The best way to get the Chicago experience is definitely on foot. Most attractions are within a reasonable enough distance to facilitate it, and there's a lot to miss stuck in a vehicle - the famous wind, the smell of Lake Michigan, the street vendors...
Driving a car is a hassle for a few reasons, the most obnoxious of which is the traffic. The Dan Ryan Expressway, leading into the Loop from the east, is continually congested and can be frustrating; if it's clear, though, be careful to watch the speed limits - you will be stopped and further annoyed by a speeding ticket. Parking is also kind of a joke, just like in the business district of most large cities. Be prepared to pay more than you were expecting to pay if you park in a garage. Street parking is a rare phenomenon, and if you're in town for a festival or special event, forget it completely. You're better off with public transportation.
Speaking of public transportation, there is a lot to go around in Chicago.
My favorite is the free trolley system. During the summer months, the trolleys stop all over the downtown area and provide service to major attractions. If you're feeling especially touristy, hop on one and visit whatever landmark it takes you to. That's pretty much all there is to it - hop on and go. Most run 10am-6pm and stop at places like Navy Pier, the Museum Campus, Lincoln Park Zoo, Michigan Avenue, State Street and Chinatown. One word of caution: not all the trolleys are free! Make sure the one you're trying to get on has a 'free trolley' sign in the front window and is stopping in front of a 'free trolley stop' sign.
Biking is also popular - when the weather is warm, anyway. 'Bike Chicago', an annual festival held to promote biking and all its glorious effects, is huge; Bicycling magazine has named Chicago 'best big cycling city', and there are events from May-June designed to encourage riding instead of driving. Buses have racks for bikes, too. Didn't bring it but want to ride? There are Bike Chicago rental places at North Ave. Beach, Wilson Ave. Beach and Navy Pier. Expect to spend about $35/day on a mountain bike, and remember that rentals are based on availability.
A Chicago oddity, the River Bus (312-337-1446) runs an 8-minute journey from the Michigan Avenue Bridge to Union Station from April to October for $2 a head.
For the traditionalist, though, good old reliable standard public transportation in Chicago is definitely a presence. Central Transit Authority (CTA) controls CTA buses, subway trains, surface trains, and "L" (elevated) trains. To ride any of these, you have to buy a pass for $1.75/trip, give or take a bit depending on the age of the passengers, holiday price gouges, and so forth. Bus stops are all over; subway stations can be found at major intersections like that at Monroe and State Streets; METRA surface commuter trains to the suburbs can be caught at Union Station, and the "L" trains run around the Loop and to nearby suburbs.
Both airports are serviced by rapid transit trains, with lines that can take you directly to the action. If you're leaving from O'Hare, you're taking the Blue Line, and no matter when you land, you're bound to catch one soon. Theoretically, you won't have to wait longer than half an hour (tops, on a holiday or in the middle of the night), and there are trains 24 hours a day. At the Midway station, though, if you miss the 12am train, you're out of luck until 4 or 5am. Other than that, there is pretty reliably continuous service to the Loop, and you can find an L train heading almost any general direction once you're downtown.
Chicago is proud of its public transportation system, and it shows. While it's never non-frightening to get on after midnight in a big city, people generally feel safe using all of it; even better, it's pretty easy to understand. Chicago has a lot of commuters, and even many people who can afford cars take trains and buses to avoid traffic headaches.
Taxis are also plentiful. Apparently there has been a recent increase in basic prices, but the rates are still reasonable, for the most part. You'll pay $1.50 before you go anywhere, $1.20 for every mile or 6 minutes of waiting time, and $.50 for any extra passengers. In my experience, cab drivers are friendly; however, it never hurts to know the shortest route to wherever you're going, in case your driver is into scenery. You can catch one downtown pretty easily, but if you can't, call Yellow (312-829-4222) or Checker (312-243-2537).
Almost all the public transportation in Chicago has discount or reduced fares for special circumstances. If you don't see, say, a student rate, be sure to ask - more often than not you'll save a buck or two. Sometimes cab drivers will agree to a flat rate for a long distance haul, and there is a shared ride program for carting passengers en masse from the airports to certain stops for one rate ($14 a person from Midway to downtown, $19 a person from O'Hare to downtown).
As long as you brush up on where you need to be to buy tickets and catch buses or trains, Chicago public transportation is neither too hard nor too expensive.
Questions?
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