Chicago runs on two airports, and they couldn't be more different. O'Hare International (ORD) is a global mega-hub that handled 857,392 aircraft operations in 2025 — a takeoff or landing every 37 seconds — while Midway (MDW), just 20 minutes southwest of downtown, moves a much smaller but still impressive 19.4 million passengers a year. Together, the pair served more than 104 million travellers across roughly 290 destinations last year.

O'Hare is the heavyweight. It covers over 7,200 acres, runs eight runways (the longest stretching 13,000 feet), and offers about 1,000 daily direct flights to more than 190 US cities plus 120 daily flights to over 70 international destinations across 48 airlines. United and American dominate here, holding 99 and 66 of the airport's 165 gates respectively — a reminder that ORD is primarily a connecting hub, not just a place to start or end a trip. The facility also claims a $70 billion annual economic impact and ranks as the sixth busiest airport in the world.

Midway is the compact, low-fuss option. It sits on just 775 acres with three concourses and 43 gates, and it's essentially a Southwest Airlines fortress — the carrier uses it as its Midwest hub with around 200 daily departures to 80 US cities. International service is thin but leisure-focused: Cancun was the top foreign destination with about 134,000 passengers, and Southwest, Frontier and Volaris connect Chicagoans to Punta Cana, Montego Bay, Guadalajara, Morelia and other sunny spots.

Both airports are in the middle of serious construction. O'Hare's ORDNext programme includes the $1.45 billion New Concourse D, started in August 2025 and due in 2028, adding 19 gates that can all process international arrivals through US Customs. Midway is getting a $184 million Central Terminal Pad for aircraft staging and deicing, expected in early 2029, plus a $27 million taxiway pavement rehabilitation wrapping up in mid-2027.

For travellers, the choice is simple in practice. Flying long-haul, connecting through a hub, or crossing an ocean? You'll almost certainly be at O'Hare, which is far from the city centre but reachable via the CTA Blue Line. Booking a Southwest or Frontier domestic fare or a cheap beach getaway? Midway's smaller size means shorter walks and quicker exits, and the Orange Line runs straight to the Loop. Just note that when it comes to getting around, budget extra time at O'Hare — with four terminals and 11 concourses, it's a genuine airport to navigate rather than a quick in-and-out.