Public transportation/fares: Chicago's grid of north-south and east-west streets and logical system of address numbers makes finding your way around fairly easy The only complication: The occasional diagonal avenue that cuts through the grid of horizontal and vertical streets. Chicagoans often give directions by telling you to head north or south, which can be confusing to out-of-towners. The key is to always keep track of which direction Lake Michigan is, which will help you keep your bearings. (If the Lake is to your right, you're heading north, and if it's to your left, you're heading south.)
Public transportation in Chicago is reliable and extensive, including trains and buses that cover most of downtown. The El train system is a network of color-coded train lines (some elevated and some underground) that connects The Loop with surrounding residential neighborhoods. Check train schedules for hours of operation since not all lines run 24 hours. Some lines are undergoing renovation so service may be down or certain stops may be closed. Time Out Chicago has an up-to-date bulletin on El schedules and routes, and also includes detailed public transportation directions to attractions, restaurants and nightlife throughout the city.
Buses run regularly throughout downtown (the stops are marked with blue-and-white signs). Commuter trains provide a quick, pleasant ride to the surrounding suburbs. The fare on trains and buses is $2 each way; buses will not give change, so be prepared to pay the exact amount. Visit the Chicago Transit Authority Web site for maps and route information.
Taxis, on foot, or by bike: As in other big cities, taxis are helpful (and readily available) if you need to drag heavy luggage to your hotel or get across town relatively quickly at night.
You can flag down a taxi relatively easily throughout downtown Chicago. If you have trouble spotting one, you should head for a major thoroughfare such as Michigan Avenue or State Street. Taxis charge $2.25 for the first mile and $1.80 for each additional mile.
If you're staying downtown and visiting the city's main museums, you can get around quite easily by walking. Many of the best museums and restaurants are within walking distance of The Loop and Michigan Avenue.
Biking is a popular summer hobby along the lakefront bike paths. Bike Chicago has rental stands at North Avenue Beach, Navy Pier, and Millennium Park if you feel like pedaling as you enjoy the view.
Personal or rental car: If you decide to rent a car to get around during your stay or drive in to the city, be aware that day time and overnight parking rates in the downtown area can be high, although many hotels offer discounted rates to guests. Be sure to check street parking signs especially if you opt for on-street parking overnight and even during the day. There are many intricate parking regulations, such as no parking on major streets if there is more than two inches of snow; no parking on the south side of major streets from 7:00 to 9:00 a.m. and on the north side from 4:00 to 6:00 p.m.; street cleaning from 9:00 to 3:00 p.m. once a month.
Also, be sure to carry a roll of quarters for metered parking. Although not easy to find, especially downtown, you can save a bundle over garage parking rates, but beware that most metered parking spots have a two-hour limit. The City has an aggressive parking violation patrol, and taking chances is just not worth the excessive fines if you break a rule and get caught. Also, be very cautious not to park in private parking lots that have "Violators Will Be Towed" signs, yellow tow zones or near fire hydrants. It takes only a few minutes for a tow truck to be dispatched, and the fines to get the car out of impound are upwards of $100, plus you may also have to pay a parking ticket.
HowStuffWorks "Getting In, Getting Around Chicago"
This site has a lot of neat information:
Summer 2009: Explore Chicago | Ways to Explore