This guide is a slightly edited version of pages we created for out-of-town guests to our wedding on August 5, 2006. Thus, some of the information may be dated.
Chicago has two airports: O'Hare and Midway. Midway is less chaotic and easier to get to than O'Hare, and the discount airlines (e.g. Southwest) fly into Midway. O'Hare's saving virtue is the large number of flights that service it.
Airport Ground Transportation
Public transit (the CTA "El") into Downtown:
- O'Hare: The Blue Line runs from O'Hare to Downtown in around 45 minutes.
- Midway: The Orange Line runs from Midway to Downtown in around 30-35 minutes.
Driving a car into Downtown:
- O'Hare: Take I-290 East then I-90/94 East into Downtown. 25-30 minutes with no traffic, 1-1.5 hours with traffic.
- Midway: Take Cicero North until you hit I-55, then go East on I-55 until you hit I-90/94. Head West on I-90/94 into Downtown. 20-25 minutes with no traffic, 45 minutes with traffic.
Taxis: Taxis are moderately expensive (around $45 from O'Hare to the Loop); we've had good experience with Yellow Cab (312-TAXICAB). More on taxis and other hired vehicles can be found at World Airport Codes (note there's some information there on Midway too, not just O'Hare).
Car or no car?: Chicago, unlike New York, is drivable, though there is almost always congestion on I-90/94, particularly as you near Downtown. However, Chicago, unlike Los Angeles, does not require you to drive. Public transit is good.
Layout: The freeways in Chicago extend radially outward from Downtown at the Lake. Locals are mostly arranged north/south. Generally, north/south streets are named, east/west streets in the north side are named, and east/west streets in the south side are numbered.
Traffic: Generally, if you can avoid the freeways you'll do better. Lake Shore Dr. is a wide N/S arterial that has few lights, less traffic than the freeways, and is an amazingly scenic drive along Lake Michigan. If you're not too far from the lake, it's the quickest way to get from Downtown to the north side (where North Park University is) as well as the south side (where University of Chicago is).
The freeway congestion map provides real-time measurements of traffic flow along the freeways and Lake Shore Dr.
Parking: Downtown parking is expensive and there's little street parking. If you're coming to Downtown on a weekday, leave the car at home. On a weekend, same thing, though on a Sunday evening there's quite a bit of street parking Downtown.
Street parking throughout the city is hit or miss. Near high traffic areas like Wrigley Field, you won't find much. Watch meter times (they often go past the end of the workday) and tow zones.
Chicago's public transportation system is excellent. Chicago Transit Authority (CTA) buses and subway/elevated trains are the options in the city, and the Metra Rail trains connect the suburbs with the city. The Regional Transit Authority (RTA) provides a public transit trip planner you can use to figure out how to get from anywhere to anywhere in the area.