My wife and I are relocating after she got a great job in Ann Arbor. I'm helping with a transition at work and am going to spend part-time in the Chicago office (2 days a week) and work remote from Ann Arbor. Wondered if utilizing Amtrak or Megabus would be a decent method to commute back and forth versus putting all the miles on my car (it's a lease and commuting monthly equates to 2 months of leased miles). Flying is a bit outside our price point.

Thoughts?

I have taken the train to Chicago from Detroit. If you can travel on weekdays, the train seems less crowded and you may be able to work on the train. The farther ahead that you buy your tickets, the cheaper they are. They also have a frequent traveler program. The only downfall is that you don't always get to your destination at the scheduled time. My return trip to Detroit, in December was delayed about 2 hours due to snow.

The "Saver" tickets on the Wolverine are as low as $31 buying at least 2 weeks in advance. The regular price ticket is $93 each way. If you can work 2 consecutive days, you could arrive in Chicago about 11AM CT on the early train and return to Ann Arbor the next day on the late train. The HI hostel on Congress is the largest hostel in the US and has private and dorm rooms available.
If 10:30-11AM CT is not early enough, you could take the Sunday train and spend an extra night in Chicago