Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are separate airports on opposite sides of the city. They share no terminals and no airside connection. A traveler who lands at one and departs from the other leaves the airport system entirely, crosses Chicago on public roads or public transit, and then enters the second airport as a new departing passenger — check-in, bag drop, security screening and all.
That is the part most itinerary planning misses. This guide explains how to evaluate an ORD-to-MDW transfer realistically, how the official public transit route works, how a private prearranged car compares with taxi, rideshare and shared-ride options, and what a transportation provider needs in order to plan around your actual flights.
Why an Airport Change Is Not a Normal Connection
On a normal connection you stay inside the secure area, move between concourses on foot or by terminal train, and your checked bags travel without you.
An O’Hare-to-Midway change works differently. You clear the arrivals process, collect anything you checked, walk out to ground transportation, cross the metropolitan area, and start over at the departure airport. None of the second half is handled inside an airport system.
The Chicago Department of Aviation advises travelers connecting between the two airports to allow adequate time. That is the governing principle for everything below, and it is worth taking literally.
The Number That Actually Matters: Aircraft Door to Departure Gate
The useful figure is not the drive time between the airports. It is the total elapsed time from the moment your arriving aircraft reaches the gate to the moment you are standing at your departure gate at the second airport.
The components of the connection block
Every ORD-MDW transfer includes some or all of the following:
- Deplaning, which depends on your seat, the aircraft, and gate availability on arrival
- Immigration and customs processing, on international arrivals
- Baggage claim, if you have checked bags
- Reaching the ground transportation area and meeting your vehicle, or the train platform
- Road or transit travel between the airports
- Check-in and bag drop at the departure airport
- Security screening
- Travel from the checkpoint to the gate, plus the airline’s boarding cutoff
Which components vary the most
Deplaning, road or transit time, and security lines swing the widest. An international arrival adds immigration and customs, which varies materially by citizenship, terminal, flight and queue conditions. Checked bags add a wait at the first airport and a bag-drop step at the second. Groups, young children, strollers, sports equipment and mobility aids add time to nearly every step.
Airline check-in, bag-drop and security cutoffs are not universal either. Confirm current requirements with the operating airline and check TSA guidance for the departure airport before relying on any number.
Why this guide does not publish a minimum connection time
No single figure would be honest for every traveler. A domestic transfer with carry-on bags at midday is a different problem from an international arrival with three checked bags in evening rush. Build the block above for your own itinerary, add buffer for what you cannot control, and confirm the plan with the airlines.
Public Transit: The Blue Line to Orange Line Route
There is no single train between O’Hare and Midway. The connection requires a transfer downtown.
The official CTA routing
The Chicago Department of Aviation’s published route is the Blue Line from O’Hare to the Clark/Lake station, a free transfer to the Orange Line, and then the Orange Line to Midway. CDA advises allowing up to two hours for the airport-to-airport trip. Treat that as the airport’s planning guidance, not a promised duration.
CTA reports that the Blue Line serves O’Hare directly and normally takes about 40 to 45 minutes to reach downtown, and that the Orange Line serves Midway directly and normally takes about 20 to 25 minutes to downtown. Those are normal-condition figures. Track work, weather, crowding and service disruptions all change them, so check current schedules and service alerts for the Blue Line and the Orange Line before you travel.
At Midway, the CTA station is connected to the terminal by an enclosed walkway, which helps in winter weather and when you are moving bags.
Overnight service differs by line
This matters more than any other detail on the transit route. The Blue Line operates 24 hours a day, seven days a week; the Orange Line does not operate during overnight hours.
For a late-night O’Hare arrival or a very early Midway departure, the first half of the trip may be available while the second half is not. Verify the current first and last Orange Line trains for your travel date, and have a road-based plan ready if the timing does not work.
Traveling the route with luggage
Transit is the lowest-cost option and it is unaffected by expressway congestion. The tradeoffs are physical: you board twice, transfer at a busy downtown station, and manage stairs, escalators and platform crowds yourself. CTA trains have no dedicated luggage storage, and at peak periods you may be standing. For one traveler with a carry-on that is manageable; for a family with checked bags it is usually the hardest part of the day.
Private Prearranged Car Service
A private prearranged transfer is a scheduled reservation for your party alone, in a single vehicle, direct between the two airports. LimoRSVP can arrange a private, pre-scheduled O’Hare-to-Midway transfer subject to availability and the confirmed itinerary. It is not a shared shuttle on a fixed loop; the trip is planned around your specific flights.
What a prearranged transfer coordinates
- Both flight numbers. Provide the arriving and departing flights so the office can evaluate your actual arrival timing against the next departure.
- Vehicle selection based on luggage, not just headcount. Seats and usable cargo space are different limits. Bag count and size, child seats, mobility equipment and oversized items all affect the recommendation, so choose a vehicle for passengers and luggage with the office rather than defaulting to the smallest category that seats everyone.
- Pickup instructions issued for the reservation. Curbside procedures differ between the airports and change with construction and traffic control, so dispatch provides the meeting details for your specific trip. Our O’Hare airport car service and Midway Airport car service pages cover each airport’s arrival context.
- One point of contact. If a flight changes, call the LimoRSVP office at 312-208-7354 and dispatch updates the chauffeur. Passengers should not try to reach the chauffeur directly.
- Continuous luggage handling. Bags are loaded once and unloaded once at the departure terminal, with the chauffeur assisting.
LimoRSVP has provided chauffeured transportation since 2004. Vehicles used for service are fully insured and chauffeurs are licensed in the operating jurisdiction. Because the trip depends on two flight schedules, pricing is quoted against the reviewed itinerary rather than presented as a fixed figure.
What no road transfer can control
A private car removes the transfer, the platform crowds and the luggage carrying. It does not remove traffic. Expressway conditions, weather, construction and curb congestion affect every vehicle equally, and CDA notes the same variability in the taxi context: rates change with time of day, weather and service. No provider can promise a road travel time between the two airports, and any article that gives you one number is not describing Chicago accurately.
Taxi, Rideshare, and Shared-Ride Options
Taxis are available at both airports without a reservation, and fares vary with time of day, weather and the specific service. Nothing is arranged in advance, which is convenient on a normal day and less so when the terminal is busy.
Rideshare uses designated pickup zones separate from where prearranged livery vehicles load. You are matched to a nearby vehicle after requesting the ride, so vehicle size is not confirmed until the match is made — a real consideration for a group with checked bags. Wait times and pricing change with demand.
Shared-ride services carry multiple parties and make additional stops, which typically lowers the cost and loosens the schedule. With a comfortable window that tradeoff can work; on a tight airport change, added stops are added risk.
Comparing the Options Side by Side
| Option | How it is arranged | Luggage handling | Schedule control | Main variables |
| CTA Blue to Orange Line | Walk up; no reservation | Passenger manages bags throughout | Fixed schedules; transfer at Clark/Lake | Service alerts, crowding, no Orange Line overnight |
| Private prearranged car | Reserved against both flights | Chauffeur assists; loaded once | Scheduled for your party; direct routing | Traffic, weather, curb congestion, availability |
| Taxi | On demand at the taxi stand | Self-managed | Departs when you board | Fares vary by time, weather, service; queue length |
| Rideshare | Requested on the app at a designated zone | Self-managed; size confirmed at match | Departs after match and pickup | Demand pricing, wait times, vehicle capacity |
| Shared ride | Booked ahead or at the airport counter | Self-managed; space shared | Departure windows and added stops | Other passengers’ routing and stop count |
When an ORD-MDW Change May Be Too Tight
These factors compound quickly. Look closely if any apply:
- You have checked bags to reclaim at the first airport and re-check at the second
- You are arriving internationally and will clear immigration and customs
- The two flights are on separate tickets or unconnected airlines
- Travel falls during peak morning or evening road congestion, or in winter weather
- You are moving a large group, or traveling with young children, strollers or mobility equipment
- The transfer would occur during the Orange Line’s overnight gap
- The departure airline’s check-in or bag-drop cutoff is early relative to your arrival
If several apply at once, verify the plan with both airlines before committing to it. Rebooking to a single airport, or to a later Midway departure, is usually cheaper than missing the flight.
Separate Tickets and Checked Baggage
Do not assume your bags will follow you. Whether luggage is through-checked depends on the airlines involved, how the tickets were issued and the structure of the itinerary. When a trip involves two different airports, plan on reclaiming and re-checking your bags unless both carriers confirm otherwise in advance.
The same caution applies if the inbound flight is delayed. Airline obligations differ depending on whether the flights are on one ticket or two, so ask each carrier what protection you have before travel rather than after a delay.
What to Send for an Airport-to-Airport Transfer Quote
The more complete the details, the more useful the plan. Include:
- Arriving flight: airline, flight number, date, origin, terminal if known
- Departing flight: airline, flight number, date, scheduled departure, terminal if known
- Whether the arrival is domestic or international
- Passenger count, and bag count and size, including oversized items
- Whether the flights are on one ticket or separate tickets
- Child seats, mobility needs, or other special requirements
- The time you need to be at the departure airport, based on the airline’s cutoff
- A mobile number for the traveling party, and the booker’s contact if different
An ORD-MDW Transfer Planning Checklist
- Confirm which airport each flight uses, from the reservation rather than memory.
- Build the full connection block from aircraft door to departure gate.
- Ask both airlines whether bags are through-checked, and plan to recheck if not.
- Confirm the departure airline’s check-in, bag-drop and boarding cutoffs.
- Check current CTA schedules and service alerts if you are considering transit.
- For late-night or early-morning transfers, verify Orange Line service first.
- Match the vehicle to bag count as well as passenger count.
- Arrange ground transportation in advance when the window is tight or the group is large.
- Add buffer for what you cannot control: deplaning, customs, traffic and security.
- Have a fallback: know the next departure and what rebooking would cost.
For broader planning across both airports, our Chicago airport transportation page covers arrivals, departures and service options in one place.
Plan the Time First, Then Choose the Ride
An O’Hare-to-Midway transfer is manageable when the timeline is realistic and difficult when it is not. The transportation choice matters less than whether the connection had enough room in it to begin with. Build the full block, verify the parts that depend on your airlines, and choose the option that fits the window you actually have.
If a private transfer fits your itinerary, request an airport-to-airport transfer quote with both flight itineraries, your passenger count and your luggage count. You can also call 312-208-7354 to review the timing with the office before booking the flights.
Last reviewed: August 2026. Airport procedures, CTA schedules and airline cutoffs change; verify current information with the airport, CTA and your airlines before travel.
