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I did this one in November. It is a long long hike from plane to el platform. 40 min ride to the loop and then 3+ blocks from Quincy station (on Wells) to Union Station.

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Might he be able to get a red cap at the airport to at least take him close to the train. Then catch a bus after getting off at Quincy?

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The Midway CTA station is a bit of a hike from the airport. You have to go through a parking structure and then down an enclosed elevated walkway, through the station and then down steps, an elevator or an escalator to get to the train platform. At Quincy, I don't believe there is an elevator, so you have to go down stairs, then walk about three blocks to the station (including going over the South Branch of the Chicago River). If you have trouble waking, it would be much better to take a cab.

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Not many of the 'L stations in the southwest part of the Loop, are accessible. Closest nearby Orange Line station to Quincy that's accessible, is Washington/Wells (next station after Quincy). You always could request an Uber/Lyft/cab, to get over to Union Station.

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Best bet is to take Lyft or Uber if you have difficulty walking. It's a long walk from the gate to the midway el station. Then another long walk from Quincy. At Quincy there are no escalators or elevators. Just stairs.

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