Here's a tip from someone who has taken the Orange Line from near Adams & LaSalle in the Loop to Midway 50+ times during the evening rush hour: Assuming you are able-bodied and can walk briskly (which I assume by the "only have a small backpack and will wear my comfy shoes" post) -- Don't get on the Orange Line at Quincy/Wells; instead, walk east on Adams and get on the Orange Line at Adams/Wabash. That way you'll be leaving the Loop as soon as the train starts moving instead of going almost completely around the Loop. And, you may catch the train in front of the one you would have otherwise caught. However, that time of day will likely mean a standing (instead of sitting) ride on the train to MDW.

And, check this shortly before you plan to and as you walk to the station: http://www.transitchicago.com/mobile...aspx?sid=40680

FWIW, I've made similar WN flights (6:25pm) leaving Dearborn & Adams at 5pm and made them without issue through the PreCheck line (usually on Fridays though).

Thank you! Yes, thankfully able bodied and able to walk quite briskly. And thanks for the link - it's now bookmarked on my phone. :)

I remember the walk from the DL gates to the station at MDW as being confusing as well as a long walk. Maybe it's easier in the other direction, but if you're flying into MDW, try to take some time to check out the route so that you're prepared on your return to the airport.

I'd also buy the ticket in advance so that you don't have to stop for that as you enter the station.

Thanks for the additional pointers. Flying in to MDW as well so I'll pay attention on my way out to the train. And I'll be riding the train around all week so my card will be loaded up.

Definitely easier from the station to the concourse, as there's essentially only one way you can go, whereas exiting from the terminal and navigating through the parking garage can be a bit confusing the first time.

If you're walking quickly and at the head of the pack, just know that when you exit the turnstiles at the MDW station, you're bearing to the right (up the stairs/escalator). Many will head left to the buses. Also, don't be concerned if you feel as if you're in an abandoned hallway and wondering if you took a wrong turn. I'm a fast walker and it's often a solitary walk.

Eventually, there are supposed to be concessions along there to replace the moving walkways that were torn out.

That moving walkway never really made sense to me. Why that particular stretch and only that stretch between the station and terminal? It's like Midway bought XX walkways for the terminal and only used XX minus 1, so they had to find a place to throw the last one.