The furthest ahead of Chicago one can get before crossing the International Date Line is the Line Islands of Kiribati or Tokelau, New Zealand, which are 20 hours ahead of Chicago when Chicago is on Standard Time.
I believe the furthest behind in time are the Galapagos Islands off the coast of Chile.
Kiribati's Line Islands Time and Samoa Summer Time are furthest ahead, at UTC+14.
There is no time zone 23 hours ahead of Alabama.
The easternmost time zone is only 8½ hours ahead of India.
If you count Iceland as a part of Europe, it is furthest west. Otherwise, the furthest west European country is Ireland. The furthest west country in mainland Europe is Portugal.
Singapore
Brazil
Malaysia
Antarctica is the furthest south continent in the world, with the South Pole located at its southernmost point.
Nepal
Asia is a continent, not a country. No countries from Asia are members of the European Union. Cyprus is the country in the European Union that is furthest from Ireland.