O’Hare to Midway Connection: How Long to Allow and When a Private Car Helps

Written by the Milwaukee to O’Hare dispatch team | Published October 21, 2026 | 14-minute read

An O’Hare to Midway connection is different from changing terminals at one airport. Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are separate facilities, located in different parts of the city. Travelers connecting between them must leave the first airport, arrange ground transportation across Chicago, and complete the necessary check-in and security procedures at the second airport. When coordinating Chicago airport car service, understanding that process is essential to choosing a workable itinerary.

Connecting Between O’Hare and Midway?

Call (414) 387-6619 or Get a Private Airport Transfer Quote.

Share both flight numbers, arrival and departure dates, passenger count, luggage requirements, and your available connection window. Our reservations team can discuss a prearranged airport-to-airport transfer, subject to service availability and applicable Chicago licensing requirements.

The most important question is not simply how long the drive takes. Passengers must also account for deplaning, baggage collection, immigration where applicable, finding the pickup location, travel between airports, checking baggage again, security screening, and reaching the next gate.

A private car may reduce some of the physical transfers and luggage handling involved in the journey. It cannot eliminate traffic, airline requirements, or the risk of a delayed incoming flight.

Quick Answer: An O’Hare to Midway connection requires ground transportation between two separate airports. The Chicago Department of Aviation advises allowing up to two hours for the CTA train journey, which involves the Blue Line, a transfer at Clark/Lake, and the Orange Line. Private car travel is direct but depends on road conditions. The full connection window must also include time to exit the arriving aircraft, collect luggage, check in at the next airport, clear security, and reach the gate. A short gap between flights may be insufficient even with a reserved chauffeur.

O’Hare to Midway Connection: Quick Facts

These details are based on published airport and transit guidance. Actual travel conditions and airline procedures should be checked for the travel date.

O’Hare to Midway: How Long Does the Connection Take?

There is no single guaranteed connection time because the journey has several separate stages.

Some travelers arrive on a domestic flight with carry-on luggage only. Others arrive internationally, must clear customs, and then retrieve several checked bags.

A passenger who is already outside the arrival terminal can begin ground transportation much sooner than someone who has just landed.

The stages of an airport-to-airport connection

A complete journey involves:

1. Arriving at O’Hare and leaving the aircraft.
2. Collecting checked luggage, if applicable.
3. Completing U.S. immigration and customs procedures when required.
4. Reaching the ground transportation pickup point.
5. Traveling from O’Hare to Midway.
6. Checking in and dropping bags at Midway when necessary.
7. Completing TSA security screening.
8. Walking to the departure gate before boarding closes.

The same planning principles apply in reverse when traveling from Midway to O’Hare.

A useful transfer plan accounts for every stage instead of treating the road journey as the entire connection.

How much time should you allow?

Start with the second airline’s required check-in and boarding deadlines.

Then work backward through the airport-to-airport transfer and the likely arrival procedures at the first airport.

For example, suppose a traveler allows 45 minutes to deplane and collect luggage, two hours for CTA transportation based on the airport’s published guidance, and two hours before the next flight for check-in, security, and boarding preparation.

Those assumed stages total 4 hours and 45 minutes, before adding an additional disruption buffer.

This is an illustrative planning calculation, not an official minimum connection time or a prediction of how long each stage will take.

Passengers with international arrivals, multiple checked bags, separate airline tickets, mobility needs, or particularly inflexible departures may need significantly more time.

Connecting Between O’Hare and Midway by CTA Train

Public transportation can be an economical choice for travelers who have sufficient time and can comfortably manage their luggage.

The Chicago Transit Authority connects O’Hare and Midway through downtown Chicago.

However, there is no single CTA train running directly between the two airports.

Step 1: Take the Blue Line from O’Hare

At O’Hare, follow airport signs toward the CTA Blue Line station.

The station is accessible from the main terminal complex near Terminal 2.

Passengers arriving at Terminal 5 may need to use the airport’s internal transportation system to reach the CTA station.

Board a Blue Line train heading toward downtown Chicago.

Step 2: Change trains at Clark/Lake

Leave the Blue Line at Clark/Lake in downtown Chicago.

Follow signs to the Orange Line platform.

The transfer involves moving between train levels, which can take additional time when carrying luggage or traveling with children.

Check current CTA station access and elevator information before traveling if step-free access is necessary.

Step 3: Take the Orange Line to Midway

Board an Orange Line train heading toward Midway.

At the final station, follow the enclosed pedestrian connection toward the terminal.

Proceed to the appropriate airline check-in area or security checkpoint.

The airport advises allowing up to two hours for the CTA journey between O’Hare and Midway.

That guidance does not include all the additional time a passenger may need before leaving the first airport or after arriving at the second.

Important overnight consideration

The CTA Blue Line operates around the clock, but the Orange Line does not offer normal overnight train service.

Travelers with late-night or very early connections should review the current Orange Line schedule.

Do not assume that because the Blue Line operates overnight, the complete two-train airport connection will be available at every hour.

When CTA makes sense

The train may be appropriate when the passenger has a generous connection window, limited luggage, and no difficulty navigating stations.

It may be less practical for a family with several suitcases, an international arrival with uncertain baggage timing, or passengers facing a very early or late transfer.

Before choosing public transportation, review the specific departure times and service alerts.

Private Car Service Between O’Hare and Midway

A private transfer offers a different experience from the CTA journey.

Instead of reaching the train station, changing lines downtown, and walking from the second station to the terminal, the passenger travels by road between the agreed airport pickup and drop-off locations.

A prearranged professional chauffeur service may be useful for business travelers, families, and passengers carrying substantial luggage.

Direct transportation between airports

A confirmed private car reservation establishes the pickup airport and departure airport in advance.

The chauffeur follows the appropriate roadway route based on current conditions and authorized airport access.

Unlike the CTA journey, the passenger does not need to change trains.

The transfer remains subject to Chicago traffic, possible construction, and delays near the terminals.

Private transportation is not a guaranteed faster connection

A private car can eliminate the downtown train transfer and reduce luggage handling.

That does not mean it will always reach Midway sooner than public transportation.

Congestion on major roads, incidents, and severe weather can make road travel unpredictable.

For an airport connection with little time available, a private vehicle cannot guarantee that the next flight will be reached.

Booking the correct service

A passenger considering airport car service should request a quotation for the precise ORD-to-MDW or MDW-to-ORD journey.

An advertised rate for transportation from Milwaukee to O’Hare does not automatically apply to a transfer entirely within Chicago.

Chicago-originating rides must be coordinated with appropriately licensed chauffeurs through the applicable affiliate arrangements.

Confirm the specific service, vehicle, and quotation before making travel decisions.

Comparing Train, Taxi, Shuttle and Private Car Options

Every transfer method has advantages and limitations.

Taxi transportation

Taxis are available at designated locations at both airports.

The actual cost and driving time depend on traffic and the applicable fare structure.

Passengers should use authorized taxi locations rather than accepting unsolicited transportation offers.

Shuttle transportation

Shuttle services at Chicago airports may include hotel transportation, regional buses, charters, and other scheduled services.

Do not assume that an airport shuttle travels directly between O’Hare and Midway.

Confirm the exact route, operating schedule, baggage allowances, pickup instructions, and required reservations before treating a shuttle as a connection option.

Choosing the right option

A solo traveler with one carry-on and a generous layover may prefer CTA.

A family with multiple bags may value a vehicle reserved specifically for its party.

An executive assistant arranging a connection for a visiting client may prefer advance coordination and a confirmed pickup procedure.

The best choice depends on the connection window, travel requirements, and the passenger’s priorities—not solely on the type of vehicle.

Where to Meet Your Chauffeur at O’Hare

O’Hare has several passenger terminals, and the appropriate pickup arrangements depend on the arriving flight and the transportation category.

For a prearranged chauffeur reservation, passengers should receive terminal-specific instructions rather than assuming that every arrival uses the same door.

Confirm the arrival terminal

The pickup plan begins with the airline and flight number.

A passenger arriving through Terminal 5 may have different ground transportation requirements from a traveler arriving through Terminals 1, 2, or 3.

The company’s O’Hare airport transportation page provides an overview of its airport service arrangements.

Use authorized commercial pickup areas

The Chicago Department of Aviation identifies designated areas for prearranged limousine and livery vehicles.

The specific meeting instructions should be supplied by the transportation provider and may vary with airport operations.

A passenger should not wait indefinitely at an arbitrary terminal curb.

Meet-and-greet arrangements

For an unfamiliar airport or a guest arriving internationally, airport meet-and-greet service may be worth requesting.

When available and permitted, a chauffeur may greet the passenger at an agreed public arrivals location.

The service must be confirmed as part of the reservation, including the appropriate meeting location and any applicable additional arrangements.

Arriving at Chicago Midway for Your Second Flight

Midway has a more compact terminal layout than O’Hare, but the passenger must still meet the airline’s departure requirements.

A private vehicle can bring the traveler to an appropriate departures drop-off area.

From there, the passenger remains responsible for check-in, baggage procedures, security screening, and reaching the gate.

Confirm the departure airline

Before leaving O’Hare, check the second flight’s status and the airline’s instructions.

A flight delay may create additional time, but an earlier boarding cutoff can still affect the connection.

Do not assume that arriving at the terminal shortly before the scheduled departure is sufficient.

Account for baggage check-in

Checked baggage may need to be presented before an airline’s baggage acceptance cutoff.

Those deadlines can be earlier than the passenger’s final boarding time.

Review the second airline’s current requirements, particularly when traveling on separate tickets.

For passengers interested in a prearranged arrival at Midway, see the company’s Midway airport service information.

Midway to O’Hare: Planning the Reverse Connection

Some passengers begin at Midway and depart from O’Hare.

The basic requirements remain the same, but the transit route runs in reverse.

CTA from Midway to O’Hare

Take the Orange Line from Midway toward downtown Chicago.

Transfer at Clark/Lake to the Blue Line heading toward O’Hare.

Continue to the O’Hare CTA station and follow airport instructions toward the appropriate departure terminal.

The Chicago Department of Aviation also recommends allowing up to two hours for this rail journey.

Private transfer toward O’Hare

A prearranged car follows an appropriate road route between the airports.

An O’Hare departure from Terminal 5 or another specific terminal should be included in the reservation details.

Airport traffic, airline check-in requirements, and the terminal’s layout all affect the total transfer plan.

Do not confuse an airport transfer with a downtown trip

Travelers sometimes compare prices for O’Hare to downtown Chicago transportation or Midway to downtown Chicago car service.

Those routes have different destinations.

Traveling between O’Hare and Midway is a separate airport-to-airport journey, so the appropriate price and service arrangement must be quoted specifically.

International Arrivals and O’Hare Terminal 5

An international arrival can add considerable uncertainty to an airport connection.

Passengers arriving from most international destinations must complete the applicable immigration and customs procedures before leaving the secure arrivals process.

Travelers arriving from certain U.S. preclearance airports may follow different procedures.

Allow time for immigration and baggage

Passport control, collecting luggage, and customs procedures can vary considerably.

The time required depends on passenger volume, flight arrival patterns, individual circumstances, and the operating conditions on the day.

A prearranged chauffeur cannot bypass immigration or customs.

Passengers should not schedule the pickup as though they will be outside the terminal immediately after landing.

Confirm whether checked luggage must be collected

When traveling between two different airports, a passenger should verify how baggage is handled by the airlines involved.

Do not assume that bags will automatically reach the next flight at the second airport.

Ask the airlines whether the traveler must collect baggage, transport it between airports, and check it again.

Be cautious with separate tickets

If the two flights were purchased separately, the first airline may not be responsible for a missed onward flight on the second booking.

The rules vary according to the airlines, ticket conditions, and itinerary.

Passengers should review those conditions before booking a connection that involves crossing Chicago.

How Traffic Changes the Airport Connection

Driving between O’Hare and Midway requires traveling through the Chicago metropolitan road network.

The route may vary depending on the time, traffic, construction, and terminal access.

Rush-hour conditions

Weekday morning and afternoon congestion can affect travel.

A journey that seems straightforward on a map may take considerably longer when roads are busy.

Travelers should review a current route estimate for the actual date and time rather than relying on a single generic driving-time claim.

Construction and incidents

Road construction can change lane availability, access ramps, and travel patterns.

Unexpected incidents may affect the route after the chauffeur has already departed.

An experienced driver may adjust the route when appropriate, but alternate roads are not guaranteed to eliminate delays.

Winter and severe weather

Snow, freezing rain, poor visibility, and other severe weather conditions can affect airport access and road travel.

A connection that appears reasonable under normal conditions may become difficult during a major storm.

Travelers with especially tight itineraries should consider whether an airport change is appropriate when severe weather is expected.

When a Private Car Helps With Luggage and Groups

Convenience becomes more important when several passengers need to move together between airports.

Families with checked baggage

A family with multiple suitcases may find the Blue Line and Orange Line transfer more demanding than a direct vehicle journey.

A private SUV allows the group to remain together between the agreed pickup and drop-off points.

However, the reserved vehicle must have enough usable space for every passenger and bag.

Executive travelers

Business travelers may prefer a direct transfer to avoid carrying luggage through downtown stations.

Employers arranging corporate transportation can coordinate the booking through an authorized assistant or travel manager.

The organizer should have access to both flight numbers and the passenger’s contact information.

Larger parties

A group transferring between airports may need more capacity than one SUV provides.

The company’s group transportation service offers options that can be discussed for suitable group itineraries.

Confirm seating, luggage accommodation, vehicle availability, and the applicable service minimums.

Choosing a vehicle

Available categories include executive sedans, luxury SUVs, and larger vehicles.

Review the vehicle fleet before reserving.

The correct choice should reflect the actual passenger count and luggage requirements rather than simply selecting the largest advertised vehicle.

What Happens if the First Flight Is Delayed?

A delayed arrival can consume time originally reserved for the airport transfer.

This is especially important when the passenger has separate airline tickets or a second flight with limited rebooking options.

Recalculate the connection immediately

If the first flight is delayed, compare the new expected arrival time with the second airline’s check-in and boarding requirements.

A private car reservation does not create additional time at the second airport.

Contact the transportation provider

Share the updated flight information and confirm whether the pickup arrangement can be adjusted.

If the arriving flight number or airport changes, communicate that change promptly.

Review the company’s cancellation policy and contact dispatch about flight disruptions.

Contact the airline

If the connection becomes unrealistic, contact the relevant airline as early as possible.

Ask about rebooking options and the consequences of missing the departure.

A transportation provider can help arrange ground travel, but it cannot guarantee airline rebooking or boarding.

Booking a Private O’Hare–Midway Transfer

When requesting an airport-to-airport ride, provide the complete itinerary rather than only asking for transportation from O’Hare to Midway.

Information needed for the booking

Have these details ready:

1. Arrival airport and flight number.
2. Arrival date and scheduled landing time.
3. Departure airport and flight number.
4. Scheduled departure time.
5. Arrival terminal, if known.
6. Number of passengers.
7. Checked and carry-on luggage.
8. Any mobility or child seating requirements.
9. Whether tickets are separate or part of one airline itinerary.
10. Passenger contact information.
11. Preferred vehicle.
12. Any special pickup instructions.

Confirm the written quotation

The reservation should identify the agreed transfer, vehicle class, pickup arrangements, and applicable charges.

Do not apply a published Wisconsin-to-Chicago airport rate to a Chicago-internal journey without a specific quotation.

Ask about the treatment of tolls, waiting, flight delays, cancellation conditions, and changes in the scheduled pickup time.

Confirm Chicago licensing arrangements

Chicago-originating transportation must comply with the applicable City of Chicago requirements.

Milwaukee to O’Hare operates as a division of Pharaoh’s Transportation and coordinates appropriate affiliate arrangements for rides beginning in Chicago.

The specific service and authorized operating arrangement should be confirmed before booking.

For additional information about transportation planning, see the company’s Chicago service area guide and information about its professional chauffeurs.

When Should You Avoid an Airport Change?

Not every two-airport connection is a reasonable itinerary.

Passengers should examine whether the journey introduces unnecessary risk.

The connection is exceptionally short

When the time between scheduled flights does not comfortably cover baggage collection, ground transportation, security, and boarding, the itinerary may be unsuitable.

A reserved vehicle does not make a very short connection safe.

The incoming flight is international

International arrival procedures can vary significantly.

A tight connection involving customs and a separate airport creates more uncertainty than an ordinary domestic connection at one airport.

Several travelers have substantial luggage

Groups need more time to collect bags, meet the vehicle, board together, and complete the second airport’s procedures.

A schedule that may work for a solo traveler with carry-on luggage may not work for a family or group.

Overnight public transit is limited

The Orange Line does not run throughout the entire night.

If the itinerary depends on an overnight transfer, check the actual CTA schedule and compare available alternatives.

The second flight is difficult to replace

A passenger catching the last flight of the day or an important international departure should consider the consequences of missing it.

Where possible, selecting flights through the same airport may reduce unnecessary complexity.

Frequently Asked Questions About O’Hare to Midway Connections

1. How long should I allow for an O’Hare to Midway connection?

Allow enough time for the arriving flight, baggage, transportation, second-airport check-in, security and boarding. Chicago’s airport authority advises allowing up to two hours for the CTA journey alone. The full connection window must be longer.

2. How do I travel from O’Hare to Midway on public transportation?

Take the CTA Blue Line from O’Hare to Clark/Lake, transfer to the Orange Line, and continue to Midway. Check current schedules, transfer access, and operating hours.

3. How does a private car transfer between O’Hare and Midway work?

A reserved chauffeur meets the passenger at an agreed authorized airport location and provides direct road transportation to the second airport. Traffic, terminal procedures, and the confirmed reservation determine the arrangements.

4. What is the difference between changing terminals and changing airports?

Changing terminals occurs within one airport complex. Moving between O’Hare and Midway requires leaving one airport, traveling across Chicago, and completing departure procedures at the other.

5. What happens to checked baggage when transferring between the two airports?

Baggage arrangements depend on the airline itinerary. Travelers should confirm whether they must collect their checked luggage, transport it between airports, and check it again.

6. How should I plan an international arrival at O’Hare before departing from Midway?

Allow for immigration, baggage collection, customs, ground transportation, and the second flight’s check-in and security requirements. Confirm the airline’s policies before selecting the connection.

7. What happens if the Orange Line is not operating during my connection?

Review current CTA schedules and available overnight alternatives. Depending on the itinerary, an authorized taxi or prearranged private vehicle may be more practical.

8. How does traffic affect a private airport-to-airport ride?

Traffic, construction, incidents, and weather can affect the road journey. A private car avoids the downtown train transfer but cannot guarantee a particular arrival time.

9. What vehicle should a family reserve for an airport connection?

The vehicle should accommodate the entire family and all luggage safely. An SUV may suit a smaller group, while a larger vehicle may be necessary for additional passengers or baggage.

10. How should I arrange a transfer for an executive or visiting client?

Provide both flight details, passenger contact information, vehicle requirements, and the full connection window. A designated travel coordinator should communicate any significant itinerary changes.

11. What should I do if my incoming flight is delayed?

Contact the ground transportation provider and the relevant airline. Reevaluate whether the connection remains workable and review any rebooking or reservation-change conditions.

12. How can I compare train, taxi, shuttle and private car options?

Compare the complete journey, including access to pickup locations, luggage handling, transfers, service hours, road conditions, costs, and the time available before the next flight.

Make the Entire Connection Work, Not Just the Drive

An O’Hare to Midway transfer should be evaluated as a complete airport-to-airport journey.

The CTA provides an established public transportation option through downtown Chicago, while prearranged private vehicles may reduce the need to change trains and manage luggage through stations.

Neither option removes the need for realistic scheduling.

Passengers should prioritize the second airline’s deadlines, allow for arrival delays, and avoid treating published travel times as guarantees.

For additional planning guidance, browse the company’s Chicago transportation routes or its airport travel guides.

Request a Private Transfer Between Chicago Airports

Milwaukee to O’Hare coordinates airport and chauffeur transportation through the Pharaoh’s Transportation operation, including suitable Chicago-originating reservations arranged through appropriately licensed affiliate chauffeurs.

The reservations team can discuss your flight connection, available vehicle categories, pickup arrangements, and the quotation for the requested transfer.

Call (414) 387-6619 to discuss an O’Hare-to-Midway or Midway-to-O’Hare reservation.

About the Milwaukee to O’Hare Dispatch Team

Milwaukee to O’Hare is operated by Pharaoh’s Transportation. Both brands share the Milwaukee office and dispatch team. Airport and intercity transportation reservations are coordinated according to the itinerary, vehicle availability, and applicable operating requirements.

Milwaukee to O’Hare

Address: 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207

Phone: (414) 387-6619

Email: info@milwaukeetoohare.com

Online Reservations: Book Online / Get a Quote

Reservations: 24/7

Official Resources and References

The following official resources support the airport transfer instructions and planning guidance. Travelers should check current schedules and airport operating information before departure.

• Chicago O’Hare International Airport — Transportation to Midway — Official inter-airport transfer guidance, including the CTA route and recommended rail travel allowance.
• Chicago Midway International Airport — Transportation to O’Hare — Reverse airport connection instructions and ground transportation options.
• Chicago Transit Authority — Airport Train Transportation — Official guidance for the Blue and Orange Lines serving Chicago’s airports.
• Chicago Transit Authority — Orange Line Schedules — Current Orange Line hours and service information, including overnight limitations.
• Chicago Department of Aviation — O’Hare Taxi, Limousine and Rideshare — Designated ground transportation pickup information.
• Chicago Department of Aviation — Midway Taxi, Limousine and Rideshare — Midway transportation pickup locations and commercial vehicle guidance.
• Chicago O’Hare International Airport — Connecting Traveler — Official information about domestic and international connections, baggage handling, and security requirements.