O'Hare is 27km from The Loop (the downtown core) and Midway is about half that distance. Chances are you'll be arriving at the much larger international hub, O'Hare, but transportation into the city is still pretty easy. Though cabs are plentiful, there are no flat rates – expect to spend about $35 to $40 to get into the city. The blue line of the "L" stops at O'Hare and at peak traffic times it might be the fastest way to get where you're going.
The second largest system in the U.S., Chicago's CTA makes getting around on public transit a cheap and easy option. The famous "L" trains are the system's defining feature. The first elevated trains began running in 1892 and have since shaped the evolution of the city as the train's multi-coloured network radiated out from the core. The "L" now services 144 stations 24-hours a day, each one the hub of a neighborhood. The fare is $2.25.
Taxis typically aren't hard to come by in Chicago. There are 7,000 of them within the metro area and they're readily hail-able from major thoroughfares. The "flag pull" fee is $2.25, then it's $.20 for each additional 1/9 of a mile. Wait time is $.20 for every 36 seconds.
Yellow Cab Chicago: 312-829-4222
Checker Taxi Chicago: 312- 243-2537
Chicago Carriage Cab: 312-791-1273