How I Check the Weather
Start Small
Check METARs and TAFs at the airport you're planning for as well as a few others surrounding Indy.
Go Big
Look at Prognostic and Surface Analysis Charts on the Aviation Weather Center— What's causing the weather or what weather is on the way
Read over the Aviation Forecast Discussion
Check Other Sources
Check Winds Aloft/Temps Data— Looking for strong winds and temperature inversions
Check Graphical AIRMETs and SIGMETs
Look for severe weather and convection activity
Review any PIREPs
Check the NWS Hourly Weather Forecast
1800wxbrief
It should go without saying that getting a weather brief from 1800wxbrief is highly recommend. Whether you call or visit the website, get one.
P.S. "Today, the Internet gives us myriad-mostly informal-sources to figure out the weather for our flight. Here's what to look for as you brief the weather." Read more on IFR Magazine
P.P.S. wttr is a fun 3-day view of the forecasted weather. It can also do a bunch of other neat stuff. See GitHub.
P.P.P.S. There's no such thing as a "legal" weather brief.