Chicago Midway is another airport that I've either...

Chicago Midway is another airport that I've either taken off from or flown through too many times to count. This airport could benefit from an update, but there is construction and signage all around about modernizing it. Overall I really can't complain, there are plenty of local and chain food/retail options. As a plus the employees I've interacted with have been very helpful and friendly. Even on the occasions when I've arrived at Midway to a long line at security, it still seems to move quickly enough. There is also easy access to the CTA Orange Line which will get you to the downtown loop where you can transfer to the Metra in about twenty minutes or so. Compared to most airports you're set when you take off or land.