Originally Posted by FindAWay

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).