You’re staring at a booking screen, and the price just jumped $40 while you were refilling your coffee. It’s a classic move. If you’re hunting for flights from Chicago to Norfolk VA, you probably know the drill: O’Hare is a mess, Midway is a trek, and Norfolk International is... well, surprisingly easy once you actually get there.
Most people think this is a simple two-hour hop. It is. But if you don't play your cards right with the Chicago-to-Norfolk route, you end up sitting in a middle seat on a regional jet that feels like a flying sardine can.
The Battle of the Hubs: ORD vs. MDW
Honestly, the biggest decision isn't even the airline; it's which side of the city you’re starting from. In 2026, the divide is sharper than ever.
O’Hare (ORD) is where you go if you want options. United and American own this route. United usually runs about 14 nonstop flights a week—basically two a day. American is right behind them. If you’re a miles junkie or you need that 11:05 AM departure to make a 2:00 PM meeting at the Naval Station, O’Hare is your spot. You’ll likely be on an Embraer 175 or an Airbus A319. The Embraer sounds small, but the 2-2 seating means no middle seats. That’s a win in my book.
Midway (MDW) is Southwest territory. Pure and simple. They’re the only ones doing nonstops from Midway to Norfolk (ORF). They usually run two flights a day during the week—one in the morning and one late afternoon—and maybe just one on Saturdays.
The "Southwest Effect" is real here. Since they include two checked bags, the "cheap" $150 flight from Midway often ends up being way less than a "cheap" $110 flight from O'Hare once United tacks on $35 for a suitcase.
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What it Really Costs to Fly to Norfolk
Let’s talk numbers. I’ve seen round-trip fares as low as $131 on United if you book on a Tuesday for a flight three months out. But that’s the dream scenario.
Realistically? You’re looking at:
- The "I Planned Ahead" Price: $260 - $310 round trip.
- The "Last Minute" Sting: $450 - $700. Seriously. If you try to book this on a Friday for a Sunday departure, Norfolk prices get aggressive.
- The Budget Gamble: Spirit and Frontier fly this with stops (usually through Detroit or Orlando). You can find one-way tickets for $46, but you’ll spend 10 hours in transit for a trip that should take two. Is seven hours of your life worth $80? Usually, no.
The sweet spot for booking flights from Chicago to Norfolk VA is about 34 to 86 days out. If you hit that window, you can save roughly 25% compared to the week-of scramble.
Why Sunday is the Worst Day to Fly
Everyone wants to fly home Sunday. Airlines know this. Data from 2024 and 2025 shows that Sunday is consistently 6% to 10% more expensive for this specific route.
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If you can swing a Tuesday or Wednesday departure, do it. Not only is the ticket cheaper, but the security lines at O’Hare Terminal 3 won't make you want to cry.
Navigating Norfolk International (ORF)
Once you touch down, you aren't in Virginia Beach yet. You’re in Norfolk. The airport is about 12 miles from the city center, and if you're heading to the oceanfront, give yourself at least 30-40 minutes depending on the bridge-tunnel traffic.
Ground transportation is pretty standard. Uber and Lyft have dedicated zones between Crosswalks 1 and 2 outside the Arrivals Terminal. If you’re renting a car—which you probably should if you’re visiting the 757 area—the counters are right there.
Pro tip: Norfolk is a massive military town. If you’re flying in on a Thursday or Friday, the airport gets flooded with Sailors and their families. It’s high energy, but it can make the baggage claim area feel like a mosh pit.
Direct Flight Logistics
For those who just want the facts, here is the current 2026 layout:
- United Airlines: Mostly departs from Terminal 1 at ORD. Uses the Boeing 737-800 or A319. Flight time is about 2 hours and 15 minutes.
- American Airlines: Usually T3 at ORD. They love the CRJ-700 or Embraer 175 for this route.
- Southwest Airlines: Midway only. They use the 737 MAX 8 quite a bit on this leg now.
Actionable Steps for Your Trip
Don't just click "buy" on the first Expedia result.
First, check the Southwest Low Fare Calendar. Since Southwest doesn't show up on Google Flights or Kayak, you're missing a huge chunk of the market if you don't look there separately.
Second, if you're flying O’Hare, check which terminal your airline is using. United and American are in different spots, and the walk is longer than you think.
Finally, if you’re carrying more than a backpack, do the math on the baggage fees before you commit to a legacy carrier. That "Basic Economy" ticket on United doesn't even allow a carry-on bag in the overhead bin. You'll get flagged at the gate and charged a premium.
Lock in your flight at least 5 weeks out, choose the 2-2 seating on the Embraer if you value your personal space, and avoid the Sunday afternoon rush if you want to keep your sanity—and your money.