Fly into Chicago O'Hare Intl. Airport (ORD), the closest airport, located 20.5 mi (33.1 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago Midway Airport (MDW), which is 5.3 mi (8.6 km) away.
If you'd rather travel by train, make your way to Chicago Gresham Station or Chicago Brainerd Station to see more of the city.