You’ve just landed at MDW. Maybe the flight was bumpy, or maybe you’re just hungry, but now you’re staring at a transit map realizing you have to get across one of the most congested cities in America to catch a flight at ORD. It’s a trek. Honestly, the distance from Chicago Midway to O'Hare is only about 30 miles, but in Chicago traffic, miles are a lie. Time is the only currency that matters here.
If you have a three-hour layover, you’re probably going to miss that second flight. Don't risk it. Chicago is a city of "L" trains, sprawling tollways, and the kind of spontaneous road construction that makes GPS units weep. You need a plan that accounts for the fact that the Kennedy Expressway is basically a parking lot from 2:00 PM until, well, forever.
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The Reality of the "L" Transfer
Most people will tell you to take the train. It’s cheap. It’s consistent. It’s also a bit of a marathon. To go from Chicago Midway to O'Hare using the Chicago Transit Authority (CTA), you’re looking at a "hub and spoke" journey. You take the Orange Line from Midway into the Loop, then you transfer to the Blue Line to head out to O’Hare.
Expect this to take 90 minutes. Minimum.
If you’re lucky, the transfer at Clark/Lake is seamless. You walk across a platform or down some stairs, and a Blue Line train is right there, smelling faintly of brake dust and city life. But if there’s track work? You’re stuck. The Blue Line is currently undergoing massive renovations as part of the "Your New Blue" program, which means weekend "bus bridges" are a very real possibility. Always check the CTA website or the Ventra app before you tap your phone at the turnstile.
The Orange Line ride is actually pretty cool because you get a great view of the skyline as you approach the city from the southwest. It’s elevated. You see the Sears Tower (everyone here still calls it that, regardless of the sign) looming over the brick bungalows. Once you hit the Loop, the vibe changes. You’re in the heart of the machine.
Why the Blue Line is a Different Beast
The Blue Line is the only 24/7 line besides the Red Line, but that doesn't mean it's always fast. It runs through a lot of neighborhoods like Logan Square and Wicker Park before it finally hits the straightaway down the middle of the I-90 expressway. This is where you’ll feel the most stress. You’re sitting on a train, looking out the window at cars stuck in traffic, feeling superior—until the train slows down for a "slow zone" because the tracks are sixty years old.
It’s about $5 total if you don’t have a Ventra card. It’s the cheapest way to make the Chicago Midway to O'Hare jump, but it’s the most taxing if you have three suitcases and a stroller. There are no luggage racks on these trains. You will be that person blocking the door with a giant hardshell Samsonite. It’s okay. We’ve all been there.
Is an Uber or Lyft Actually Faster?
Maybe. Sometimes.
If it’s 10:00 AM on a Tuesday, a rideshare might get you there in 45 minutes. If it’s 4:30 PM on a Friday, you might as well bring a sleeping bag. The route usually takes you up Cicero Avenue to the I-55 (Stevenson Expressway), then onto the I-294 (Tri-State Tollway) or the I-90/94 (Dan Ryan/Kennedy).
The I-294 is often the "secret" move. It’s a tollway, so it costs a few bucks extra, but it bypasses the nightmare of the downtown junction. Drivers love it. Passengers hate the tolls, but you’re paying for the privilege of not sitting behind a semi-truck on the Kennedy for two hours.
Expect to pay anywhere from $60 to $120 depending on surge pricing. If there’s a light drizzle in Chicago, Uber prices double. It’s a local law of physics. Also, keep in mind that Midway’s rideshare pickup zone is in a specific parking garage across the street from the terminal. You have to walk. It’s not a curbside pickup like at smaller airports.
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The Shuttle Option: Coach USA
There used to be more shuttle companies, but the industry took a hit a few years back. Coach USA (often branded as Peoria Charter in some contexts or similar regional carriers) runs airport-to-airport services.
- Pros: You don't have to drive or navigate the subway.
- Cons: They run on a schedule. If you miss the bus by two minutes, you’re waiting another hour.
Check the current schedules at the ground transportation centers. These shuttles are great because they have actual luggage compartments. You can sit back, use their (admittedly spotty) Wi-Fi, and let a professional handle the I-294 merge. It’s usually around $30 to $40. It’s the middle ground between the "L" and a private car.
Driving Yourself: The Rental Car Trap
Don’t do it. Unless you are planning to stay in Chicago for a week and need a car for the suburbs, renting a car just to go from Chicago Midway to O'Hare is a logistical nightmare.
The "return" process at O’Hare is now centralized at the Multi-Modal Facility (MMF). You don't just pull up to the terminal. You drop the car, then you get on a tram (the ATS) to get to the terminals. This adds another 20 minutes to your trip. If you’re already stressed about a connection, the MMF is the last place you want to be.
Navigating the Terminals Once You Arrive
Midway is a breeze. One main building, three concourses (A, B, and C). You can walk the whole thing in ten minutes.
O’Hare is a sprawling beast. It has four terminals: 1, 2, 3, and 5. Terminal 5 is the international terminal and it’s physically separated from the others. If your flight is leaving from Terminal 5, you have to take the ATS train. If you’re coming from Midway via the Blue Line, the train station is underneath Terminals 1, 2, and 3. If you need Terminal 5, get off the Blue Line, follow the signs for the ATS, and ride it out to the international wing.
A Quick Note on Terminal 5
It’s been heavily renovated recently. More gates, better food (shoutout to Butcher and the Burger), and more security lanes. But it’s still far. If your transfer involves an international leg, add an extra 30 minutes just for the ATS transition.
The "Secret" Metra Hack
Hardly anyone does this, but if the timing is perfect, it’s the most comfortable way to travel. You can take a shuttle or a short Uber from Midway to the Wrightwood or Ashburn Metra stations on the SouthWest Service line. Take that into Union Station. From Union Station, you walk across the street to the Ogilvie Transportation Center and catch the North Central Service to O’Hare.
Wait. Actually, don't do that. It sounds like a pro move, but the North Central Service has very limited weekday-only runs. I mention it only because some "travel hackers" suggest it, but for a standard traveler, it’s a recipe for getting stranded in a commuter station with no snacks. Stick to the Blue Line.
What to Eat While You Wait
If you’ve made the trek and arrived early, don't eat at the first place you see.
At Midway, Reilly’s Daughter is a classic Irish pub vibe if you need a drink to calm the nerves. For food, Manny’s Deli has a satellite location there. Get the corned beef. It’s a Chicago institution.
At O’Hare, if you’re in Terminal 1 or 3, go to Tortas Frontera by Rick Bayless. It is, without hyperbole, the best airport food in the country. The smoked pork torta will make you forget that you just spent two hours on a subway train smelling like old pennies.
Timing Your Trip: The Golden Rules
Chicago weather is a factor. Snow? Add an hour. Heavy rain? Add 45 minutes. A random Tuesday where a ladder fell off a truck on the Dan Ryan? Add two hours.
- The 4-Hour Rule: If your flights are less than four hours apart, do not attempt a self-transfer between Chicago Midway to O'Hare. Between deplaning, getting luggage, traveling, and re-clearing security, you are cutting it way too close.
- TSA PreCheck: It is a lifesaver at O’Hare. The regular lines at Terminal 3 can look like a concert entrance.
- The Night Move: If you’re doing this transfer after 11:00 PM, take an Uber. The Blue Line runs, but headways (the time between trains) can be 20 to 30 minutes, and the platforms can feel pretty lonely.
Actionable Steps for a Smooth Transfer
Check your arrival terminal at O'Hare before you leave Midway. This dictates where you get off the shuttle or the ATS.
Download the Ventra App. You can load a "CTA Single Ride" or "1-Day Pass" directly onto your iPhone or Android wallet. Don't stand in line at the vending machines at Midway; the line is always long and there's always one machine that refuses to take credit cards.
If you choose rideshare, book it as you are walking toward the baggage claim exit. The wait times at Midway fluctuate wildly.
Look at the IDOT (Illinois Department of Transportation) digital signs if you’re in a car. They give "travel times to O'Hare." If the sign says 90 minutes from downtown, believe it. They aren't exaggerating.
If you have a long gap, drop your bags at a luggage storage service (there are a few third-party ones near the Loop) and grab a quick slice of deep dish. Lou Malnati's or Pequod's—everyone has an opinion, but both are better than airport pretzels. Just make sure you’re back on the Blue Line at least two hours before boarding.
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The cross-town transfer is a rite of passage for Midwest travelers. It's rarely fun, but it's manageable if you stop looking at the map and start looking at the clock. Pack light, keep your Ventra card ready, and remember that Tortas Frontera is waiting for you on the other side.