Bloomington does not have commercial airline service. The nearest airports are Indianapolis (about 60 miles north) and Louisville, Kentucky (about 55 miles southwest). Both have rental cars, and the drive to Bloomington takes about an hour from either. There is bus service between Indianapolis and Bloomington several times daily.
By car from Indianapolis: take I-465 to SR-37 south (now converted to US-37 freeway standard), which runs directly into Bloomington. The drive is straightforward and takes about an hour. From Louisville, take I-64 west to SR-37 north.
Amtrak does not serve Bloomington directly. The nearest Amtrak station is in Indianapolis.