If you’ve ever booked a flight into O’Hare with a connecting flight out of Midway, you’ve likely felt that sudden, sharp pang of travel anxiety. You look at the map and think, "It's the same city, right? How hard can it be?"
Well. It’s Chicago.
Knowing how far is Midway Airport from O’Hare is only half the battle. The actual mileage is one thing, but the time it takes to traverse the "Loop" or bypass it entirely is a completely different beast. You aren't just moving between two points on a map; you’re navigating one of the most congested traffic corridors in the United States.
Let's break down the numbers, the routes, and the "oh-no" moments you need to avoid.
The Raw Data: Miles and Minutes
Physically, the distance between O’Hare International Airport (ORD) and Midway International Airport (MDW) is roughly 28 to 30 miles if you’re taking the most common highway route (I-294). If you take the scenic route through the heart of the city (I-90/94), it’s closer to 25 miles.
But miles are a lie in Chicago.
✨ Don't miss: Why Palacio da Anunciada is Lisbon's Most Underrated Luxury Escape
In a perfect world—say, 3:00 AM on a Tuesday—you could make the drive in about 35 minutes. In the real world? During a rainy Thursday afternoon at 4:30 PM? You’re looking at 90 minutes to two hours.
Honestly, if you have a layover shorter than four hours that requires an airport swap, you’re living life on the edge. You’ve got to deplane, grab your bags (because they won't transfer themselves between these two hubs), find your transport, sit in traffic, and then clear security all over again at the second airport.
The Three Main Ways to Make the Swap
You basically have three flavors of travel here: the "I have money and no time" option, the "I have time and no money" option, and the middle ground.
1. Rideshare and Taxis (The Tollway Sprint)
Most people default to Uber or Lyft. It’s easy. You follow the signs to the "Rideshare Pickup" zone—which at O’Hare is a bit of a hike to the upper level of the Garage—and wait.
- The Route: Most drivers will take the I-294 South (the Tri-State Tollway). It bypasses the downtown mess but has its own special brand of "construction forever" delays.
- The Cost: Expect to pay anywhere from $50 to $90. If there’s a "surge" because of a snowstorm or a massive convention at McCormick Place, that price can easily double.
- The Catch: Taxis are often sitting right there at the curb, whereas an Uber might be 10 minutes away in a staging lot. Sometimes the old-school cab is faster just for the lack of wait time.
2. The CTA "L" Trains (The Budget Move)
This is for the brave souls who don't mind hauling luggage through turnstiles. There is no direct train between the two. You have to go into the city and come back out.
🔗 Read more: Super 8 Fort Myers Florida: What to Honestly Expect Before You Book
You take the Blue Line from O’Hare into the Loop (downtown). You get off at the Clark/Lake station. From there, you follow the signs (and the elevated tracks) to transfer to the Orange Line, which takes you straight to Midway.
- Total Time: About 1 hour and 30 minutes.
- Total Cost: $5. It’s the cheapest way, hands down.
- Vibe Check: It’s reliable. The train doesn't get stuck in I-90 traffic. But, if you have three suitcases and it's rush hour, you will not be the most popular person on the Blue Line.
3. Private Shuttles
Companies like Coach USA (formerly United Airport Express) used to be the gold standard, but many of these services have become less frequent or switched to private-only bookings post-pandemic. Always check the current schedule before banking on a shuttle. If you can find one, they usually run about $30–$40.
Why the Route Matters (The I-294 vs. I-90 Debate)
When you're looking at how far is Midway Airport from O’Hare, your GPS will give you a choice.
I-294 (The Tri-State): This is the bypass. It’s almost always faster because it avoids the "Jane Byrne Interchange" (formerly the Circle Interchange), which is a legendary bottleneck near downtown. However, I-294 is a toll road. If you’re in a rental car without an I-PASS, be prepared for those annoying "pay by mail" fees.
I-90/94 (The Kennedy and Dan Ryan): This takes you right past the Willis Tower. It’s beautiful. It’s also a parking lot for 18 hours a day. Only take this route if your driver knows a secret or if the tollway is literally closed due to an accident.
💡 You might also like: Weather at Lake Charles Explained: Why It Is More Than Just Humidity
Navigating the "Hidden" Time Sucks
Don't just count the minutes you're in the car.
- Terminal 5 at O'Hare: If you’re arriving on an international flight, you’ll land at Terminal 5. You then have to take the ATS (the airport train) to get to the main terminals or the rental car center. That adds 15–20 minutes.
- Midway Security: Midway is smaller than O’Hare, but the security line can get deceptively long because the terminal is laid out like a giant "T."
- Baggage Claim: If you’re switching airports, you must claim your bags. At O'Hare, that can take 30 minutes on a bad day.
Real-World Advice for the Transfer
I’ve seen people miss flights because they thought 25 miles meant 25 minutes.
If you're landing at 8:00 AM at ORD and your MDW flight is at 11:00 AM, you are in trouble. By the time you get off the plane (8:30) and get your bags (9:00), you are hitting the heart of morning rush hour. You won't get to Midway until 10:30 at the earliest. That leaves you 30 minutes to check bags and clear security.
Not happening.
My Rule of Thumb: Give yourself a five-hour buffer. It sounds like overkill until you’re sitting on the Kennedy Expressway watching the minutes tick away while your Uber driver listens to talk radio.
Actionable Next Steps
- Check the "Kennedy" construction: Before you land, use the plane's Wi-Fi to check Google Maps for red lines on I-90.
- Download the Ventra App: If you’re taking the train (the "L"), having the app ready to pay your fare saves you from fumbling with the kiosks at the O'Hare station.
- Book a "Taxi Direct": Some services allow you to book a flat-rate taxi in advance which can be cheaper than a surged Uber.
- Look at the "Shared Ride" boards: Sometimes you can find other travelers at the taxi stand going to the other airport and split the fare.
The distance is manageable, but the city is unpredictable. Plan for the traffic, but hope for the 3:00 AM clear roads.
Final Insights:
The journey from O'Hare to Midway is a 28-mile trek that bridges two different worlds of Chicago aviation. While the Blue-to-Orange train transfer is the most "local" way to do it, the I-294 tollway remains the fastest vehicle route for those in a hurry. Just remember: in Chicago, we don't measure distance in miles—we measure it in how many podcasts you can finish before you reach your destination.