We have always driven in from MI where we live, but many of my friends in MI and IN take the Southshore train line into the city since it means they don't have to worry about parking. We take the 90/94 tollway over the Skyway Bridge.
TO drive or not to drive, that is the question. I approach it this way: If I’m going to the Loop or the North Side, particularly Cubs day games, I prefer to use public transportation. Anything on the South or West side I usually drive.
Get a map, learn it and create wacky short cuts, the Interstates occasionally resemble parking lots. Driving around the Loop, especially during rush hour, is a tiring game of skill, wit and perseverance.
Pictured: So rare I had to capture it in pictures. The Dyan Ryan, NOT clogged up.
Grant Park garage offers good discounts.
Cheap airlines for Chicago typically fly into Midway. Great fares can be found on American or united which fly to O'Hare. Spirit airlinse offers really cheap fares to O'Hare as well.
Both airports are connected to the city by CTA subway. Midway= Orange Line and O'Hare= Blue Line
Buses are the most common method of public transport. The #151 is very useful for tourists. It goes from Union Station, to State Street, to Michigan Avenue to Water Tower Place to Lincoln Park. Downtown Chicago is easily and best viewed on foot.
For a Lake Shore Drive ride, you can take the 145 or 146 express bus (picks up on State St or Michigan Ave) and it goes on the outer drive to Belmont. Get off at Belmont and you can walk to Lincoln Park or catch the same bus or the slower 151 back downtown to your hotel.
The subway can be confusing because stops do not have unique names. 'Chicago Ave' on the blue line is entirely different station from 'Chicago Ave' on the red line. Be certain which stop you want on what train line.
Coming from St. Louis, we drove. Although they do have a large airport. And even a large train station that I did go through in my younger days.
There's the famous, and popular, L (elevated train). My husbands used that on various business trips.
But driving in Chicago really wasn't bad, so I'd recommend renting a car while there.
There are three ways of getting into Chicago:
1) Driving. The signs are clearly marked and getting into the city can be easy. Can also be a hassle as gridlock is becoming all too frequent.
2) Taxis. The easiest and the most expensive.
3) Train. I don't often take the train to the airport, but I hear it is quite easy and cheap. It is called the 'yellow line' just ask the information desk in the airport and they can direct you,
Trains/Buses: Are the cheapest and although I am not familiar with the routes, the CTA (Chicago transit authority) can tell you what route is best.
Taxis: Are the quickest but are expensive and can be an adventurer - like an amusement ride but in traffic :))
Bicycling: Although the mayor recognizes that there needs to be areas for us, the city is not conducive to bikers - be careful
Seen on I-290, known as the "Ike" -- heading home to Chicago ...
For up-to-the-minute information on area road congestion consult the website listed below.
It makes things much easier to see when you have your own personal driver even better when its a beautifull woman ...................
Gas stations are few and far between in downtown Chicago -- this one is on the corner of Congress and Dearborn. You can also note the condition of Chicago's streets :(((
This is the Monroe Avenue bridge over the Kennedy Expressway, as it enters the city from the north. As this is the main expressway into the city from the northern suburbs, the traffic is constant.
Chicago's traffic can get pretty bad...especially in the summer. In addition, there are several highway road construction projects that will cause driving delays through the end of the summer.
The traffic in Chicago is horrible so riding a bike, rollerblading or just walking are probably the best ways for getting around. :-)