The reasons to want to fly to Chicago are manifold. You might want a city break filled with world-renowned art and architecture. Perhaps it's a weekend of fine dining and retail therapy on the Magnificent Mile. Maybe you and your buddies have tickets for a game — be it the Blackhawks, Bulls, Cubs, White Sox, or even the Fire. Or you could be in town on business to do some wheeling and dealing or attend a convention. There are tons of attractions that draw visitors to Chicago year-round, from the well-known such as Millennium Park and Navy Pier, to the unexpected such as the Oriental Institute Museum or fishing on Lake Michigan.
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Chicago's O'Hare International Airport (ORD) is one of the busiest airports in America, serving international airlines from all over the world, including Air Canada, American Airlines, American Eagle, British Airways, Continental, Delta, JetBlue, Spirit Airlines, United, US Airways, and Virgin America. Midway International Airport (MDW) is no slouch either, acting as a major hub for low-cost carrier Southwest Airlines and domestic flights for other carriers such as AirTran, Delta Airlines, and Frontier. Consequently, cheap flights to Chicago are usually plentiful throughout the year.
Chicago is an enormously popular city for conferences and events, so it is worthwhile to do some preliminary research about what events are planned before setting the dates for your trip and booking a ticket. Accommodations can be scarce and more expensive when several major events are happening in the city at once. July and September can be especially challenging in this regard.
As with most North American destinations, Chicago is nicest in the summertime (June through September) which, consequently, is the high season for travel. The winter months are cold, but that's when you'll find the best deals on flights and hotels. If your interests are mainly indoor activities such as museums, dining, or shopping, January through March can be an excellent time to fly to Chicago —you'll need to bundle up but you'll also save a bundle. Attractions in Chicago are open throughout the year, making it a great place to travel to even in the cheap off-season.
Your flight to Chicago will land at either O'Hare International Airport (ORD) or Midway Airport (MDW), and there are several modes of ground transportation that will take you from the airport to Chicago's city centre.
Arriving at O'Hare
O'Hare has four terminals in use serving flights to and from destinations all over the world, so it is important to pay attention to the terminals listed on your airline ticket if you are catching a connecting flight, and allow time to transfer between terminals if necessary.
Public Transit: This is by far the cheapest ground transportation option, costing around $2 from O'Hare to downtown Chicago. There is an 'L" train station right at the airport which is less than a 10-minute walk from the baggage claim areas in Terminals 1,2, or 3 –simply follow the signs. From Terminal 5, take the Airport Transit System to Terminal 2, and then follow the signs to the 'L' station, which is on the Blue Line. The train to downtown takes approximately 45 minutes.
Taxi: Once your flight lands, cabs are readily available from the Arrivals area of each terminal. Taxi fare from O'Hare to downtown will be around $40 and can take up to 90 minutes depending on traffic.
Airport Shuttle: GO Airport Express offers shuttle service from O'Hare to downtown Chicago starting at $25 per person each way. Ticket counters can be found in the baggage claim area of each terminal, where you can buy your shuttle ticket if you haven't already booked online, or made a reservation by phone. The attendant will summon a shuttle for you if one is not already waiting. Shuttles depart approximately every 10-15 minutes until 11:30 p.m. and can take up to 90 minutes to reach your destination depending on the traffic. Check their website for discounts and special offers. OMEGA Airport Shuttle offers transportation between O'Hare and Midway airports, as well as service to the South Side from O'Hare, for approximately $35.
Hotel Shuttle: Some hotels offer complimentary shuttle service to and from O'Hare airport, especially those near the airport. It's worth checking with the hotel you've booked whether they offer a courtesy shuttle. If so, proceed to the Shuttle Bus Center after disembarking from your flight to Chicago, where all of the hotel shuttles pick up and drop off passengers.
Car Rental: While driving in Chicago is not necessarily advisable due to a myriad of factors including congestion and the prevalence of tolls, it is possible to rent a car at O'Hare airport. Car rental counters are located in the Lower Level Roadway near the Arrivals area.
Arriving at Midway
Midway is primarily a domestic airport, although it does offer flights between Toronto and Chicago via Porter, so you might find yourself landing there if you book a ticket on this route. The airport has one terminal which is divided into three concourses. International arrivals go through Concourse A. Concourse B is dedicated to Southwest Airlines, and Concourse C is exclusively for Delta Airlines and its connections.
Public Transit: Midway is on the Orange Line of the 'L' Train and it takes approximately 25 minutes to travel downtown. The fare is around $2 per ticket, depending on if you qualify for discounts such as those for seniors and youth. This is definitely the cheapest option.
Taxi: Taxicabs are available at Midway airport. Simply follow the signs in the Arrivals area to the taxi stand. The fare may not be cheap, but a cab will take you anywhere you want to go.
Airport Shuttle: GO Airport Express offers shuttle service from Midway. The ticket counter and loading zone are located at Door 3 near the baggage claim in the Arrivals area, and shuttles depart approximately every 15 minutes until 11:30 p.m. Discounts can be obtained by booking in advance online.
Hotel Shuttle: Some Chicago hotels, particularly those near the airport, have courtesy shuttles that will take you to and from the airport for free. It's worth checking whether your accommodation in Chicago includes this amenity.
Car Rental: Cars can be rented from several companies at Midway airport, including Avis and Budget. Follow the signs in the Arrivals area.