In the event of an emergency that impacts a wide area, broadcast radio and TV will generally be your best source of information. Kendall County is close enough to Chicago that you should be able to receive the major Chicago radio and TV stations. A GMRS radio won't help you with that, though some have the ability to receive FM broadcast radio.
Another good source of information for your general area is NOAA All Hazards Radio, aka NOAA Weather Radio, on 162.400 through 162.550 MHz. Some GMRS radios can receive NOAA Weather Radio, so you may want to look for that feature.
To maintain communications within a particular group of people, the key factor is distance. A "walkie-talkie" is going to have a limited range between radios, probably 5 miles or less. Talking radio to radio is known as "simplex". To get more distance between GMRS walkie-talkies, you'll need to use a repeater which makes you dependent on fixed infrastructure which may not be available in an emergency. Good antennas and elevation above ground can help increase the distance over which you can communicate with GMRS walkie-talkies, but you'll still be limited to maybe 10 miles. And, don't forget that if the SHTF, everybody else will be trying to do the same thing as you and there are only so many GMRS channels available.