Chicago O’Hare to Chicago Midway · 25 mi · about 40 min
O’Hare to Midway Car Service
Two Chicago fields, one reservation, and luggage that only gets handled once.
Twenty-five miles sit between the two Chicago airports and no single train crosses them, so the connection becomes a road trip nobody planned. A uniformed chauffeur collects you in the lane O’Hare reserves for chauffeured cars and sets the cases down at your Midway concourse.
- 25 miORD to MDW
- 40 minOn clear roads
- 24/7Dispatch answers
- One quoteFor the whole vehicle
Why riders book Executive Transportation
Chauffeured since 2004Dispatch answers around the clockUniformed chauffeursBoth Chicago fields on one booking
The run at a glance
Across Chicago, O’Hare to Midway
Chicago O’Hare to Chicago Midway is 25 mi and about 40 min on clear roads, a short distance that behaves like a long one because every mile of it is city. The figure is the best case, which is why a connection built on it wants a cushion.
- The run25 miThe O’Hare terminal roadways to the Midway concourse doors
- Clear roads40 minThe calibrated drive, before the city has an opinion
- Terminals4 and 1Four passenger buildings at O’Hare, one at Midway
Through the city, and the hour decides how long it takes
This is the run where the distance tells you almost nothing. Twenty-five miles between the northwest side and the southwest side can be a clean half hour or the better part of two, depending on the hour and on whatever has happened ahead of you. A chauffeur picks the way that is moving.
Working the transfer backward from the onward departure
Start at the flight leaving Midway, not the one landing at O’Hare. One carrier publishes a two hour arrival at the terminal for a domestic departure, closes checked bags 45 minutes out and wants passengers at the gate 15 minutes before pushback. Add the crossing and a bag claim at the first airport.
What the quote covers
The vehicle and chauffeur are quoted by the hour, with the minimum number of hours stated up front, and one figure covers the whole vehicle. A coordinator builds the hours from both flights and the traffic this crossing is known for, so nothing is settled in the car.
Roadway, lane and terminal rules at both airports are the Chicago Department of Aviation’s own, from flychicago.com, checked September 17, 2026. The drive figure is the calibrated Central Illinois table this site publishes everywhere. Carrier deadlines were checked September 15, 2026, and belong to one airline, not to all of them. Both airports revise these pages, so confirm anything time sensitive before you fly.
How the run goes
The crossing, and the one back the other way
Two airports, four levels, and two lanes where a chauffeured car may stand.
Outbound
O’Hare arrivals to the Midway doors
- Send both flight numbersThe inbound into O’Hare and the outbound from Midway, with both scheduled times. The vehicle is held against those two lines.
- Bags first, Customs in Terminal 5Baggage claim at O’Hare sits on the lower level. An international arrival clears Customs and Border Protection in Terminal 5 before it reaches the carousel.
- Met inside at baggage claimYour chauffeur meets you inside at baggage claim, takes the luggage and walks you out to the vehicle. O’Hare lets liveries load only in the lower level center lane, lane 2, with livery parking across from each terminal, so you never stand outside waiting.
- Upper level at your Midway concourseMidway takes departures at the doors of any concourse on the upper level roadway. Name the letter on the boarding pass and you step out at the right ones.
Return
Midway arrivals back to an O’Hare departure
- Book it as one reservationThe reverse crossing is the same booking and the same vehicle, pinned to the two flight numbers you gave us. Call dispatch the moment either one moves.
- Met inside at baggage claimYour chauffeur meets you inside at baggage claim, takes the luggage and walks you out to the lower level center lane at Doors 1 and 2, where Midway sends liveries and pre-arranged cars.
- Nobody waits outside at a Chicago airportUnattended vehicles are ticketed and towed at Midway, so the car holds in the 90-space cell phone lot at 61st Street and Cicero Avenue until you have been met, then comes to the door.
- Upper level at your O’Hare terminalDepartures at O’Hare go to the upper level roadway. Terminals 1, 2 and 3 are domestic and Terminal 5 is international, so the boarding pass decides the door.
Ways to make this trip
Midway to O’Hare: the car, the trains, or a hailed ride
There are three ways to cross Chicago between the two airports, and the bags usually decide which. A single traveler with a backpack and a long layover can ride the city’s rail system and save real money. Two suitcases, a tight connection or a party of five is where a booked car wins.
No published figure for the rail trip or the hailed ride is printed here, because neither is a number we have verified and both move with the hour. Amtrak is a different trip again: its Chicago station is Union Station downtown, not either airport.
The free Airport Transit System links O’Hare’s own terminals around the clock, and it does not reach Midway. Longer reading on both fields: the Midway parking and terminal guide, the Terminal 5 guide and when to leave for O’Hare.
Whichever way you cross, the 25 miles are the same. One of them carries the suitcases.
Private jets and charter
Private jet and charter between the two fields
Both Chicago airports keep a general aviation side that has nothing to do with the concourses, and some of the traffic crossing the city moves between them.
- 01
One operator on the O’Hare side
O’Hare lists a single fixed base operator on its own FBO page, and none of the lower level lane rules reach it. The car waits at that door instead.
- 02
Two operators at the Midway end
Midway names two on its own general aviation page, on opposite sides of the field. Tell us which one your operator files to and that is the address the vehicle is sitting at.
- 03
Airline one way, aircraft the other
Much of this work is one airline leg and one charter leg: a terminal door at one end, an FBO door at the other, one reservation.
- 04
A Sprinter takes the manifest
Ten or twelve off a charter fit one Sprinter van with the hard cases. Past fourteen it becomes a coach, still quoted for the vehicle.
The operators at each end of this run
- Signature Flight SupportPatton Drive, Bldg. 825, Chicago, Illinois 60666The only fixed base operator O’Hare lists on its own FBO page. Signature says the facility is staffed around the clock, which is what a charter arriving at 2 a.m. needs.
- Atlantic Aviation6150 South Laramie Avenue, Chicago, Illinois 60638One of the two operators Midway lists on its own general aviation page. The Laramie Avenue side of the field, well away from the concourse roadways.
- Signature Flight Support5821 South Central Avenue, Chicago, Illinois 60638The second operator on the airport’s list, on Central Avenue. Tell us which of the two your operator files to and the car waits at that door.
Send the tail number, the operator and the scheduled times at both ends, and call dispatch if any of them moves. We prefer 72 hours’ notice, but call anytime. Short-notice trips depend on availability.
Airport-to-Airport TransfersO’Hare car serviceMidway car service
Executive Transportation drives to the aircraft. We do not charter it.
Request a QuoteCall (217) 523-5466Private jet shuttleThe fleet
Fleet for the cross-city run
Forty minutes is short, so the luggage decides the vehicle on a connection like this one, and the figure you are quoted buys the whole cabin.
Executive Sedan
One or two travelers with cabin bags and a connection waiting. The quietest way across.
View vehicle
Luxury SUV
Five or six people whose bags came off a carousel rather than an overhead bin.
View vehicle
Sprinter Van
A whole inbound crew and its cases moved once, with a stand-up aisle and a luggage bay behind.
View vehicle
Groups of 15 to 35
Teams and delegations arriving on one flight and leaving on another. Shuttle coaches seat 22 to 35, limousine coaches 25 to 30.
Shuttle CoachLimousine CoachEach one arrives with a chauffeur in uniform. A party of eight to ten takes the stretch limousine.
See the full fleetRequest a Quote
Book this run
Book O’Hare to Midway.
Send both flight numbers, both scheduled times and the headcount. What comes back is the vehicle, the hour and the door the car will be standing at.
(217) 523-5466We prefer 72 hours’ notice, but call anytime. Short-notice trips depend on availability.
Other runs
Other runs into the Chicago fields
Plenty of trips that end at one of these two airports start a long way south of the city, and each card below is a page of its own.
Direction changes nothing: one vehicle, one quote, the flight numbers on the reservation.
Every figure here is the clear-road drive out of the same calibrated table, and weekday Chicago traffic sits outside all of them. The airports page lists the rest of the fields.
One booking covers the outbound and the return, whichever fields they use.
What riders say
Riders on the Chicago runs
Our group of 7 needed a ride from Chicago O’Hare to Springfield. The vehicle was clean and comfortable.
Executive Transportation saved the day after another bus company fell through last minute.
The scheduling process was seamless, and the timely pickup from Bloomington airport made my journey stress-free.
Landing at one Chicago field and leaving from the other is ordinary corporate travel, and corporate airport transfers put the party in one vehicle.
Agency staff and visiting delegations cross the city the same way, through our government travel service.
Questions about this run
What travelers ask before booking O’Hare to Midway
The answers use the calibrated crossing above and both airports’ own guidance.
How long does it take to drive from O’Hare to Midway?
Executive Transportation schedules Chicago O’Hare to Chicago Midway at 25 mi and about 40 min on clear roads. Every mile of it is city driving, so a weekday afternoon stretches it past that. Build the connection on the flight times, not the drive.
Call (217) 523-5466 or request a quote.
How much connection time do I need between the two Chicago airports?
Executive Transportation works backward from the departing flight. One carrier asks domestic passengers to be at the terminal two hours out, closes checked bags 45 minutes before pushback, and wants everyone at the gate 15 minutes before. Add baggage claim at the first airport and the crossing itself.
How is the price set on an O’Hare to Midway transfer?
Executive Transportation quotes the vehicle and chauffeur by the hour, with the minimum number of hours stated up front in the written quote. The hours the crossing takes decide the figure, along with the vehicle and whether the return leg is held too. Everyone in the car rides on that single figure.
Request a Quote with both flight numbers.
Where does the chauffeur meet me at O’Hare and drop me at Midway?
Your chauffeur meets you inside at O’Hare’s baggage claim, takes the luggage and walks you out to the lower level center lane, lane 2, the only place the airport lets a livery load. At Midway you are dropped at the terminal door on the upper level roadway, at the concourse your boarding pass names.
See the Midway car service page.
Is the train from O’Hare to Midway cheaper than a car service?
For one traveler with light bags and time to spare, yes, and we say so plainly. The city rail system reaches both airports, but not on one line, so it means a train downtown, a change of lines and the suitcases going with you both times.
Call (217) 523-5466 if the connection is tight.
Which vehicle should a group book for the crossing?
Executive Transportation fits two or three travelers into an executive sedan, five or six into a luxury SUV, fourteen into a Sprinter van and larger parties onto a coach seating up to thirty-five. Count the checked bags coming off the inbound first.
Compare the full fleet.
Do you meet private jet and charter flights at both fields?
Yes. O’Hare names one fixed base operator on its own page, Signature Flight Support, and Midway names two, Atlantic Aviation and Signature. The car sits at the FBO door of whichever operator your flight uses rather than at the airline terminal, and the crew and the passengers ride on one booking.
Send the tail number when you book the chauffeur.
Keep reading
More on the two Chicago fields and the gap between them
The long guides, the pages at each end, and the services this crossing belongs to.
From the blog
Both fields at length.
- Midway Parking Cost and Terminal GuideOne terminal, three concourses, every posted rate.
- O’Hare Terminal 5: A Traveler’s GuideCustoms, the transit train and the arrivals hall.
- O’Hare Security Wait Times: When to LeaveWorking a departure back to an hour.
- O’Hare Parking Cost vs. a Car ServiceWhat the official lots charge.
Both ends of the run
The pages at either end.
Services and corporate
How a crossing like this is arranged.
Book the ride
Request your O’Hare to Midway ride
Three things travelers on this connection say mattered.
The bags are handled once
Everything goes in the car at the first airport and comes out at the second, with nothing riding a train on your lap.
Held against both flight numbers
The booking carries the inbound and the outbound, so a coordinator already knows what the crossing is serving.
Somebody answers whatever the hour
A late landing at one field and a dawn departure from the other are both normal here.
Photo credits
- Aircraft lined up along the terminal at Chicago Midway International Airport, via Wikimedia Commons. Photo by Ken Lund, CC BY-SA 2.0, source.
- Downtown Chicago seen from the Kennedy Expressway, via Wikimedia Commons. Photo by Ken Lund, CC BY-SA 2.0, source.