Chicago ( for all airports) is served by two major airports: O'Hare International Airport and Midway Airport. There are plenty of taxis both to and from the city center, but they are quite expensive, especially during rush hours. Expect upwards of $40 for O'Hare and $30 for Midway. CTA trains provide direct service to both larger airports for $2.25 from anywhere in the city — faster than a taxi during rush hour and a lot less expensive. (Train rides originating at O'Hare are $5.)
Many large hotels offer complimentary shuttle vans to one or both airports, or can arrange one for a charge ($15–25) with advance notice.
O'Hare International Airport is 17 miles (27 km) northwest of downtown and serves many international and domestic carriers. United Airlines has the largest presence here (about 50%) followed by American Airlines with about 40%. Most connecting flights for smaller cities in the Midwest run through O'Hare. It's one of the biggest airports in the world, and it has always been notorious for delays and cancellations. Unfortunately, it's too far northwest for most travelers who get stuck overnight to head into the city. As a result, there are plenty of hotels in the O'Hare area. See the O'Hare article for listings.
The CTA Blue Line runs between the Loop and O'Hare at least every 15 minutes, 24 hours a day and 7 days a week. Many upgrades have recently been completed on the Blue line, and the trip from O'Hare to the Loop now takes 35–50 minutes. The O'Hare station is the end of the line and is essentially in the basement of O'Hare airport. Walking from the platform to the ticket counters should take 5–10 minutes for Terminals 2 or 3, slightly more for Terminal 1, and a great deal longer for the International Terminal 5 (It is necessary to take the free people mover for transfer).
Midway International Airport is 10 miles (16 km) southwest of downtown. Southwest Airlines is the largest carrier here, followed by AirTran. If it's an option for your trip, Midway is more compact, less crowded, has fewer delays, and usually cheaper. And, of course, it's significantly closer to downtown.
The CTA Orange Line train runs between the Loop and Midway in around 25 minutes. Keep in mind that the CTA Midway Station is at the end of the Orange Line. There is an enclosed tunnel that links the station and airport but it takes approximately 10–15 minutes to walk from one to the other. There are a number of hotels clustered around Midway, too — see the Southwest Side article for listings.
Chicago Executive Airport is nine miles north of O'Hare, serves the general and business aviation sector, and is the third busiest airport in Illinois. Approximately three hundred aircraft are based on the field and approximately 200,000 take-offs and landings occur annually. Air taxi and air charter companies such as Jetset Charter fly a variety of private charter aircraft and jets, from charter luxury Gulfstream's down to economical piston twins for small groups and individuals.
Milwaukee's General Mitchell International Airport is served by 7 Amtrak trains per day (6 on Sunday), and the Hiawatha Service has a 95% on-time rating. The trip from Chicago Union Station to Mitchell Airport Station is about one hour and 15 minutes. There are also buses from Mitchell Airport to Chicago O'Hare Airport.
Chicago is historically the rail hub of the entire United States. Today, Amtrak, ☎ +1 800 872-7245, uses the magisterial Union Station (Canal St and Jackson Blvd) as the hub of its Midwestern routes, making Chicago one of the most convenient U.S. cities to visit by train, serving the majority of the passenger rail company's long-distance routes, with options from virtually every major U.S. city. With its massive main hall, venerable history, and cinematic steps, Union Station is worth a visit even if you're not coming in by train.
Most (but not all) Metra suburban trains run from Union Station and nearby Ogilvie/Northwestern Station (Canal St and Madison St), which are west of the Loop. Some southern lines run from stations on the east side of the Loop. The suburban trains run as far as Kenosha, Aurora, and Joliet, while the South Shore line runs through Indiana as far as South Bend. Several CTA buses converge upon the two stations, and the Loop CTA trains are within walking distance.
Chicagoans have a maddening habit of referring to some expressways by their names, not the numbers used to identify them on the signs you'll see posted on the U.S. interstate highway system, so you'll have to commit both name and number to memory. I-55 (the Stevenson Expressway) will take you directly from St. Louis into downtown Chicago. I-90/94 (the Dan Ryan on the South Side) comes in from Indiana to the east (via the Chicago Skyway - I-90 and Bishop Ford Freeway - I-94) and from central Illinois (via I-57). I-90 (the Kennedy on the North Side) comes in from Madison to the northwest. I-94 (the Edens Expressway) comes in from Milwaukee to the north, but recent roadwork has slowed traffic considerably compared to I-90. I-80 will get you to the city from Iowa which neighbors Illinois to the west.
The Illinois tollway (which in addition to I-90 - The Jane Addams west of O'hare airport) consists of I-88 - The Reagan which serves the west suburbs, I-355 - The Veterans Memorial which connects Joliet with Schaumburg, and I-294 - The Tri-State which bypasses downtown from the south side to the far northwest side and passes next to O'hare airport. Be prepared for toll booths off to the right hand side of the tollway which will cost about $1.50 per booth. When travelling the tollways, always have a few dollars in cash to pay at the booths, which are staffed on mainline toll plazas, but not always at exits, so always have some coins as well. If you happen to be in the I-Pass lanes as you approach a tollbooth, do not cut across the expressway to get to the cash lanes, just go through. You have up to seven days to pay tolls online. Also, if you have an E-ZPass, it is fully compatible with the I-Pass system.
If arriving downtown from Indiana, from the south on I-94 or I-90, or from the north, Lake Shore Drive (U.S. Highway 41) provides a scenic introduction in both directions, day or night. If arriving on I-55 from the southwest, or on I-290 (the Eisenhower Expressway, formerly and sometimes still called The Congress Expressway) from the west, the skyline may also be visible from certain clear spots, but without the shore view. It should also be noted that I-55 from the southwest and I-90 through much of northwest Indiana are chock full of heavy industries with odors that'll knock your socks off, so plan your route downtown wisely.
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