Last month, I needed to get from DC to Chicago for a friend’s wedding, and my stomach dropped when I saw the prices. $340 for a basic economy seat? For a two-hour flight? I’d rather eat ramen for a week than pay that much for what’s essentially a glorified bus ride in the sky.

But here’s the thing about the DC-Chicago route—it’s one of those corridors where airlines are constantly battling for business travelers, which means if you know where to look and when to pounce, you can find some seriously good deals. I ended up paying $67 roundtrip. Yeah, you read that right. And honestly? It wasn’t even that hard.

Let me walk you through exactly how I did it, plus all the tricks I’ve learned from flying this route probably fifteen times over the past few years.

Why This Route Is Actually Perfect for Budget Hunters

The DC-Chicago corridor is pretty much a goldmine if you’re willing to be slightly flexible. You’ve got three major airports in the Chicago area (O’Hare, Midway, and even Milwaukee if you’re desperate), and two solid options on the DC side (Reagan and Dulles—we don’t talk about BWI for this route, trust me on that one).

What this means in practice is competition. Lots of it. United dominates at both O’Hare and Dulles, but Southwest keeps things interesting at Midway and Reagan. American plays in this space too. When you’ve got that many players fighting over the same passengers, prices tend to behave… let’s say, erratically. And erratic pricing is exactly what we want.

I learned this the hard way back in 2019 when I paid $280 for a last-minute flight and then watched the price drop to $89 literally two days later. That sting motivated me to get way smarter about this particular route.

The Tuesday-Wednesday Pricing Sweet Spot Nobody Talks About

Okay, so everyone knows about the whole “book on Tuesday” thing, right? It’s become such common advice that it’s basically useless now. But here’s what actually works for DC-Chicago flights: checking prices on Tuesday AND Wednesday afternoons, specifically between 2-5 PM Eastern.

I know, I know, that sounds oddly specific. But I’ve tracked this route obsessively (yes, I have a spreadsheet, don’t judge me), and there’s this weird pattern where Southwest in particular tends to release their sale fares on Tuesday afternoons, and then United and American scramble to match or beat them by Wednesday. It’s like watching a very slow-motion price war.

The flight I scored for $67? I found it on a Wednesday at 3:47 PM. I’d been checking every day that week because I knew the wedding was coming up, and suddenly there it was—a Southwest fare from Reagan to Midway that made me literally gasp at my laptop screen. My boyfriend thought something was wrong. Nope, just found a stupidly cheap flight.

Playing the Airport Shuffle Game

Here’s where things get interesting. Most people default to Reagan-O’Hare because it’s the most convenient pairing. Reagan is way easier to get to than Dulles if you’re anywhere near downtown DC, and O’Hare is… well, O’Hare is O’Hare. It’s huge and kind of annoying, but you can get pretty much anywhere from there.

But Midway? Midway is criminally underrated. It’s smaller, less chaotic, and Southwest basically owns the place. If you’re willing to fly Reagan-Midway instead, you’ll almost always find better prices. The catch is that Midway is on Chicago’s south side, so depending on where you’re actually trying to get to, you might need to factor in extra transit time.

I did the math once when I was trying to visit a friend in Evanston. Reagan to Midway was $73, but then I needed to spend $45 on an Uber to get north. Reagan to O’Hare was $115, and the L train to Evanston was like $5. Sometimes the “cheaper” flight isn’t actually cheaper when you zoom out and look at the whole picture.

Dulles to O’Hare can also surprise you, especially if you’re booking further in advance. United likes to run sales on that route because they’re trying to fill their bigger planes. I’ve seen roundtrips for under $100 if you’re booking like six weeks out. The main downside is that getting to Dulles is kind of a pain unless you’re already in the suburbs, and the Silver Line train only goes so far.

The Ridiculous Power of Being Flexible (Even Just a Little)

I used to think being flexible meant being willing to fly at 6 AM or midnight or whatever terrible time nobody wants. And sure, those flights are usually cheaper. But you don’t need to torture yourself that much.

What actually makes a huge difference is being flexible about your actual travel dates by even just 2-3 days. The wedding I mentioned earlier? It was on a Saturday. Most people were probably searching for Friday to Sunday flights. I searched Thursday to Monday and saved probably $150 compared to what everyone else was paying.

Google Flights has this calendar view that shows you prices across different dates, and it’s honestly the first thing I check now. Sometimes shifting your trip by literally one day cuts the price in half. It’s kind of absurd, but airlines price based on demand predictions, and if they think fewer people want to fly on Thursday versus Friday, they’ll drop that Thursday fare like a hot potato.

The other flexibility trick that works surprisingly well for this route is being willing to take a connection. I know, I know—why would you connect on a two-hour direct flight? Because sometimes it’s $100 cheaper, that’s why. I’ve done DC to Chicago via Charlotte before (don’t ask, it was weird), and I paid $58 roundtrip. Did it add three hours to my travel time? Yep. Did I bring a good book and some snacks and save enough money to cover my entire weekend food budget? Also yep.

Scott’s Cheap Flights and Other Fare Alert Magic

Look, I’m not getting paid to say this, but Scott’s Cheap Flights (now called Going, which is a way less fun name) has saved me so much money on this route that it feels illegal not to mention it. I have the free version, and they send me alerts when fares drop below certain thresholds.

A few months ago, they sent me an alert about United having a sale from DC to Chicago for $54 one-way. I didn’t even need to fly anywhere, but I forwarded it to like five friends who were planning trips, and three of them booked. That’s the thing about fare alerts—they tell you when the sales are happening so you don’t have to check manually every single day.

Airfarewatchdog is another good one for this specific route. They’re less polished than Going, but they catch some deals that slip through the cracks. I use both and just deal with the duplicate emails because occasionally one of them will find something the other missed.

The key is to actually book when you see a good deal, though. I’ve made the mistake of thinking “oh, I’ll book tomorrow when I have more time to think about it,” and by tomorrow the fare is back up to $200. These sales don’t last long, especially on popular routes like DC-Chicago.

Credit Card Points Aren’t Just for Fancy People

I used to think travel credit cards were only worth it if you were flying business class to Europe or whatever. Turns out they work great for cheap domestic flights too, especially on this route.

I have the Southwest credit card (the basic one, not the fancy version), and between the signup bonus and the points I rack up from regular spending, I’ve flown DC to Chicago completely free probably four times in the past two years. Southwest points are weirdly valuable for this route because they don’t have blackout dates, and you can cancel for free if you find a cheaper cash price later.

Chase also has this thing where you can transfer points to United, and United sometimes has these saver awards where you can book DC to O’Hare for like 7,500 points one-way. That’s… nothing. That’s so few points that you can earn them pretty much by existing and having a credit card. I used United points to fly to Chicago for a last-minute job interview once, and it cost me zero dollars. Just points I’d accumulated from buying groceries and paying my internet bill.

The trick is to not overcomplicate it. You don’t need seventeen different credit cards and a PhD in points optimization. Just get one or two good travel cards, use them for your normal spending, and bank those points for flights you know you’ll need to take.

When to Just Bite the Bullet and Pay More

Okay, real talk for a second. Sometimes the cheap option is actually the expensive option when you factor in your time and sanity.

Last year, I found a DC-Chicago flight for $43, which sounds amazing until you realize it left at 5:50 AM from Dulles. To catch that flight, I would’ve needed to leave my apartment at 3:30 AM, which meant either not sleeping or paying for an airport hotel the night before. I did the math, and between the Uber to Dulles at that hour, the coffee I’d need to not be a zombie, and the general misery of functioning on zero sleep, I’d basically be paying way more than if I’d just booked the $90 noon flight from Reagan.

There’s also the connection thing I mentioned earlier. A connection can be worth it if it’s saving you serious money and you’ve got time to kill. But if you’re flying for something time-sensitive, or if you’re already exhausted, just pay the extra $50 for the direct flight. Your future self will thank you.

I learned this lesson when I tried to save $70 by connecting through Atlanta on my way to Chicago for a conference. My first flight got delayed, I missed my connection, and I ended up arriving five hours late and missing the entire first day of the conference. The money I “saved” on the flight got eaten up by the hotel night I’d already paid for but didn’t use. Sometimes being cheap is actually expensive.

My Personal Flight-Booking Routine That Actually Works

These days, I’ve got a pretty solid system. About six to eight weeks before I need to fly DC to Chicago, I set up fare alerts on both Going and Google Flights. Then I check prices myself every Tuesday and Wednesday afternoon, usually while I’m pretending to work but actually procrastinating.

I look at Reagan to Midway first because that’s usually cheapest, then Reagan to O’Hare, then Dulles to O’Hare if I’m feeling adventurous. I plug in dates with some flexibility—like if I need to be there on Saturday, I’ll search Thursday through Monday departure dates and see what pops up.

When I find something under $100 roundtrip, I usually jump on it. Under $80? I book immediately without overthinking. I’ve been doing this long enough to know that $80 roundtrip for DC-Chicago is genuinely good, and it’s not likely to get much better.

If I don’t find anything good in that first round of searching, I wait a week and try again. Prices on this route fluctuate like crazy, so what’s $240 today might be $89 next Tuesday.

The absolute key is not getting emotionally attached to specific departure times or dates if you can help it. The people paying $300 for their tickets are usually the ones who need to leave Friday at 5 PM and come back Sunday at 8 PM because they can’t be flexible at all. If you can be even slightly flexible, you’ll consistently pay 50-70% less than they do.

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Trust me on this—flying DC to Chicago doesn’t have to drain your bank account. I’ve done this route enough times that I’ve basically figured out the pattern, and once you know what to look for, finding cheap flights becomes almost automatic. You’ve just got to be willing to check prices at the right times, stay flexible where you can, and pounce when you see a good deal.

And honestly? The satisfaction of scoring a $67 flight while everyone else on the plane paid three times that much never gets old. You’ll get there for way less than you think. Just keep checking those Tuesday and Wednesday afternoon prices, and let me know when you find a ridiculous deal—I’m always curious what other people are finding on this route.

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