You’re standing at a baggage carousel at O'Hare, looking at your watch, realizing your connection is actually across town at Midway. It happens way more than you’d think. Maybe you scored a cheap Southwest flight out of MDW after landing on a United international haul, or maybe the weather turned O'Hare into a parking lot and you're scrambling for a backup. Whatever the reason, getting from Chicago O'Hare to Chicago Midway is a rite of passage for anyone who travels through the Midwest frequently. It's about twenty-eight miles of some of the most unpredictable pavement in America.
Chicago traffic isn't a joke. It's a living, breathing entity that feeds on your stress.
If you have a three-hour layover, you're honestly playing a dangerous game. Most seasoned Chicagoans will tell you that a four-hour window is the bare minimum for comfort, especially if you have to clear security again. You've got to factor in the "deplaning tax"—that twenty minutes it takes to actually get off the metal tube—and the inevitable wait for a ride-share or the hike to the CTA station.
The Blue and Orange Reality: Using the CTA
If you want to save money and don't mind a bit of a trek, the "L" is your best friend. But it’s a long friend. You’ll take the Blue Line from O'Hare all the way into the Loop, then transfer to the Orange Line to head south to Midway.
Expect to spend about 90 to 110 minutes on this.
The transfer happens at Clark/Lake or Washington/Wells. Honestly, Clark/Lake is usually the better bet because it's a massive hub, but be ready for stairs and elevators that may or may not smell like a basement. You only pay once if you use a Ventra card or your phone's tap-to-pay. It’s the cheapest way to handle the Chicago O'Hare to Chicago Midway trek, costing just five bucks from ORD (though the return from MDW is cheaper because they don't hit you with that airport departure surcharge).
- The Blue Line runs 24/7, which is a lifesaver for those 3:00 AM arrivals.
- Orange Line service stops around 1:00 AM and picks back up around 4:00 AM.
- Expect crowds during rush hour (7:00–9:00 AM and 4:00–6:30 PM). Trying to squeeze a checked suitcase onto a packed Blue Line car at Grand Avenue is a special kind of hell.
Ride-Shares and Taxis: The Kennedy Expressway Gamble
Taking a Lyft or Uber is the default for most, but the price tag varies wildly. On a quiet Tuesday morning, you might pay $60. On a rainy Friday at 5:00 PM? Good luck. You’re looking at $120+ and a two-hour crawl.
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The route usually takes you down I-90/94 (The Kennedy) and then onto I-55 (The Stevenson). These are two of the most congested roads in the United States. If there is a fender bender near the "Spaghetti Bowl" junction downtown, your GPS arrival time will start climbing like a stock market bubble.
Taxis are a solid alternative. Look for the "Lower Level" signs at O'Hare. Unlike ride-shares, which have designated pickup zones (like the O'Hare Transfer House or specific garage floors), taxis are lined up and ready. Ask for a "flat rate" if you can, though most Chicago cabs will just run the meter. Some dispatch services like Flash Cab or Yellow Cab offer better reliability than a random app algorithm when the weather gets nasty.
Coaches and Shuttles
Regional buses used to be more common, but the options have slimmed down. Coach USA (formerly United Limo) used to run a direct shuttle, but services have been inconsistent post-2020. Always check their current schedule online before banking on it. If they are running, it's usually the most comfortable way to go because you don't have to lug your bags through train turnstiles.
Why the Stevenson Expressway (I-55) Changes Everything
Once you clear the downtown Loop area, the vibe changes. The Kennedy is all about skyscrapers and merging lanes; the Stevenson is industrial. This is the home stretch to Midway.
Midway is significantly smaller than O'Hare. This is a massive plus. While O'Hare is a sprawling city-state with its own zip code, Midway is compact. Once you get dropped off, you can usually get through security and to your gate in twenty minutes. This "Midway Efficiency" is the only reason the Chicago O'Hare to Chicago Midway transfer is even remotely feasible for most travelers.
If you find yourself with extra time at Midway, go to Reilly’s Daughter for a drink or grab a Potbelly sandwich. It’s way less chaotic than the food courts at ORD’s Terminal 3.
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What Most People Get Wrong About Timing
I see it all the time on travel forums: "Can I make a 2.5-hour connection between ORD and MDW?"
No.
Well, maybe if you land at 11:00 PM on a Sunday and have no checked bags and a driver waiting at the curb with the engine running. But for the average human? No. You have to account for:
- Taxiing time: O'Hare's runways are miles from the gates. You can land and still be on the plane for twenty minutes.
- Baggage claim: O'Hare is notoriously slow with luggage.
- The "L" walk: The walk from the ORD terminals to the Blue Line station is about ten minutes under the best conditions.
- The transfer: Walking from the Blue Line to the Orange Line in the Loop isn't instant.
If you're coming from an international flight at Terminal 5, add another hour. You have to clear Customs and Border Protection (CBP), wait for your bags, and then take the ATS (the airport train) just to get to the main terminals or the ride-share zone. It’s a lot of moving parts.
Practical Steps for a Stress-Free Transfer
Don't wing this. Chicago is a city of neighborhoods and gridlock.
First, check the "Chicago Traffic" map on Google before you even step off your first plane. If the Kennedy is deep red, the CTA is your only guaranteed timeline. Even if it's slower, it's predictable.
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Second, if you're taking a ride-share, call it while you're still walking toward the pickup zone. O'Hare is huge. By the time you get to the "Rideshare Pickup" sign, your driver might still be ten minutes away in the staging lot.
Third, keep some small bills or a loaded Ventra app. You don't want to be fumbling with a kiosk at the O'Hare station while a line of fifty people forms behind you.
Fourth, if you're really in a bind and have the budget, look into a private car service like Blacklane or a local limo company. They track your flight and wait in the terminal. It’s expensive, but if you’re about to miss a $1,000 flight to Cancun, that $150 car service starts looking like a bargain.
Ultimately, the trek from Chicago O'Hare to Chicago Midway is manageable if you respect the distance. It’s not just a transfer; it's a cross-county journey through the heart of one of the busiest metro areas in the world. Give yourself the gift of time, bring a pair of headphones for the "L," and keep an eye on the clock. You'll make it, just don't expect it to be a breeze.
Check your terminal assignments one last time before you leave the first airport. Airlines occasionally shift things, and the last thing you want is to arrive at Midway only to find out your "backup" flight was actually at O'Hare Terminal 2 all along. Pack light, move fast, and watch the signs.