You’re standing on the edge of the Chesapeake Bay, looking at a map and realizing Chicago is a solid 800 miles away. It’s a long haul. Most people just pull up a flight search, see the prices for a direct hop from ORF to ORD, and call it a day. But honestly, traveling from Norfolk VA to Chicago IL is one of those routes where the "obvious" choice isn't always the smartest one.
I’ve done this trek. I’ve sat in the bumper-to-bumper nightmare of the Hampton Roads Bridge-Tunnel and I’ve spent way too many hours staring at cornfields in Ohio. There is a specific rhythm to moving from the humid, salty air of Coastal Virginia to the windy, deep-dish-scented streets of the Midwest. Whether you’re moving for a job at Boeing or just hitting up a Cubs game, you have three real options, and they all have some pretty annoying quirks you should know about before you book anything.
The Flying Reality: ORF to ORD (or MDW)
Let’s talk about the air. Norfolk International Airport (ORF) is actually a pretty decent place to fly out of, mostly because it’s small enough that you won't lose your mind in security. To get from Norfolk VA to Chicago IL, you’re usually looking at United or American for those precious non-stop flights.
Non-stops are great. Usually, it's about a two-and-a-half-hour flight. You take off over the water, bank left, and basically cruise over the Appalachians until everything turns into flat, square farmland. But here is the thing: prices fluctuate wildly. Because Norfolk is a military town (shoutout to Naval Station Norfolk), flights can get booked up by government travelers on short notice, driving the "civilian" prices through the roof.
If the direct flights to O'Hare (ORD) are too pricey, check Midway (MDW). Southwest flies there, but you’ll almost certainly have a layover in Baltimore (BWI). It sounds like a hassle, but BWI is basically a Southwest hub, and sometimes that extra hour in Maryland saves you $200. Plus, Midway is much closer to downtown Chicago than O'Hare. If your hotel is in the Loop, you’ll thank yourself when you’re not sitting in an hour of traffic on I-90.
The O'Hare "Trap"
O'Hare is massive. It’s a city. If you land there, don't expect to be out of the airport in twenty minutes. Between the taxi time on the runway and the hike to the Blue Line or the rideshare pickup zone, give yourself an hour of "buffer time" before you tell anyone in Chicago you've "arrived."
The 13-Hour Grind: Driving from Norfolk VA to Chicago IL
Driving is the most common way people handle the Norfolk VA to Chicago IL route, especially if they are moving. It is a beast. You are looking at roughly 800 to 850 miles depending on your exact start and end points.
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Google Maps will tell you it takes 12 hours and 45 minutes. Google is a liar.
Google doesn't account for the fact that West Virginia exists. The most direct route takes you through the mountains. You’ll likely take I-64 West toward Richmond, then hit I-81 North briefly before jumping back on I-64 through the Blue Ridge Mountains. This stretch is gorgeous. It’s also exhausting. You’re dealing with steep grades, semi-trucks that move at 10 mph uphill, and weather that can turn from sunny to "I can't see the hood of my car" in about four minutes.
The West Virginia Factor
Once you cross into West Virginia, the cell service gets spotty. The "Green Bank Quiet Zone" is real—there is a massive radio telescope out there, and they don't want your 5G interfering with the aliens (or whatever they’re looking for). Download your maps. Seriously. If you lose your GPS near Charleston, you’re relying on road signs and intuition, and WV roads are not always intuitive.
After you clear the mountains and hit Ohio, the drive becomes a test of mental endurance. You’ll likely take I-35 up toward Dayton and then I-70 or I-75 to eventually find I-65 or I-90. It is flat. It is gray. It is full of state troopers.
- Pro Tip: Stop in Indianapolis if you need a break. It’s almost exactly the three-quarters mark. The food scene there is surprisingly good (try Milktooth for brunch if you’re passing through in the morning).
- The Tolls: Once you hit Northern Indiana and the outskirts of Chicago, the tolls start. The Indiana Toll Road and the Skyway will eat your lunch. Make sure your E-ZPass is loaded. If you don't have one, you’ll be fumbling for credit cards at every plaza while people behind you honk. It’s not fun.
The Amtrak Option: For the Patient Souls
Nobody ever talks about taking the train from Norfolk VA to Chicago IL, and honestly, I get why. There is no direct train. You can't just hop on at the Norfolk station and wake up at Union Station in Chicago.
You have to take the Northeast Regional up to Washington D.C. (Union Station). From there, you transfer to the Capitol Limited. The Capitol Limited is a legendary route that runs through Harper's Ferry and the Allegheny Mountains. It’s stunning.
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It’s also slow. The whole trip will take you about 22 to 24 hours.
Why would anyone do this? Because driving is stressful and flying is cramped. On the train, you have a massive seat with more legroom than a first-class flight. You can walk to the observation car. You can drink a beer while looking at the Potomac River. If you aren't in a rush, it’s arguably the most "human" way to travel. Just be prepared for delays. Freight trains own the tracks, and Amtrak has to wait for them. If a coal train breaks down in Ohio, you’re going to be sitting there for a while.
Moving Your Life Across the Mason-Dixon
If you’re moving from Norfolk VA to Chicago IL, the logistics get heavier. Norfolk is a city of renters and military families; Chicago is a city of neighborhoods and strict parking permits.
Don’t just hire any moving company. Look for "Interstate Movers" who are registered with the Department of Transportation. Because this is a high-traffic military route, there are a lot of scams. If a quote sounds too good to be true, it probably is.
One thing people forget: Chicago apartments often require a "moving fee" instead of a security deposit. Also, if you’re moving into a high-rise in the Gold Coast or South Loop, you have to reserve the freight elevator weeks in advance. If you show up with a U-Haul and no reservation, the doorman will literally turn you away. It’s brutal.
Weather Shock
You're leaving a place where 30 degrees is a "state of emergency" and moving to a place where -10 degrees is "Tuesday." If you’re making the move in the winter, make sure your car has the right coolant and your tires aren't bald. The "Lake Effect" snow in Chicago is no joke. It’s heavier and more frequent than anything you’ve seen in Tidewater.
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Breaking Down the Costs
Let's get real about the wallet.
If you fly, you're looking at $250 to $500 for a round-trip ticket. Add $50 for parking at ORF and another $60 for an Uber from O'Hare to your final destination.
If you drive, you’re covering 850 miles. At 25 mpg, that’s 34 gallons of gas. At $3.50 a gallon, that’s roughly $120 one way. Add $30 for tolls and $100 for a cheap hotel in Ohio or Indiana if you can’t pull the 13-hour straight shot. Driving is cheaper if you have a passenger to split the cost, but for a solo traveler, the savings over flying are surprisingly slim once you factor in the wear and tear on your car.
What Most People Get Wrong About Chicago
When folks from Virginia head to the Windy City, they expect a big, scary metropolis. And yeah, it’s big. But Chicago is actually a "City of Neighborhoods." It feels much more like a collection of small towns than New York does.
People are generally nicer than you’d expect. They’ll give you directions. They’ll argue about whether a "Chicago Dog" should have ketchup (it shouldn't). Just don't call the Willis Tower by its current name; it will always be the Sears Tower to locals.
The biggest culture shock? The pace. Norfolk has that coastal, slower-moving vibe. People take their time. In Chicago, people are moving. They’re walking fast to catch the "L" train. They’re driving like they’re in a Fast and Furious movie. You have to pick up the tempo.
Actionable Steps for Your Trip
Don't just wing it. If you're planning a move or a long visit from Norfolk VA to Chicago IL, here is your checklist to keep your sanity:
- Check the HRBT status first. If you’re driving, look at the Hampton Roads Bridge-Tunnel cameras before you even put your shoes on. If it’s backed up, take the Monitor-Merrimac (I-664). It adds miles but saves your soul.
- Book the 6:00 AM flight. It sucks waking up that early, but those are the flights least likely to be delayed by cascading issues throughout the day.
- Get a "SpotHero" account. If you’re driving into Chicago, do not try to park on the street. Use the SpotHero app to find a garage. You’ll save 50% on parking rates, which can be as high as $70 a night in the city center.
- Update your E-ZPass. Virginia’s E-ZPass works in West Virginia, Ohio, Indiana, and Illinois. Make sure your credit card on file hasn't expired, or you'll get a fat stack of "Pay by Plate" invoices in the mail three weeks later with added fees.
- Pack layers. Even in summer, the breeze off Lake Michigan can drop the temperature 10 degrees in an hour. It’s called "cooler by the lake," and it’s a very real phenomenon.
The trek from the Atlantic coast to the Great Lakes is a transition between two different Americas. One is rooted in maritime history and Navy gray; the other is built on steel, jazz, and midwestern grit. It’s a long way, but if you pick the right mode of transport and prepare for the mountains, it’s a hell of a ride.