the boarding pass from Chicago to Boston and ask:
You can invite (in many ways, you can invite, you can invite, and so on. Could you check this flight for me? Ask him to check your flight.
Can I catch it? Can I catch it?
Which door? Which boarding gate? (Because 99.99% of the boarding passes from Chicago to Boston are not marked with the boarding gate)
If you can't arrive on time, they will automatically change your ticket to the next flight. You can also ask:
When is the next flight? When is the next flight?
You may ask how to get to your boarding gate, just ask:
Excuse me, do you know how to get to the boarding gate ... If you ask someone who you are not sure knows how to get there, just ask.
If you ask the staff at the counter, they will basically know, so just ask, how to get there?
If you can't keep up with the times, be smart and use little English.