Chicago Midway airport (MDW) feasibility to/from Greyhound Bus station?
score:4
When I read your previous question last year about traveling to CMX, I had absolutely no idea just how bad an airport in the US could be...
Flights in and out of your local airport (CMX) apparently have the worst on-time record in the US. This seems a little odd when there are only two arrivals and two departures daily, they're all United Express/SkyWest, and they are all to/from ORD. But your airport has issues. It's an untowered airport with no ground radar or ground weather services, and apparently an automated weather sensor decides whether the airport will be open or closed. Which is a little strange since the airport does have ILS. And neither the airport nor the airline seem particularly interested in improving service.
Nearby airports aren't much better. SAW (aka MQT) is only a few hours away on an Indian Trails/Greyhound bus ($18 each way, and you'll need a taxi), but it's also on the aforementioned list of worst on-time airports. ESC is even farther away, and suffers many of the same weather-related issues. IMT is apparently not reachable by public transit at all. And RHI, while relatively close as the crow flies, public transit takes so long to get there that you would be as well off just going to Chicago.
So, you may as well go to Chicago, which you have planned to do. Your itinerary looks reasonable. The only thing you may want to be aware of is that your hostel is 1.9 km away from the Greyhound station (which does not map correctly on Google Maps; it is actually here). While this can obviously be walked, if you have two large bags and a smaller one you may wish to take a taxi anyway; note that taxis in Chicago are metered and have teal number plates, and this should be quite a short trip.
I would definitely recommend the travel insurance if you decide to use any of the regional airports. While it won't guarantee you get there on time, it may help you cover the costs of getting there if you are diverted to another airport, a hotel if your flight is cancelled, etc. In fact, you probably should have travel insurance even if you fly out of Chicago, just in case.
P.S. Remember to check your visa expiration and renew it if it has expired or will expire before you get back.
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