Search and book American Airlines flights to and from Chicago with Alternative Airlines. We offer a fast, easy and convenient way to book American Airlines flights to and from the Windy City. When buying American Airlines flights with Alternative Airlines, you can pre-select your seat, add baggage and choose to pay with a range of different payment methods, including all major debit and credit cards, PayPal, as well as buy now pay later options such as Affirm, Klarna and more.
Use our search at the top of the page to search for flights to/from Chicago from anywhere in the world.
American Airlines flies to Chicago from all over the US and many other different cities in the world. Most international flights to and from Chicago are flown by American Airlines itself. Whereas, most of its domestic and Canadian flights to and from Chicago are flown by its regional brand, American Eagle.
Depending on whether you're flying domestic, international or even intercontinental, American Airlines will offer a slightly different set-up for your flight. Domestic flights have an Economy Class and First Class cabin. Flights to Canada have an Economy Class and Business Class cabin. Other short-haul international flights have an Economy Class, Business Class and First Class cabin. And, long-haul international flights have an Economy Class, Premium Economy, Business Class and First Class cabin. But, no matter where you're flying from or to, American Airlines flights to and from Chicago still give you the same great service that you'd expect from one of the US' most recognisable carriers.
American Airlines only flies to Chicago O'Hare International Airport (ORD) and doesn't fly to Chicago Midway Airport (MDW). So, when searching for flights to Chicago, make sure to select Chicago O'Hare (ORD).
American Airlines connects Chicago with destinations across the world, with hundreds of direct flights within the US, as well as international flights to Canada, Mexico, Central America and parts of Europe.
American Airlines connects Chicago with more than 100 destinations within the US. All American Airlines domestic flights to major cities are flown by American Airlines itself, whereas the flights to less in-demand regional destinations are flown by American Eagle.
Boston (BOS) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines
Miami (MIA) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines
Phoenix (PHX) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines
American Airlines offers regular flights between destinations in Canada and Chicago, including Toronto, Montreal, Vancouver, Ottawa, Quebec City and more.
Toronto (YYZ) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines & American Eagle
Vancouver (YVR) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines on a seasonal basis
American Airlines also connects Chicago with lots of other international destinations outside of the US and Canada. Including to Mexico, Aruba, Italy, France, the UK and more.
London (LHR) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines
Rome (FCO) ➡ Chicago O'Hare (ORD) — daily flights with American Airlines on a seasonal basis
Rome (FCO) ➡ Chicago O'Hare (ORD) — 1 x weekly flights with American Airlines on a seasonal basis
Below is a table of all destinations that American Airlines connects with Chicago, plus which carrier operates that route.
|COUNTRY||CITY||American Airlines/American Eagle|
|Québec City||American Eagle|
|Cayman Islands||Grand Cayman||American Airlines|
|Dominican Republic||Punta Cana||American Airlines|
|France||Paris–Charles de Gaulle||American Airlines|
|Guatemala||Guatemala City||American Airlines|
|Jamaica||Montego Bay||American Airlines|
|Puerto Vallarta||American Airlines|
|San José del Cabo||American Airlines|
|Puerto Rico||San Juan||American Airlines|
|St.Lucia||St. Lucia–Hewanorra||American Airlines|
|The Bahamas||Nassau||American Airlines|
|Turks and Caicos Islands||Providenciales||American Airlines|
|US Virgin Islands||St. Thomas||American Airlines|
|Birmingham (AL)||American Eagle|
|Cedar Rapids/Iowa City||American Eagle|
|Charleston (SC)||American Eagle|
|Colorado Springs||American Eagle|
|Columbia (MO)||American Eagle|
|Dallas/Fort Worth||American Airlines|
|Des Moines||American Eagle|
|Destin/Fort Walton Beach||American Eagle|
|El Paso||American Eagle|
|Fort Lauderdale||American Airlines|
|Fort Myers||American Airlines|
|Fort Wayne||American Eagle|
|Glacier Park/Kalispell||American Eagle|
|Grand Rapids||American Eagle|
|Green Bay||Green Bay|
|Hayden/Steamboat Springs||American Airlines|
|Hilton Head||American Eagle|
|Jackson Hole||American Airlines|
|Jacksonville (FL)||American Eagle|
|Key West||American Eagle|
|La Crosse||American Eagle|
|Las Vegas||American Airlines|
|Little Rock||American Eagle|
|Los Angeles||American Airlines|
|Manchester (NH)||American Eagle|
|Manhattan (KS)||American Eagle|
|Moline/Quad Cities||American Eagle|
|Myrtle Beach||American Eagle|
|New Orleans||American Eagle|
|New York–JFK||American Airlines|
|New York–LaGuardia||American Airlines|
|Oklahoma City||American Eagle|
|Orange County (CA)||American Airlines|
|Palm Springs||American Airlines|
|Panama City (FL)||American Eagle|
|Phoenix–Sky Harbor||American Airlines|
|Portland (OR)||American Airlines|
|Rapid City||American Eagle|
|Rochester (MN)||American Eagle|
|Rochester (NY)||American Eagle|
|Salt Lake City||Both|
|San Diego||American Airlines|
|San Francisco||American Airlines|
|San Jose (CA)||American Airlines|
|Santa Barbara||American Airlines|
|Sioux City||American Eagle|
|Sioux Falls||American Eagle|
|State College||American Eagle|
|Traverse City||American Eagle|
|Waterloo (IA)||American Eagle|
|West Palm Beach||American Airlines|
|White Plains||American Eagle|
The majority of American Airlines and American Eagle flights depart and arrive at Terminal 3 at Chicago O'Hare International Airport, regardless of where it's flying to or has come from. The airline also uses Terminal 5 for some flights.
This can be subject to change for any given flight, so it's always important to check which terminal your individual flight is departing or arriving to.
This will differ depending on where your flight is flying to and from. On regional flights, a lot of the time, American Eagle uses the Embraer E-Jet or ERJ family or Bombardier CRJ-700. On flights operated by American Airlines, the airline use planes from the Airbus A320 family and Boeing 737 family for short-haul flights and Boeing 777 and 787 for long-haul flights.
If you want to know what plane is going to be used for your flight before you buy it, you can check this in our flight search results once you've found the flight that you're interested in purchasing on the Alternative Airlines website.
You can buy flights to Chicago with American Airlines right here on the Alternative Airlines website. We sell all flights travelling to and from Chicago on American Airlines and allow you to pre-select your seat and add baggage on any American Airlines flight.
Plus, we offer more than 25 ways to pay for your flights, including PayPal, all major debit and credit cards, as well as financing options and even cryptocurrencies.
To buy flights to and from Chicago with American Airlines, use our flight search at the top of the page. All you need to do is enter Chicago (ORD) and the other destination that you want to fly between, select your dates and hit search flights.
In a few seconds, we'll show you all available flights for your chosen dates and route. You can use our handy filters to select to view only American Airlines flights, which will make it super-easy to find the flight that you want.
Once you've found the flight, select it to confirm. After that, you'll just need to enter your passenger details and confirm your flight with payment. Once payment is complete, we'll send you your e-ticket right away!
Yes! Flights to Chicago from Madison, Wisconsin, are available daily. You can book direct flights from Madison to Chicago right here at Alternative Airlines. Airlines that operate this route include American Eagle, United Airlines and United Express.