Midway to O'Hare Airport TransferFlat $99 airport to airport
Connecting between Chicago's two airports? Skip the shuttle shuffle. Our cross-town transfer runs Midway to O'Hare with flight tracking at both ends and luggage help, from $99.
Airport to AirportMidway to O'Hare airport transfer is a cross-town car service covering about 25 miles between Chicago's two airports, typically 35 to 50 minutes depending on traffic, at a flat rate of $99 with flight tracking at both airports.
Built for travelers with connections on separate tickets, split itineraries, or family arriving at the other airport, with a chauffeur who handles the luggage and the cross-town drive.
This Route at a Glance
Approximate distance and drive time; actual time varies with traffic, weather and events. Flat rate is fixed and shown before taxes and gratuity.
The Easy Way Between Midway and O'Hare
Two airports, one city, and often one traveler who needs to get from one to the other. We make that connection simple.
Midway and O'Hare sit on opposite sides of Chicago, about 25 miles apart. When your itinerary splits across both, a private cross-town transfer is far less stressful than juggling shuttles, trains and rideshares with your luggage in tow.
We track both flights, your arrival at one airport and your departure from the other, so your chauffeur times the pickup to your real landing and gets you across town with a comfortable buffer. Your driver meets you, handles the bags, and knows the fastest cross-town route for the time of day.
The rate is a flat $99 in either direction, ORD to MDW or MDW to ORD. Because this is a longer, cross-town trip, we especially recommend leaving enough time between flights and letting us know both flight numbers when you book.
What the Cross-Town Route Looks Like
A longer trip than the downtown runs, so timing matters.
From Midway, O'Hare transfers typically take I-55 to the Tri-State (I-294) or the Kennedy (I-90) north toward O'Hare, depending on traffic. Your chauffeur chooses the fastest path for the time of day and drops you at your specific O'Hare terminal.
O'Hare has several terminals, with domestic airlines spread across Terminals 1, 2 and 3 and most international departures at Terminal 5. Tell us your airline or terminal when you book so we drop you at the right door, close to your check-in.
- Pickup: curbside or meet and greet at your arrival airport
- Route: typically I-55 to I-294 or I-90 across town
- Drop-off: your exact O'Hare terminal, or your Midway door
- Timing: allow a comfortable connection window between flights
Riverwalk to runway
Chicago is a beautiful city to move through. We make getting to Midway just as smooth.
Who Takes This Route
Cross-town airport transfers solve a very specific set of problems.
Split Itineraries
Booked on separate tickets that land at one airport and depart from the other? We bridge the gap.
Meeting Arrivals
Land at Midway and need to collect family or colleagues arriving at O'Hare, then continue together.
Crew and Staff
Reliable, on-time cross-town transfers for flight crews, staff and teams moving between the airports.
Good to Know About O'Hare
A few O'Hare details that help us drop you in exactly the right place.
Terminals 1, 2 and 3
Most domestic airlines operate from these connected terminals. Tell us your airline for the right drop-off.
Terminal 5
O'Hare's main international terminal, used by most overseas and some domestic carriers.
Terminal Transit
O'Hare is large, so dropping at the correct terminal saves you a long internal walk or train ride.
Luggage Help
Your chauffeur handles bags at both ends, which matters most on a cross-town connection.
Connection Buffer
Cross-town traffic varies. A comfortable time gap between flights keeps the transfer stress-free.
Airport Hotels
If your layover is long, we also serve the hotels around both airports.
A 2025 to 2026 Fleet for Every Airport Ride
From solo executive pickups to full group charters, we match the right vehicle to your party size and luggage. Hourly charter rates shown; airport transfer rates on each vehicle page.
from $135/hrCadillac Escalade
Our flagship SUV. A first class arrival with commanding presence and plenty of cargo room.
View Escalade
from $100/hrLincoln Navigator
Premium SUV comfort with a quiet, refined cabin. The sweet spot for executives and travelers.
View Navigator
from $160/hrMercedes Sprinter Van
Move the whole team, family or wedding party in one vehicle, with room for everyone's bags.
View Sprinter
from $95/hrFord Expedition
Roomy full size SUV with space for extra luggage. A comfortable, budget friendly choice.
View Expedition
from $145/hrStretch Limousine
The classic stretch for weddings, proms, nights out and milestone celebrations across Chicagoland.
View Stretch Limo
from $325/hrCoach Bus
For corporate groups, conventions and events, our coach bus moves everyone together in comfort.
Request a QuoteWhat Affects Your Drive Time
This is the longest of our local routes, so plan a little extra.
Traffic and Time of Day
Cross-town expressways vary widely by hour. Rush periods can push the trip toward the upper end.
Weather
Snow and heavy rain slow the cross-town drive. Your chauffeur adjusts the route and timing.
Terminal Choice
Your O'Hare terminal changes the final approach. Share your airline so we drop at the right one.
Connection Window
The tighter your gap between flights, the more buffer you should leave for the cross-town leg.
Tips for This Route
How to make an airport-to-airport transfer smooth.
- Give us both flight numbers so we can track your arrival and time the O'Hare drop-off to your departure.
- Leave a comfortable window between flights, since the cross-town drive is longer and traffic varies.
- Tell us your O'Hare airline or terminal so your chauffeur drops you close to check-in.
- Choose meet and greet at your arrival airport so your driver is waiting when you land.
- The flat $99 rate applies from O'Hare to Midway as well, not just Midway to O'Hare.
- Traveling with a group or extra luggage? A Sprinter van makes the cross-town trip in one vehicle.
Ready when you are
Reserve online in a couple of minutes. Add your pickup, drop-off and any flight details, choose your vehicle, and your chauffeur handles the rest, timed to your schedule.
Midway Limo Service Rates and Pricing
Hourly charter rates and airport transfer flat rates, side by side. Taxes and gratuity are shown at booking, with no surprise meters.
What is included. Starting rates are shown before taxes and gratuity. Applicable taxes and gratuity are added at booking, and any additional tip for your chauffeur is optional.
Other Popular Midway Trips
Other popular Midway routes and destinations our passengers book.
Chicago and Midway, Covered
From the Riverwalk and Navy Pier to the Midway terminal, we run every ride in between.
Why Choose Midway Limo Service
Flight-tracked pickups
Real time monitoring on every arrival, with wait time built in for delays and early landings.
Up-front pricing
Clear starting rates with taxes and gratuity shown at booking. No surprise meters or hidden fees.
Professional chauffeurs
Courteous, background checked drivers who know Chicago traffic and get you there smoothly.
Midwest-wide reach
Milwaukee, Indianapolis, Notre Dame, Lake Geneva and beyond, door to door in one ride.
Meet and greet ready
Choose curbside or an in terminal greeting at baggage claim with luggage assistance.
Available 24/7
A red eye landing or a 5 a.m. departure, we run around the clock so your schedule always works.
Frequently Asked Questions
How much is a Midway to O'Hare transfer?
How long does the cross-town trip take?
Do you track both of my flights?
Which O'Hare terminal will you drop me at?
How much time should I leave between flights?
Is this cheaper than a shuttle or rideshare?
Can you carry a group across town?
Do you also go from O'Hare to Midway?
Will my chauffeur help with luggage?
Is the service available overnight?
What if my incoming flight is delayed?
How do I reserve a Midway to O'Hare transfer?
Reserve Midway to O'Hare
Flat $99, flight-tracked at both airports, with luggage help across town. Book your cross-town transfer now.