San Diego to Chicago is about 2600 miles, so it’s probably about the same for Indianapolis, maybe more. But the good news is that Adventure Cycling has a route planned for Santa Monica to Chicago, so it would take much to tweak the route by just breaking off at Springfield and riding to Indianapolis (I’ve done Springfield to Indy myself): https://www.adventurecycling.org/routes-and-maps/adventure-cycling-route-network/bicycle-route-66/
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San Diego to Chicago is about 2600 miles, so it’s probably about the same for Indianapolis, maybe more. But the good news is that Adventure Cycling has a route planned for Santa Monica to Chicago, so it would take much to tweak the route by just breaking off at Springfield and riding to Indianapolis (I’ve done Springfield to Indy myself): https://www.adventurecycling.org/routes-and-maps/adventure-cycling-route-network/bicycle-route-66/
It wouldn’t be hard to adapt Adventure Cycling’s other routes for a San Antonio to Indy route, either. Their [Southern Tier route](https://www.adventurecycling.org/routes-and-maps/adventure-cycling-route-network/southern-tier/) would get you to the Mississippi River, then north on the [Great River route](https://www.adventurecycling.org/routes-and-maps/adventure-cycling-route-network/great-rivers-south/) to St. Louis, then the Route 66 to Springfield.
Obviously, you can buy the maps you need and make whatever variations suit the group.