Chicago Midway airport (MDW) feasibility to/from Greyhound Bus station?

I am a Michigan Tech student and live in Houghton, MI. I am in need of traveling to/from Midway airport in Chicago and need any feedback that may be helpful for me. I am carrying 2 big bags along with a laptop backpack. Here is my itinerary:

A) HOUGHTON - CHICAGO
1. Houghton[11:52pm, July 4]
2. Greyhound Bus station[1:30pm, July 5] {$65}
3. Chicago HI Hostel via Blue line[2:00pm, July 5] {$1}
4. Stay at HI for 1 night[checkout 9:00am, July 6] {$40}
5. Midway airport(MDW) via orange line[9:45am, July 6] {$1}
6. MDW flight depart[12:30pm, July 6]
7. MDW - DTW - CDG - BOM[11:30pm, July 7]

B) CHICAGO - HOUGHTON
1. BOM - CDG - ATL - MDW[2:20am, August 16]
2. MDW Flight arrival[6:40pm, August 17]
3. HI Hostel via orange line@7pm[7:45pm, August 17] {$1}
4. Stay at HI for 1 night[checkout 12pm, August 18] {$40}
5. Greyhound bus depart[7:15pm, August 18] {$72}
6. Houghton[8:45am, August 19]

As can be seen the cost of this itinerary is $220.

An alternative is a flight operated CMX-ORD for $300, but I have heard that it gets cancelled most of the times. So if I have to stay at one of the airport hotels than that cost will go much higher. I really do not have any expert advice available and so need any help available from all the helpful people here.

QUESTIONS

1. Are there any pitfalls/improvisations for the itinerary for the bus journey?

2. Is it advisable to take the flight option instead? I was just concerned if the flight gets cancelled or delayed, my international travel is in danger because it is not a connecting flight.

3. I have option of choosing travel insurance for $62 for the international flight from the same airlines. Would this ameliorate the risk of flight cancellation for the CMX-ORD flight?