To Chicago: from New York, 2 hours; from Dallas, 2½ hours; from San Francisco, 4 hours; from Los Angeles, 4 hours; from London, 7 hours; from Sydney, 17 hours (not including layovers).
In Chicago the general rule is to arrive at the airport two hours before an international flight; for a domestic flight, plan to arrive 90 minutes early if you're checking luggage and 60 minutes if you're not.
Airline Security Issues
Transportation Security Administration. The TSA has answers for almost every question that might come up. 866/289–9673; www.tsa.gov.
The major gateway to Chicago is O'Hare International Airport (ORD). Because it’s one of the world's busiest airports, all major airlines pass through here. The sprawling structure is 19 miles from downtown, in the far northwest corner of the city. It can take anywhere from 30 to 90 minutes to travel between downtown and O'Hare, based on time of day, weather conditions, and construction on the Kennedy Expressway (Interstate 90). The Blue Line El train offers a reliable 45-minute trip between the Loop and O'Hare.
Got some time to spend before your flight? Plenty of dining and shopping options are scattered throughout O'Hare's four terminals. Chicago favorites such as the Berghoff Café, Billy Goat Tavern, Goose Island Brewing Company, Pizzeria Uno, Garrett Popcorn, and Chef Rick Bayless's Tortas Frontera can be found among the usual chain restaurants. Grab that last-minute souvenir or in-flight necessity at an array of shops, including the Field Museum Gift Shop and Vosges Haut-Chocolat. Take young travelers to visit the Chicago Children's Museum's "Kids on the Fly" exhibit. Or spring for a mini-massage from the Back Rub Hub. Wi-Fi is also available throughout the complex.
If you're stuck at O'Hare longer than you expected, the Hilton Chicago O'Hare (773/686–8000) is within walking distance of all terminals.
Midway Airport (MDW) is about 11 miles southwest of downtown; it's served by Southwest, Delta, AirTran, and Frontier. Driving between Midway and downtown can take 30 to 60 minutes, depending on traffic conditions on the Stevenson Expressway (Interstate 55). The Orange Line El train runs from the Loop to Midway in about 30 minutes.
Some say the more recently renovated Midway has better dining options than O'Hare. With downtown standouts such as Harry Caray's, Manny's Deli, Pegasus On the Fly, and Lalo's Mexican Restaurant all on-site, it's a good point. The Midway Boulevard area in the center of the building features cute shops such as Discover Chicago and Kids Works. Wi-Fi is available throughout the airport.
An extended stay near Midway Airport can be spent at a number of nearby hotels, including the Chicago Marriott Midway (800/228–9290), Hampton Inn Midway (708/496–1900), and Hilton Garden Inn Midway (708/496–2700).
Security screenings at both airports can be fairly quick during off-peak travel times or long and arduous during the holidays.
Long layovers don't have to be only about sitting around or shopping. These days they can be about burning off vacation calories. Check out www.airportgyms.com for lists of health clubs in or near many U.S. and Canadian airports.
Chicago Midway Airport. 773/838–0600; www.flychicago.com/midway/en/home/Pages/default.aspx.
O'Hare International Airport. 773/686–2200; 800/832–6352; www.flychicago.com/ohare/en/home/Pages/default.aspx.
If you're traveling to or from either airport by bus or car during morning or afternoon rush hours, factor in some extra time—ground transport can be slow.
Shuttle buses run between O'Hare and Midway airports and to and from either airport and various points in the city. When taking an airport shuttle bus to O'Hare or Midway to catch a departing flight, be sure to allow at least 1½ hours. When going to either airport, it's a good idea to make a reservation 24 hours in advance. Though some shuttles make regular stops at the major hotels and don't require reservations, it's best to check. Reservations are not necessary from the airports. Omega Airport Shuttle offers hourly service between the two airports for approximately $45 per person; travel time is approximately one hour. The company also provides an hourly service from the two airports and Hyde Park. The fare is $35 from O'Hare to Hyde Park and $19 from Midway to Hyde Park. GO Airport Express coaches provide service from both airports to major downtown and Near North locations as well as to most suburbs. The ride downtown from O'Hare takes at least 45 minutes, depending on traffic conditions, and the fare is $30, $54 round-trip; the ride downtown from Midway takes at least a half hour and the fare is $25, $44 round-trip. Call to find out times and prices for other destinations.
Depending on traffic and the time of day, driving to and from O'Hare takes about an hour, and driving to and from Midway takes at least 45 minutes. From O'Hare, follow the signs to Interstate 90 east (Kennedy Expressway), which merges with Interstate 94 (Edens Expressway). Take the eastbound exit at Ohio Street for Near North locations, the Washington or Monroe Street exit for downtown. After you exit, continue east about a mile to get to Michigan Avenue. From Midway, follow the signs to Interstate 55 east, which leads to Interstate 90.
Metered cab service is available at both O'Hare and Midway airports. Trips to and from O'Hare may incur a $1 surcharge to compensate for changing fuel costs. Expect to pay about $40 to $45 plus tip from O'Hare to Near North and downtown locations, about $30 to $35 plus tip from Midway. Some cabs, such as Checker Taxi and Yellow Cab, participate in a shared-ride program in which each car carries up to four individual passengers going from the airport to downtown. The cost per person—a flat fee that varies according to destination—is substantially lower than the full rate.
Chicago Transit Authority (CTA) trains, called elevated or El trains, are the cheapest way to and from the airports; they can also be the most convenient transfer. "Trains to city" signs will guide you to the subway or elevated train line. In O'Hare Airport the Blue Line station is in the underground concourse between terminals. Travel time to the city is about 45 minutes. Get off at the station closest to your hotel; or disembark at the first stop in the Loop (Clark and Lake streets), and then take a taxi to your hotel or change to other transit lines. At Midway Airport the Orange Line El runs to the Loop. The stop at Adams Street and Wabash Avenue is the closest to the hotels on South Michigan Avenue; for others, the simplest strategy is to get off anywhere in the Loop and hail a cab to your final destination. Train fare is $2.25, and you'll need to pay by transit card. Transit card vending machines are in every train station. They do not give change, so add only as much as you'd like to put on your card. Pick up train brochures and system maps outside the entrances to the platforms; the CTA's "Transit Stop" app is also helpful.
Transfers Between Airports
O'Hare and Midway airports are on opposite ends of the city, so moving between them can be an arduous, time-consuming task. Your best and cheapest move is hopping on the El. You will travel the Blue Line to the Orange Line, transferring at the Clark/Lake stop to get from O'Hare to Midway, reversing the trip to go from Midway to O'Hare. The entire journey should take you less than two hours.
Taxis and Shuttles
American United Cab Co. 773/248–7600; americanunitedtaxiaffiliation.com.
Checker Taxi. 312/243–2537; www.checkertaxichicago.com.
Flash Cab. 773/561–4444; www.flashcab.com.
GO Airport Express. 888/284–3826; www.airportexpress.com.
Omega Airport Shuttle. 773/734–6688; www.omegashuttle.com.
Yellow Cab. 312/829–4222; www.yellowcabchicago.com.
Public Transit Information
CTA. 888/968–7282; www.transitchicago.com.