You just landed at Midway. You're tired. Your next flight leaves from O'Hare in four hours, and suddenly, the "easy" transfer you saw on a map feels like a massive mistake. Chicago is a beast of a city when it comes to traffic, and honestly, the distance from Chicago Midway Airport to O'Hare isn't just about miles. It’s about timing, nerves, and knowing which specific highway exit is going to ruin your afternoon.
Chicago is unique because it's one of the few U.S. hubs where you might actually have to swap airports to catch an international connection or a cheaper regional leg. It happens more than you'd think. Southwest dominates Midway (MDW), while United and American rule O'Hare (ORD). If you’re hopping between them, you’re crossing about 30 miles of some of the most unpredictable pavement in the Midwest.
Don't panic. You've got options. But if you choose the wrong one during rush hour, you’re going to be staring at the taillights of a semi-truck while your plane takes off without you.
The Reality of the "Orange to Blue" Train Transfer
Most travel blogs will tell you to take the "L." It’s the cheapest way to get from Chicago Midway Airport to O'Hare, and yeah, it costs about five bucks. But here’s what they don’t tell you: you have to go all the way into the heart of the Loop and then back out.
You start on the Orange Line at Midway. It’s elevated, so you get a decent view of the South Side. You ride that until you hit downtown—usually Clark/Lake or Washington/Wells. Then, you have to schlep your luggage through the station, find the Blue Line, and head toward O'Hare. It’s a grind.
The total time? Budget two hours. Minimum. If it’s winter and the tracks are icy, or if there's a "sick passenger" delay (a classic CTA trope), it could be longer. The Blue Line is also notorious for being crowded. If you have three suitcases and a stroller, your fellow commuters might give you some pretty heavy side-eye. It’s a budget-friendly move, but it’s definitely not the "vacation" move.
Uber, Lyft, and the I-294 Gamble
If you've got the cash, you’re probably thinking about a rideshare. It’s faster, right?
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Maybe.
The route from Chicago Midway Airport to O'Hare usually involves taking Cicero Avenue up to I-55, then hitting I-294 (The Tri-State Tollway). On a Tuesday at 10:00 AM, you might make it in 45 minutes. It’s a breeze. But if your flight lands at 4:30 PM on a Friday? Godspeed. The I-294 corridor becomes a parking lot. I’ve seen that 45-minute drive turn into a two-hour existential crisis.
Expect to pay anywhere from $60 to $120. Surges are real. Also, keep in mind that Midway has a very specific rideshare pickup zone (usually Level 3 of the parking garage). Don’t stand at the arrivals curb looking for your Prius; you’ll be waiting forever while your driver circles the block in frustration.
The "Coach USA" Secret (and Why It’s Gone)
For years, there was a shuttle called Coach USA (Waukesha-Milwaukee-Chicago) that ran directly between the two airports. It was the "gold standard" for this specific transfer.
It’s basically defunct for airport-to-airport transfers now.
A lot of old travel forums still recommend it, but don’t rely on it. Nowadays, if you want a shuttle, you’re looking at private companies like Go Airport Express. The catch? They often wait until the van is full. You could be sitting at the curb for 30 minutes before the wheels even turn. It’s better than the train if you have lots of bags, but it’s rarely faster than a private car.
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Why the Route Matters: Neighborhoods and Navigating
When you’re moving between these two hubs, you’re passing through the literal guts of Chicago. You’ll see the industrial corridors of the South Side, the skyscrapers of the West Loop, and the sprawling suburbs near Rosemont.
If you’re driving yourself—maybe a one-way rental—avoid Cicero Avenue as much as possible. It has a stoplight every block, and they aren't synced. It’s a slow death by red light. Instead, get on the Stevenson (I-55) as fast as you can.
The "Kennedy" Alternative
Sometimes, Google Maps will tell you to take the Dan Ryan (I-94) to the Kennedy (I-90). This takes you right past the Willis Tower. It’s iconic. It’s also usually a trap. The "junction" where all these highways meet is one of the most congested interchanges in the United States. Unless the tollway (294) is literally on fire, stick to the tollway.
Timing Your Connection: The 6-Hour Rule
Let's talk about the math. If you're booking separate tickets and need to go from Chicago Midway Airport to O'Hare, do not—under any circumstances—give yourself less than four hours between landing and takeoff.
Actually, make it six.
Think about it. It takes 30 minutes to deplane and get your bags. It takes 15 minutes to find your ride. It takes 90 minutes to cross the city. Then, you have to check back in at O'Hare, which has some of the longest TSA lines in the country (especially Terminal 3). If you’re switching from a domestic Southwest flight to an international flight at O'Hare Terminal 5, you’re adding even more time because Terminal 5 is physically separated from the rest of the airport. You have to take the ATS (the airport train) just to get to your gate.
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Is it better to just stay the night?
If your arrival at Midway is late in the evening and your O'Hare flight is the next morning, don't try to be a hero. Stay near O'Hare. There are dozens of hotels in Rosemont with free shuttles. Midway’s hotel scene is a bit more industrial and spread out. You’ll sleep better knowing you’re already on the right side of the city when the morning rush hits.
What Most People Get Wrong
The biggest misconception is that Chicago has a "quick" connector. It doesn't. London has the Heathrow Express. Paris has the RER. Chicago has a series of aging highways and a subway system designed in the 1940s.
Another mistake? Assuming a taxi is better than an Uber. In Chicago, taxis have a flat rate "City to Suburb" or "Airport to Airport" surcharge sometimes, but usually, they just run the meter. With traffic, that meter keeps ticking even when you aren't moving. At least with a rideshare, you usually see the price upfront, even if it's high.
Actionable Steps for a Seamless Transfer
- Check the "L" Status First: Before you leave the terminal, open the CTA website or use an app like Transit. If the Blue Line has a major delay, the train is off the table.
- Book Your Ride While Walking to Baggage Claim: Don't wait until you're at the curb. Give the driver those extra minutes to get into the staging area.
- Terminal 5 Factor: If your O'Hare flight is international, tell your driver "Terminal 5." It is not connected to the main terminal loop by road in the same way, and missing that turnoff adds 15 minutes of looping back around.
- Pack a Snack: It sounds silly, but if you’re trapped on I-294 for two hours, you’ll be glad you have water and a granola bar. There are no pit stops on the tollway once you're in the thick of it.
- Use the Tollway: If you are driving, make sure your rental has an I-PASS or E-ZPass. Paying cash at tolls is becoming a thing of the past and creates unnecessary stress.
The trek from Chicago Midway Airport to O'Hare is a rite of passage for many travelers. It’s manageable, but it requires respect for the city's geography. Don't underestimate the "City of Broad Shoulders"—it has a way of holding onto you longer than you planned.
To ensure you don't miss your connection, verify your O'Hare terminal number at least three hours before your scheduled departure, as gates change frequently in Chicago's busy airspace. Keep your boarding pass handy and watch the traffic density on a live map app during your entire transit. Once you arrive at O'Hare, prioritize getting through security before looking for food or amenities, as TSA wait times fluctuate wildly throughout the day.