We track over 140 international routes from O'Hare daily, and exactly three from Midway — all to Mexico on Southwest. If you're flying outside North America, this isn't even a debate: ORD handles 97% of Chicago's international departures, and Midway exists almost entirely for domestic Southwest connections.
Why O'Hare Dominates International Routes From Chicago
O'Hare operates five terminals, with Terminal 5 dedicated entirely to international flights. Our monitoring data shows ORD averages 82 daily long-haul international departures across carriers like United, American, British Airways, Lufthansa, Air France, and every major Middle Eastern and Asian carrier. Midway, by contrast, sees seasonal service to Cancun, Puerto Vallarta, and Cabo — routes that Southwest prices more like domestic flights than true international fares.
The infrastructure gap is massive. O'Hare has U.S. Customs and Border Protection processing for 12,000+ arriving international passengers per hour. Midway's limited international capacity means even its Mexico flights require tight customs coordination. When we compare transatlantic fares, ORD to London routes consistently price 15-30% below connecting through Midway on Southwest with a layover in Denver or Phoenix.
For context on how O'Hare stacks up nationally, check our breakdown of the cheapest U.S. airports for international flights — ORD ranks in the top tier for both route diversity and competitive pricing on Europe and Asia routes.
What International Travelers Find at O'Hare's Terminal 5
Terminal 5 at ORD is where all your international options live. United operates the majority of flights here, with service to 45+ international cities on their own metal, plus Star Alliance partners like Lufthansa, Swiss, Austrian, and ANA. American uses Terminal 3 for most domestic connections but routes Oneworld international partners through Terminal 5 as well.
From our monitoring: Tokyo flights from ORD average $780 roundtrip in shoulder season (April-May, September-October), running on United, ANA, and Japan Airlines. Paris routes run $520-$680 on American, United, and Air France depending on season. We've tracked ORD-Frankfurt as low as $472 roundtrip on Lufthansa during January flash sales.
The terminal consolidation matters for tight connections. If you're arriving from Madison or Grand Rapids on a United regional jet and connecting to an international flight, you're likely already in Terminal 1 or 2 — a free ATS train ride to Terminal 5 with no TSA re-screening required. Midway offers no equivalent international connectivity infrastructure.
The Rare Case for Midway: When Southwest Positioning Beats Direct
Midway makes sense in exactly one scenario: when a Southwest transcontinental fare plus positioning flight undercuts a direct ORD international ticket by $200+, and you have status for free checked bags. We see this maybe 4-6 times per year on our Chicago departure hub alerts.
Example from our monitoring: Last November, Southwest ran $89 one-way MDW-LAX fares during a sale, while ORD-LAX on United/American sat at $240. If you were connecting in LA to an international flight on a partner airline, the Midway route saved $150 each way — enough to justify the extra complexity of separate tickets and the risk of missing your connection.
But this strategy only works if you're comfortable with:
- Booking separate tickets with no protection if Southwest delays
- Leaving 4+ hours between your MDW arrival and international departure from another city
- Checking bags twice if your Southwest flight and international carrier aren't through-ticketed
For 95% of international trips from Chicago, this math doesn't pencil out. Direct ORD departures win on time, convenience, and often price once you factor in positioning costs.
Routes You Can Only Fly Direct From O'Hare
ORD is the sole Chicago gateway for hundreds of city pairs. From our current monitoring, these routes have zero Midway equivalent, even connecting:
Asia-Pacific: Tokyo (United, ANA, JAL), Seoul (United, Korean, Asiana), Beijing (United, Air China), Shanghai (United, China Eastern), Hong Kong (Cathay Pacific), Delhi (United, Air India), Mumbai (Air India), Tel Aviv (United, El Al)
Europe: London (United, American, British Airways, Virgin Atlantic), Paris (United, American, Air France), Frankfurt (United, Lufthansa), Munich (United, Lufthansa), Zurich (United, Swiss), Amsterdam (United, KLM), Dublin (United, Aer Lingus), Madrid (United, Iberia), Rome (United, ITA), Athens (United)
Middle East: Doha (Qatar), Dubai (Emirates), Abu Dhabi (Etihad)
Latin America: São Paulo (United, LATAM), Buenos Aires (United, Aerolíneas Argentinas), Lima (United, LATAM), Bogotá (United, Avianca, Copa via Panama)
Midway's Mexico service covers leisure destinations that see heavy competition from ORD as well — often at similar or lower prices on full-service carriers with better schedules. When Southwest runs $240 roundtrip MDW-Cancun, we typically see United or American at $260-$280 from ORD with more departure time options and through-checked bags to your resort.
Set a price alert for your specific international route to see when ORD sales drop below Southwest's best MDW positioning fares.
Getting There: CTA Blue Line vs Orange Line Trade-Offs
Transit access favors different neighborhoods depending on where in Chicago you live. The CTA Blue Line runs 24/7 from downtown and near west side neighborhoods to O'Hare in 40-45 minutes for $5. The Orange Line connects the Loop to Midway in 25-30 minutes, also $5, but doesn't run overnight (roughly 4am-11:30pm daily).
From our informal surveys of Wildly users in Chicago: Blue Line reliability to ORD has improved significantly since 2023 track work completed, with 85-90% of trains running within 5 minutes of schedule during peak hours. Orange Line to Midway runs more consistently but serves fewer neighborhoods directly.
Rideshare economics: An Uber or Lyft from River North to O'Hare averages $35-$45 without surge pricing, typically 25-35 minutes in non-rush traffic. The same ride to Midway costs $28-$38, running 20-30 minutes. The price difference shrinks to $5-$7 in most cases — not enough to offset the international route disadvantage at MDW.
If you live south or southwest of the Loop (Pilsen, Bridgeport, Beverly), Midway's location saves 15-20 minutes of travel time. But you're still limited to those three Mexico routes unless you're connecting onward via Southwest, which adds back all the time you saved and then some.
Our Recommendation By Trip Type
Traveling to Europe, Asia, Middle East, or South America: Use O'Hare. This isn't negotiable. Midway has no service to these regions, and connecting through Southwest hubs adds 4-8 hours of travel time plus separate ticket risk. ORD's direct routes and alliance connectivity make it the only viable option. For best prices, check our guide to finding cheap flights, which covers the booking windows when ORD transatlantic and transpacific fares drop hardest.
Mexico beach destinations: Compare both airports, but expect ORD to win on schedule flexibility and usually price. From our monitoring, Southwest's MDW-Mexico fares rarely beat ORD's full-service carriers by more than $40-60 roundtrip, and United/American often include seat selection and checked bags at price points where Southwest charges extra for both. Set another alert if you want both airports monitored — we'll email you whichever drops first.
Domestic connections to international flights elsewhere: Only book MDW-to-LAX or MDW-to-PHX positioning if you're seeing $150+ per person savings versus ORD direct international, and you're comfortable with separate ticket risk. We see viable positioning plays maybe once per quarter in our monitoring. The math usually favors ORD's international bank.
You live south/southwest of Loop and flying Mexico: Midway's location advantage might matter here if Southwest's fares are within $50 of ORD options and you value the shorter transit. But we'd still check ORD first — United and American often run sales that beat Southwest's "low fare" marketing.
FAQ: ORD vs Midway for International Flights
Does Midway have any international flights besides Mexico?
As of our current monitoring, no. Midway serves Cancun, Puerto Vallarta, and Cabo San Lucas seasonally on Southwest, with occasional charter service to Caribbean destinations. Every other international route from Chicago departs O'Hare. MDW's customs facilities can't handle the volume or diversity of international carriers that ORD processes daily.
Is O'Hare cheaper than Midway for international flights?
For the three Mexico routes both airports serve, prices are usually within $40-60 roundtrip, with ORD often winning on peak dates when Southwest's demand-based pricing spikes. For everywhere else, ORD is the only option, so there's no Midway comparison. From our monitoring, ORD's international fares price competitively with other major U.S. hubs like JFK, LAX, and SFO on most long-haul routes.
Can I connect through Midway to reach international destinations?
Technically yes if you book Southwest to a city with international service (LAX, PHX, DEN), then separately book your international flight. But you're taking on all the risk of separate tickets, adding hours of connection time, and usually paying more than an ORD direct flight would cost. We almost never see this strategy make financial sense in our fare monitoring.
Which airport is easier to navigate for international connections?
O'Hare, despite being larger. Terminal 5 centralizes most international departures and arrivals, with ATS trains connecting to domestic terminals for same-ticket connections. Midway's compact size helps for domestic Southwest flights, but its limited international service means you'd be connecting elsewhere anyway — adding complexity instead of reducing it. If you're flying internationally from Chicago, build your trip around ORD.