O'Hare International Airport (ORD), is 17 miles northwest of downtown. Serviced by international and domestic airlines. The CTA Blue Line train runs 24 hours to downtown Chicago taking around 45 minutes.
Chicago is also served by local bus transportation. By using Bus and Train, any area of Chicago can be reached. The main Greyhound terminal, which has interstate bus service, is at 630 Harrison and Jefferson. There is also one at 95th/Dan Ryan red line station. Bus service provides transportation to many small cities and towns as well as the rest of the country, but is not a recommended form of travel for reaching other areas. 6 hours to Detroit
Chicago's Union Station is the hub of Amtrak's Midwest routes, making it one of the most convenient U.S. cities to visit by train.
I-55 will take you directly from St. Louis into downtown Chicago. I-90/94 comes in from Indiana to the east - but if you are traveling from the southeast, save yourself the frustration from THE WORST traffic congestion in the Midwest and take I-74 west from Indianapolis (not I-65 that takes you up to I-80 and I-90/94), heading west into central Illinois. As you pass through Urbana-Champaign I-74 intersects with I-57, and from there Chicago is a mere 2 hours drive north. I-90 comes in from Madison, WI to the west. I-94 comes in from Milwaukee, WI to the north. I-80 will get you to the city from Iowa.
If arriving downtown from Indiana, from the south on I-57 to the Dan Ryan Expressway, or from the north, Lake Shore Drive provides a scenic introduction in both directions, day or night. The shore and skyline are not to be missed. If arriving on the Stevenson Expressway (I-55) from the southwest, or on the Eisenhower Expressway (I-290) from the west, the skyline may also be visible from certain clear spots, but without the shore view.
Navigating Chicago is easy. Block numbers are consistent across the whole city. Chicago is divided east-west by State Street and north-south by Madison Street. Standard blocks are an 1/8th of a mile long. Each street is assigned a number, e.g. Montrose Av = 4400 N, which the address system is based on. Therefore, addresses can be used to estimate distances; in general a mile is equivalent to a street number difference of 800. The only exceptions are the distance between Madison St (0 N/S) to Roosevelt Rd (1200 S), and between Roosevelt Rd and Cermak Rd (2200 S); the distance between each is one mile.
Public transit consists of Chicago Transit Authority (CTA) trains and buses, Metra commuter trains for the suburbs and Pace suburban buses. They are all overseen by the Regional Transportation Authority (RTA) . You can plan your trips online at the RTA trip planner or get trip-planning assistance and information by calling 836-7000 in any local area code between 5 AM and 1 AM. Many visitors find the only public transit services they need to use are the CTA services, mostly the trains.
Most CTA rail tracks are elevated above ground level and the CTA train system is known as the 'El' (short for elevated) or the 'L' (short for El)! The Red and Blue lines go underground in the downtown area and might be referred to as a "subway" there, but in general the whole system is known as the 'El', so avoid calling it the subway. All the El lines radiate from downtown. The circle of downtown train tracks is called the "Loop" (which has become another name for the oldest section of downtown).
The El runs fairly late, though different lines run to different times, and some lines don't run their full length late at night. The Red and Blue lines run 24 hours a day. Single travelers should be advised that they may not feel safe late at night on the El.
The CTA services use fare cards called transit cards which you can keep topping up with money and reusing. Transit cards are sold and charged up from vending machines at El stations. The fare for the El and buses is $2.00 ($1.75 with a pre-paid "Chicago Card", which cannot be purchased at most stations). At certain El stations you can transfer to other train lines at no extra cost, as once you're inside the turnstiles, you can get on and off trains without paying again. Once you have exited the turnstiles, the first time you re-enter a turnstile or board a bus within 2 hours of starting the first trip, it costs $0.25 and the third transfer is free. The system automatically knows you are using the card for a transfer within the 2-hour period.
There are also visitor passes for unlimited travel. These are very convenient but fairly expensive and you'll probably save money by using normal fare cards. There's an attendant at every El station. They can't provide change or deal with money, but they can help you figure out where you need to go, or guide you through using the machines. The attendants are usually very bored and are happy to have something to do, so don't hesitate to ask them questions.
The cards and transfers work on the buses as well as the El, but cards are not sold on the buses. Buses also accept cash, but don't provide change, and if you want a transfer when paying cash you have to specifically ask (and pay) for the transfer.
Buses run on almost all the major streets in Chicago, and seldom run less frequently than every 30 minutes. The "major" streets are every 400 (400, 800, 1200, etc) in the numbering system, or every 1/2 mile. So you can get nearly anywhere with one transfer.
The El may be a source of ambivalence for most Chicagoans, but is most certainly a unique attraction in and of itself for visitors. To some, the short trip around the elevated Loop circuit may be worth every penny of the $2.00 fare. But you can also take a free Loop tour train with a guide from the Chicago Architecture Foundation - see the "Do" section below.
Downtown there are also free trolleys, used mostly by tourists. These are actually uncomfortable buses made to look like trolleys. They're a quick way to get around downtown. They use specially-marked bus stops, but they'll usually let you off wherever you want. They run every 20 to 30 minutes. Most run weekends only (Sa 10am-6pm, Su noon-6pm) except Jun-Aug when they also run M-F 10am-6pm. They also run weekdays at other holiday times. Navy Pier trolley now runs 7 days all year round during hours the pier is open. The official website has stops, times, and route maps.
If you travel by trolley, you might want an alternative for your return trip. The return trolleys may be full, late, not running at all, or you may just not want to get on them again (one trolley ride is enough for a lot of people). For alternatives you may want cab fare, a list of appropriate CTA routes and associated fares, or just walking directions.
By private car
Parking is expensive and not readily available in the center of the city, so public transit and taxis are recommended. Driving is quite recommended for suburbs without El service.
Good weather? Rent a bike from the North Avenue Beachhouse and pedal your way around the city. Chicago has many on-road bike lanes, park trails, and a scenic Lakefront Trail, which runs for 18 continuous miles along the city's beautiful shoreline. Bicycles can also be rented from several bike shops in the city. Chicago has a fine bicycle culture. Chicago is also completely flat - a boon for any bicycler!
Many streets have bike lanes on them, and the city has installed signs specifically pointing out directions to major bike routes . Bicyclists have to follow the same rules-of-the-road as autos; in some areas of the city, police officers write citations against bicyclists. On top of that, CTA buses area all equipped with bike racks to carry up to two bicycles, and CTA trains permit bicycles except during rush hour, which is roughly between 7:00 and 9:30 A.M. and 3:30 to 6:30 P.M.