How we know: Sources are listed at the end. Airport and route facts come from the cited references. Live fares are on the linked route pages.
For most international trips from Chicago the answer is O'Hare, and it is not close. Midway is worth knowing about for a specific set of Mexico, Caribbean and Canada routes and for positioning on Southwest.
O'Hare: the global airport
O'Hare handled about 84.9 million passengers in 2025 and is a hub for both United and American (O'Hare International Airport). Between the two hubs and the foreign carriers, it has nonstops to Europe, Asia, the Middle East, Latin America and Canada: Air France to Paris, ANA to both Tokyo airports, Aer Lingus to Dublin, Air Canada to Montréal, Toronto and Vancouver, and American alone to London, Mexico City and more than forty other international destinations (O'Hare International Airport). See Chicago to Tokyo, Chicago to London and Chicago to Paris.
Terminal 5 houses US Customs and Border Protection and most foreign-carrier departures; it is separated from Terminals 1–3 by taxiways with no walkway, so connections between it and the domestic terminals use the Airport Transit System (O'Hare International Airport). United's and American's own international flights mostly depart from their domestic terminals and arrive at T5.
Midway: Southwest's airport
Midway served about 22 million passengers in 2023 and Southwest carries more than 90% of them (Midway International Airport). Its international map is short but useful: Southwest to Cancún, Punta Cana and Montego Bay; Volaris to Guadalajara, Morelia, Aguascalientes, Durango, León, San Luis Potosí and Zacatecas; and Porter to Toronto's downtown Billy Bishop airport (Midway International Airport). See Midway to Cancún.
When Midway is the better choice
- Your destination is on that list, especially Cancún, Punta Cana or Montego Bay, where Southwest's bags-included fares compare well once you add bag fees to a low-cost O'Hare fare.
- You are flying to interior Mexico (Guadalajara, León, Morelia) where Volaris has nonstops O'Hare does not.
- You want downtown Toronto rather than Pearson.
- You are positioning to another Southwest city for a long-haul from there.
Getting there from the Loop
Both airports have CTA rail: the Blue Line to O'Hare runs 24 hours with direct service into the Loop subway, and the Orange Line to Midway takes roughly 20–25 minutes to downtown (Midway International Airport). Midway is closer to the South Side and the Loop by road; O'Hare is closer to the northern suburbs. The Kennedy Expressway to O'Hare is unreliable at peak; the Blue Line is the safer bet for an evening long-haul departure.
Our recommendation by trip type
- Europe, Asia, Middle East, South America: O'Hare, no real alternative.
- Cancún, Punta Cana, Montego Bay: price both; Midway on Southwest is often competitive with bags included.
- Interior Mexico: Midway on Volaris, or O'Hare on Aeroméxico/American to Mexico City and connect.
- Toronto: Midway–Billy Bishop if downtown is the goal; O'Hare–Pearson for onward connections.
For timing, anchor to today's fare on the route page and set a price alert; leisure routes from both airports peak at spring break and Christmas.
FAQ
Does Midway have international flights? Yes: Southwest to Cancún, Punta Cana and Montego Bay, Volaris to several Mexican cities, and Porter to Toronto.
Which terminal at O'Hare is international? Terminal 5 for most foreign carriers and all international arrivals; United and American international departures mostly leave from their domestic terminals.
Is Midway cheaper than O'Hare? For its handful of international routes it can be, especially once bags are counted. For everywhere else it does not fly.