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Search & Book American Airlines Flights to Chicago

American Airlines plane

Book American Airlines to & from Chicago

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 AffirmKlarna and more.

Use our search at the top of the page to search for flights to/from Chicago from anywhere in the world.

Picture of skyscrapers in Chicago

Flying with American Airlines to Chicago

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).

Where can I fly?

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.

US cities to Chicago

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.

Popular routes

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.

Canada to Chicago

American Airlines offers regular flights between destinations in Canada and Chicago, including Toronto, Montreal, Vancouver, Ottawa, Quebec City and more.

Popular routes

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.

Other International Flights to Chicago

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.

Popular routes

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.

All American Airlines Destinations to & from Chicago

Below is a table of all destinations that American Airlines connects with Chicago, plus which carrier operates that route.

ArubaArubaAmerican Airlines
CanadaCalgaryAmerican Eagle
CanadaMontréal–TrudeauAmerican Eagle
CanadaOntarioAmerican Airlines
CanadaQuébec CityAmerican Eagle
CanadaVancouverAmerican Airlines
Cayman IslandsGrand CaymanAmerican Airlines
CozumelCozumelAmerican Airlines
Dominican RepublicPunta CanaAmerican Airlines
FranceParis–Charles de GaulleAmerican Airlines
GreeceAthensAmerican Airlines
GuatemalaGuatemala CityAmerican Airlines
IrelandDublinAmerican Airlines
ItalyRome–FiumicinoAmerican Airlines
JamaicaMontego BayAmerican Airlines
MexicoCancúnAmerican Airlines
MexicoPuerto VallartaAmerican Airlines
MexicoSan José del CaboAmerican Airlines
Puerto RicoSan JuanAmerican Airlines
SpainBarcelonaAmerican Airlines
St.LuciaSt. Lucia–HewanorraAmerican Airlines
The BahamasNassauAmerican Airlines
Turks and Caicos IslandsProvidencialesAmerican Airlines
UKLondon–HeathrowAmerican Airlines
US Virgin IslandsSt. ThomasAmerican Airlines
USAAkron/CantonAmerican Eagle
USAAlbanyAmerican Eagle
USAAllentownAmerican Eagle
USAAnchorageAmerican Airlines
USAAppletonAmerican Eagle
USAAshevilleAmerican Eagle
USAAspenAmerican Eagle
USAAustinAmerican Airlines
USABangorAmerican Eagle
USABillingsAmerican Eagle
USABirmingham (AL)American Eagle
USABloomington/NormalAmerican Eagle
USABoiseAmerican Eagle
USABostonAmerican Airlines
USABuffaloAmerican Eagle
USABurlingtonAmerican Eagle
USACedar Rapids/Iowa CityAmerican Eagle
USAChampaign/UrbanaAmerican Eagle
USACharleston (SC)American Eagle
USACharlotteAmerican Airlines
USACharlottesvilleAmerican Eagle
USACincinnatiAmerican Eagle
USAClevelandAmerican Eagle
USAColorado SpringsAmerican Eagle
USAColumbia (MO)American Eagle
USAColumbus–GlennAmerican Eagle
USADallas/Fort WorthAmerican Airlines
USADaytonAmerican Eagle
USADenverAmerican Airlines
USADes MoinesAmerican Eagle
USADestin/Fort Walton BeachAmerican Eagle
USADetroitAmerican Eagle
USADubuqueAmerican Eagle
USAEagle/VailAmerican Airlines
USAEl PasoAmerican Eagle
USAErieAmerican Eagle
USAEvansvilleAmerican Eagle
USAFairbanksAmerican Airlines
USAFargoAmerican Eagle
USAFayetteville/BentonvilleAmerican Eagle
USAFlintAmerican Eagle
USAFort LauderdaleAmerican Airlines
USAFort MyersAmerican Airlines
USAFort WayneAmerican Eagle
USAFresnoAmerican Airlines
USAGlacier Park/KalispellAmerican Eagle
USAGrand RapidsAmerican Eagle
USAGreen BayGreen Bay
USAGreensboroAmerican Eagle
USAGreenville/SpartanburgAmerican Eagle
USAHarlingenAmerican Eagle
USAHarrisburgAmerican Eagle
USAHayden/Steamboat SpringsAmerican Airlines
USAHilton HeadAmerican Eagle
USAHonoluluAmerican Airlines
USAHouston–IntercontinentalAmerican Airlines
USAHuntsvilleAmerican Eagle
USAIndianapolisAmerican Eagle
USAJackson HoleAmerican Airlines
USAJacksonville (FL)American Eagle
USAJoplinAmerican Eagle
USAKalamazooAmerican Eagle
USAKansas CityBoth
USAKey WestAmerican Eagle
USAKnoxvilleAmerican Eagle
USALa CrosseAmerican Eagle
USALansingAmerican Eagle
USALas VegasAmerican Airlines
USALexingtonAmerican Eagle
USALittle RockAmerican Eagle
USALos AngelesAmerican Airlines
USALouisvilleAmerican Eagle
USAMadisonAmerican Eagle
USAManchester (NH)American Eagle
USAManhattan (KS)American Eagle
USAMarquetteAmerican Eagle
USAMemphisAmerican Eagle
USAMiamiAmerican Airlines
USAMilwaukeeAmerican Eagle
USAMinneapolis/St. PaulBoth
USAMissoulaAmerican Eagle
USAMoline/Quad CitiesAmerican Eagle
USAMontroseAmerican Eagle
USAMosinee/WausauAmerican Eagle
USAMyrtle BeachAmerican Eagle
USANantucketAmerican Eagle
USANashvilleAmerican Eagle
USANew OrleansAmerican Eagle
USANew York–JFKAmerican Airlines
USANew York–LaGuardiaAmerican Airlines
USANorfolkAmerican Eagle
USAOklahoma CityAmerican Eagle
USAOmahaAmerican Eagle
USAOrange County (CA)American Airlines
USAOrlandoAmerican Airlines
USAPalm SpringsAmerican Airlines
USAPanama City (FL)American Eagle
USAPensacolaAmerican Eagle
USAPeoriaAmerican Eagle
USAPhiladelphiaAmerican Airlines
USAPhoenix–Sky HarborAmerican Airlines
USAPortlandAmerican Eagle
USAPortland (OR)American Airlines
USAProvidenceAmerican Eagle
USARapid CityAmerican Eagle
USAReno/TahoeAmerican Airlines
USARichmondAmerican Eagle
USARochester (MN)American Eagle
USARochester (NY)American Eagle
USASacramentoAmerican Airlines
USASalt Lake CityBoth
USASan AntonioBoth
USASan DiegoAmerican Airlines
USASan FranciscoAmerican Airlines
USASan Jose (CA)American Airlines
USASanta BarbaraAmerican Airlines
USASarasotaAmerican Eagle
USASavannahAmerican Eagle
USASeattle/TacomaAmerican Airlines
USASioux CityAmerican Eagle
USASioux FallsAmerican Eagle
USASpokaneAmerican Airlines
USASpringfield/BransonAmerican Eagle
USASt. LouisBoth
USAState CollegeAmerican Eagle
USASyracuseAmerican Eagle
USATampaAmerican Airlines
USAToledoAmerican Eagle
USATraverse CityAmerican Eagle
USATucsonAmerican Airlines
USATulsaAmerican Eagle
USAWaterloo (IA)American Eagle
USAWest Palm BeachAmerican Airlines
USAWhite PlainsAmerican Eagle
USAWichitaAmerican Eagle
USAWilkes-Barre/ScrantonAmerican Eagle
USAWilmingtonAmerican Eagle

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What terminal does American Airlines fly to & from at Chicago O'Hare airport?

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.

Which planes do American Airlines use on its flights to & from Chicago?

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.

Where can I buy flights to Chicago with American Airlines?

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.

How do I buy flights to Chicago with American Airlines at Alternative Airlines?

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!

Can I fly direct from Madison to Chicago?

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.