Chicago O’Hare International Airport (ORD)

Airport Transit System runs between all terminals and the Car Rental Center and the commuter train airport station every 8 minutes.

Car Rentals: Alamo, Avis, Budget, Dollar, Hertz, and National provide 24/7 counter service in the baggage claim area and shuttle buses to their car lots.  A trip downtown via the Dan Ryan Expressway takes between 40 to 70 minutes—traffic dependant.

Taxis run 24/7 at the airport and major downtown hotels, including Yellow Cab (312-829-4222) and Checker (312-243-2537. Some taxis take multiple passengers from the airport to separate downtown locations.  Confirm your arrangement before leaving. Shuttle: Continental Air Transport (312-454-7800) runs a shuttle bus from ORD to dozens of downtown hotels for about $20 from 6a-11:30p.

Midway Airport (MDW)

Car Rentals: Alamo, Avis, Budget, Dollar, Hertz, and National provide 24/7 car rental counter service and shuttle buses to their car lots. Turn your car radio to 800 AM for airport traffic news.

Taxis:  Catch them outside the main terminal (Yellow 312-829-4222 and Checker 312-243-2537).  Taxis rides downtown take between 25 to 50 minutes. Shuttle: Continental Air Transport (312-454-7800) runs a shuttle bus from MDW to downtown hotels for about $16 from 6 am-10 pm. 

Here are several dependable, low cost ways to/from the airports and downtown:

Chicago Transit Authority runs a 24-hour subway line from ORD to the Loop that completes the journey in 40 minutes.
Chicago Transit Authority also runs a frequent subway line from MDW to the Loop. 
Metra North Central commuter train runs between ORD and Union Station downtown Monday-Friday. Board at Parking Lot F in the airport, where a free shuttle takes you to the Airport Transit System.

A Beaux Arts-style building with soaring Corinthian columns, terracotta walls, a pink marble floor crowned with a barrel-vaulted atrium ceiling, Union Station is located at West Adams & South Canal Street, just west of downtown. Union Station hosts these train routes:

Amtrak Hiawatha: Milwaukee-Chicago
Amtrak California Zephyr: Chicago-Omaha-Denver-Salt Lake City-Reno-Oakland
Amtrak City of New Orleans: Chicago-Carbondale-Memphis-Jackson-New Orleans
Amtrak Empire Builder: Chicago-Milwaukee-Minneapolis-Spokane-Seattle/Portland
Amtrak Cardinal: NYC-Philadelphia-Baltimore-DC-Cincinnati-Indy-Chicago
Amtrak Michigan: Chicago-Kalamazoo-Detroit-Pontiac & Chicago-Grand Rapids
Amtrak Missouri: Chicago-Springfield-St Louis-Jefferson City-Kansas City
Amtrak Illinois: Chicago-Quincy and Chicago-St Louis and Chicago-Carbondale
Amtrak Capitol Limited: DC-Pittsburgh-Cleveland-Toledo-Chicago
Amtrak Southwest Chief: Chicago-Kansas City-Albuquerque-Flagstaff-Los Angeles
Amtrak Texas Eagle: Chicago-St. Louis-Little Rock-Dallas-Ft Worth-San Antonio

Given the success of the Hiawatha route with Chicago as the hub, Amtrak routes connecting Minneapolis, Milwaukee, St. Louis, Detroit, Indianapolis, Kansas City, Cincinnati, Louisville, Omaha and Cleveland are being incrementally upgraded each year to become a Midwest High Speed Rail network by ~2016. To capitalize on that increasing train demand, Union Station is being redeveloped with 80,000 square feet of retail space, 600,000 square feet of office space and a 320-room business-class hotel.

Chicago Transit Authority (CTA) is one of the nation’s most extensive rail transit systems with over 222 miles, 143 stations and 7 rail lines. Heavily patronized, nearly 500,000 passengers ride daily from 5a–12p. The CTA provides downloadable maps and schedules for these lines:

Purple Line – Northside to Downtown
Red Line – Northside to Downtown to Southside
Blue Line – O’Hare Airport to Downtown to Westside
Brown Line – Northwest to Downtown
Green Line – Westside to Downtown to Southside
Orange Line – Midway Airport (Southwest) to Downtown
Yellow Line – Skokie to Northside

Both airport lines provide good aerial views of the city. Its most beloved line is the “L”, which circles the Loop business, government and cultural district downtown. All lines run frequently on weekdays. Some lines run light service during weekends and holidays. Single travelers are advised to only use the CTA during the daytime, except for the two airport lines, which are well-patronized day or night.  Excluding the airports, cost is about $1.50 to ride throughout the system. Check with the station attendant regarding passes for ages 7-11 to ride at a reduced fare and ages 6 and younger to ride FREE.

Metra commuter trains comprise an additional 495-mile system with 230 stations in Cook, Du Page, Lake, Will, McHenry and Kane counties via 12 rail lines. You can even purchase tickets over the Internet. Although several lines service the Southside (Electric, Rock Island, South Shore), Metra is primarily a benefit to suburban commuters from all points north, northwest, west, southwest, south and southeast to downtown. Trains travel from 50-79 mph and one-way fares vary from $1.75 to $6.60—zone dependant. On weekends and holidays, youngsters 12-17 ride for half fare. Plus, family fares allow kids under 12 to ride free when accompanied by a fare-paying adult. The main Metra terminal at Michigan Ave and Randolph Streets has an overhead park and gardens in the northwest corner of Grant Park.

Chicago Freeway and Tollway Network is logical, extensive and signage is adequate. Though you have periods of fast moving traffic, count on slow traffic between O’Hare and downtown during commute hours and event weekends, downtown. The two passenger car pool lanes are a big plus. Other freeways are only crowded during commute hours. All tollways are in the western suburbs or the Chicago Skyway going to Gary, Indiana. The tollways, expressways and major highways are:

  41 Lake Shore Drive
  55 Adlai Stevenson Expressway
  57 Dan Ryan Expressway
  80 Tri-State Expressway
  88 East-West Tollway
  90 Chicago Skyway/JFK Expressway/Northwest Tollway
  94 Dan Ryan Expressway/ JFK Expressway/Edens Expressway
290 Dwight Eisenhower Expressway
294 Tri-State Tollway
912 East Chicago-Gary Expressway