Getting Between O'Hare and Midway
Chicago's two airports are on opposite corners of the metro area. O'Hare International (ORD) is northwest, Midway (MDW) is southwest, and the drive between them is roughly 25 miles — normally 45 to 60 minutes, or 75 to 90 in weekday rush hour. There is no shortcut; the route crosses the city no matter which way you take it.
We run this transfer in both directions, 24 hours a day, as a private direct ride. Nobody else in the vehicle, no intermediate stops, and the driver meets you at your arrival terminal rather than at a shared shuttle stand.
Pricing: we quote this route individually rather than publishing a single fare, because the honest cost depends on the hour, the passenger count and how much checked luggage is moving. Call (224) 333-2462 or send the form on this page and dispatch will confirm a flat number before you commit — and it is the same number in the other direction.
Why Not the Train?
This is the question we get most, so here is the straight answer: there is no direct train between O'Hare and Midway. The CTA route is the Blue Line from O'Hare into the Loop, a walking transfer between stations downtown, then the Orange Line back out to Midway.
On paper it is cheap. In practice, with checked bags, it is 90 minutes to two hours, it involves stairs and a street-level transfer in the middle of downtown, and both lines run crowded at exactly the hours when connecting passengers travel. If you are alone with a backpack and three hours to spare, it works. If you are moving a family, checked luggage, or a tight connection, a direct car is the difference between making the second flight and not.
Rideshare covers the route too, but this is the trip where surge pricing does the most damage — a cross-city ride during a delay wave or a snow event is exactly when the multiplier peaks. A flat quote agreed in advance does not move.
How Much Time to Leave Between Flights
Allow at least four hours between your scheduled O'Hare landing and your Midway departure. Five if you are checking bags, travelling in winter, or connecting from an international arrival. That is not padding — here is where it goes:
- Deplaning and baggage claim — 20 to 45 minutes, longer at Terminal 5 where you clear customs and immigration first
- The drive — 45 to 60 minutes normally, 75 to 90 in rush hour or weather
- Check-in and security at Midway — airlines generally cut off checked bags 45 minutes before departure, and Midway security queues are unpredictable
One thing travellers routinely get wrong: if your two flights are on separate tickets, no airline moves your bags between the airports. You collect them at O'Hare, they ride with you, and you check them in again at Midway. Plan the buffer around that, not around the flight times alone.
Going the other way — Midway to O'Hare — the same math applies, and O'Hare's own check-in and security cutoffs are, if anything, less forgiving.
Where Your Driver Meets You
Starting at O'Hare:
- Terminals 1, 2, 3: Lower level, center lane (Car Services / TNP)
- Terminal 5 (International): Vestibule 5D or 5E, lower level after customs
Starting at Midway: lower level baggage claim, at the pre-arranged pickup curb. Full detail on the Midway airport taxi page and in our Midway baggage claim pickup guide.
Give us your flight number either way. We track the inbound in real time, so if you land late the car is still there and the delay costs you nothing.
Who Actually Books This Ride
- Split-ticket itineraries — a cheap fare into O'Hare and out of Midway, booked separately, is the single most common reason
- Misconnects and rebookings — when the airline rebooks you onto a flight from the other airport, often at short notice
- Carriers that only serve one airport — Midway is the Southwest hub; plenty of connections simply do not exist at O'Hare
- Cancelled flights — during a weather event the fastest recovery is frequently a seat out of the other airport
- Crew and staff repositioning — a routine, scheduled version of the same trip
Most of these are last-minute by nature. We take same-day and short-notice bookings on this route subject to driver availability — calling (224) 333-2462 is faster than the form if you are already standing in baggage claim.
Other Chicago Airport Routes
If you need one airport rather than a transfer between them:
- Taxi to O'Hare — from any Chicago suburb, flat rates published
- Taxi to Midway — same, for MDW departures
- Airport pickup — arrivals from either airport, with flight tracking
- O'Hare to downtown Chicago — flat $72
- Fare calculator — estimate any route on our network
- O'Hare vs Midway — which airport actually suits your trip