Getting To Chicago

BY PLANE
Chicago is served by two airports: O'Hare and Midway. Neither one is particularly close to where Ryan and Ryan live, so dealer's choice on which one to fly into (in this case, you are the dealer).
Both airports have CTA train service; from O'Hare, take the Blue Line, and from Midway, take the Orange Line. The trains will be easy to find because they are very large, and also, there are many signs. Conveniently, each airport is the end of their line, so you don't have to figure out which direction to take it: just get on board!
Both airports are also served by taxis services. We recommend a taxi over a ride-share, as taxis have set rates, and opposed to ride-shares, which hike up their rates at the exact moment people really need to use them.
BY TRAIN
Chicago Union Station is served by Amtrak and Metra, and offers an easy connection to the rest of the city via bus or the nearby Blue Line.
BY CAR
Have at it: https://www.google.com/maps
BY FOOT
Start walking now.