O'Hare and Midway sit on opposite sides of Chicago — northwest and southwest — which makes this one of the least intuitive transfers in air travel. There's no direct train, and the drive isn't as short as the map suggests.
The Basics
- Distance: roughly 25–27 miles by road
- Drive time: 45–60 minutes in normal traffic, 60–90 minutes during rush hour or winter weather
- Public transit: no direct connection — CTA requires the Blue Line to downtown, then a transfer to the Orange Line, totaling 1 to 1.5 hours
Why This Transfer Catches People Off Guard
Both airports serve "Chicago," so travelers sometimes assume they're close together. They're not — this is a full cross-city trip, comparable to driving across most of a major metro area. If you're connecting between the two for a same-day or overnight trip, budget real time for it, not a quick hop.
Best Options by Situation
Tight connection (under 2.5 hours): A pre-arranged car is the safer bet. It skips the taxi queue at either end and tracks your inbound flight, so if your first flight runs late, the pickup adjusts rather than leaving you stuck.
Flexible timing, budget-conscious: The Blue Line to Orange Line works, but only if you have real buffer — 1.5 hours minimum, more with luggage or during rush hour, since it involves a transfer and walking between platforms.
Rideshare: Available at both airports, but pricing and driver availability are demand-based, and a 25+ mile cross-city trip is exactly the kind of ride where surge pricing is most likely to apply.
Planning Around Rush Hour
If your connection window includes the 7–9 a.m. or 3–7 p.m. windows, add the higher end of the drive-time estimate. Chicago's cross-town routes (I-294, I-55, surface streets) all see meaningful slowdowns during these hours — a 45-minute drive at 10 a.m. can become 90 minutes at 5 p.m.
What to Share When Booking This Route
- Both flight numbers (arriving and departing) so dispatch can plan around your actual connection window, not just the scheduled one
- Terminal for both the arrival and departure airport
- Luggage count, since a tight connection with checked bags needs extra buffer
O'Hare to Midway FAQs
Is there a direct train between O'Hare and Midway?
No. CTA requires taking the Blue Line to downtown and transferring to the Orange Line — a trip of 1 to 1.5 hours total.
How much time should I budget for this transfer?
At least 2.5–3 hours between flights if driving, more if relying on public transit or during rush hour.
Is a pre-arranged car worth it for this route?
For a tight connection, yes — it removes the taxi-queue wait at either airport and adjusts automatically if your first flight is delayed.
Request Your Airport Ride
Send your trip details below. Dispatch will review your request and call or text you to confirm the ride, vehicle and final fare.
Plan the ORD-to-MDW Transfer
Share both flights and the complete luggage plan.
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