So here’s the thing—I was sitting in my Austin apartment last January, video chatting with my friend Marcus in Chicago, and I could literally see his breath fogging up the screen. He was wearing two hoodies indoors. TWO. And he said something that I’ve heard from at least a dozen Chicagoans over the years: “I need to get out of here before I lose my mind.”

Three days later, Marcus was sending me photos from Venice Beach in a t-shirt and sunglasses. Total flight cost? $127 round trip.

Look, I get it. The Chicago to LA route is one of those flights that everyone needs at some point. Maybe you’re escaping the polar vortex, visiting family, chasing job opportunities, or just really craving authentic street tacos in the sun. I’ve flown this route probably eight times myself—from both O’Hare and Midway—and I’ve paid everywhere from $89 to (embarrassingly) $340 for basically the same seat.

After years of tracking this route and making pretty much every mistake possible, I’ve figured out how to consistently snag those cheap fares. And honestly? It’s not as complicated as the travel “experts” make it sound.

The Tale of Two Airports (And Why It Actually Matters)

Here’s where Chicago gets interesting. You’ve got O’Hare, which is massive and handles most of the major carriers, and then there’s Midway, which is smaller, closer to the Loop, and primarily serves Southwest and a handful of other budget airlines.

I used to be an O’Hare snob. Bigger airport, more options, right? But then I missed a $98 Southwest fare from Midway because I was stubbornly filtering for only O’Hare flights. That mistake cost me an extra $160. Trust me, the 30-minute difference in getting to either airport is not worth paying double.

Southwest dominates the Midway to LAX route, and they’ve got multiple daily flights. The cool thing about Southwest—and this is something I tell everyone—is their prices can actually drop after you book. If you check back and find a cheaper fare, they’ll give you the difference as travel credit. I’ve literally gotten $40-70 back this way multiple times. It’s like a little treasure hunt after you’ve already booked.

From O’Hare, you’re looking at United, American, Alaska, and Spirit mainly. United and American run this route like it’s a commuter flight, with departures pretty much every hour during peak times. I once counted 15 direct flights between 6 AM and 10 PM on a random Tuesday. The competition is fierce, which works in your favor if you know when to pounce.

The Pricing Sweet Spot (That Nobody Talks About)

Okay, let me share something that took me way too long to figure out. Most travel blogs will tell you to book flights 6-8 weeks in advance. That’s fine advice, I guess, but it’s also super generic and kind of useless for this specific route.

The Chicago-LAX corridor is different because it’s both a business route and a leisure route. Business travelers book last-minute and pay whatever, which actually creates these weird pricing patterns where you can sometimes find better deals closer to departure than months out. Weird, right?

I’ve found the actual sweet spot is usually 3-5 weeks before departure for leisure travel. I tested this theory religiously for about six months last year—checking prices for the same routes at different booking windows—and the 3-5 week range beat the 6-8 week window about 65% of the time. Not scientific, but pretty consistent.

Here’s the other thing: Tuesday and Wednesday flights are usually cheaper, but not always. I know everyone says “fly on Tuesday,” but I once paid $234 for a Tuesday flight while the Saturday flight was $129. The day that actually matters more is when you’re searching. I clear my cookies, use incognito mode, and I’ve noticed Tuesday afternoons and Saturday mornings tend to show the best fares. Could be coincidence, but it’s worked often enough that it’s part of my routine now.

My Favorite Sneaky Strategy (The Positioning Flight Trick)

This is kind of advanced, but it’s saved me hundreds of dollars on the Chicago to LA route specifically. Sometimes—and bear with me here because this sounds backwards—it’s cheaper to fly Chicago to Vegas or Phoenix, then hop another cheap flight to LA, than it is to fly direct.

I discovered this by accident when I was trying to visit my sister in LA but flights were running $380 for some reason (holiday weekend, probably). I checked Spirit flights to Vegas out of curiosity and found them for $60. Then a Frontier flight Vegas to LA for $39. Total cost including fees? $147, versus $380 direct. Yeah, it added four hours to my travel day, but I saved $233 and honestly, I grabbed lunch at the Vegas airport food court which was… fine.

I don’t do this every time because, let’s be real, it’s kind of annoying. But when direct flights are unreasonably expensive and I’ve got time flexibility, this trick is gold. The key is making sure you’ve got at least 2-3 hours between flights in case anything runs late, and booking them as separate tickets means you’re on your own if something goes wrong. I learned that the hard way when a storm delay in Denver almost ruined my connecting plans (that’s a story for another time).

The Real Deal on Budget Airlines

Spirit and Frontier fly this route, and people have Strong Opinions about them. I’ve flown both multiple times between Chicago and LA, so let me give you my honest take.

Spirit gets a bad rap, but for a four-hour flight? It’s totally fine. The seats are thin and don’t recline much, there’s no free snacks or drinks, and you’ll pay for literally everything including a carry-on. But here’s the thing—if you pack light with just a personal item that fits under the seat, the base fare can be absurdly cheap. I once flew Spirit from Midway to LAX for $67 including taxes. The seat was uncomfortable, sure, but I’m 5’6″ and I brought a good podcast. Four hours later, I was in California and my wallet was barely lighter.

Frontier is similar but slightly better in my experience. The seats are a tiny bit more comfortable, and their loyalty program is actually decent if you fly them regularly. I will say both airlines are strict about bag sizes and fees, so read the fine print. I watched someone pay $99 at the gate for a bag that was two inches too big. Don’t be that person.

The major carriers—United and American—obviously offer more amenities and comfort. If you’ve got airline status or prefer a more traditional flying experience, they’re solid choices. Their prices for this route are usually $50-100 more than the budget airlines, but you get free carry-ons, seat selection, and generally more legroom. Alaska is kind of the middle ground—decent prices, good service, and their credit card benefits are pretty nice if you’re into that.

Timing Your Escape (And What Actually Moves Prices)

The conventional wisdom about avoiding peak travel times is mostly true, but LA has some specific quirks. Spring break, Thanksgiving week, and Christmas are obviously expensive—I’m talking $400+ round trip even if you book early. But there are also some less obvious expensive periods.

June weddings. Seriously. LA is a huge wedding destination, and I’ve seen prices spike randomly in mid-June because apparently everyone gets married then. Same with early October—film festival season, fashion events, all that industry stuff that fills up flights.

The cheapest times I’ve found are usually late January through early March (after the holidays, before spring break), and September through early November (after summer, before Thanksgiving). I flew for $118 round trip in mid-February last year, and the flight was maybe 60% full. It was glorious—empty middle seats, smooth boarding, no stress.

Weather can mess with Chicago flights though, especially in winter. I once had three different O’Hare flights canceled in one week due to snow and ice. This is where flying from Midway can actually be clutch—it’s smaller, so they clear it faster, and Southwest has a pretty good track record of keeping flights moving. Not always, but better than I expected.

The Tools I Actually Use (No Affiliate Links, I Promise)

I’m not going to overwhelm you with 47 different apps and websites. Here’s what I personally use for this specific route:

Google Flights is my starting point, always. The calendar view that shows price variations across different dates is perfect for finding those cheap days. I set up price alerts for Chicago to LA and usually get useful notifications at least once a month. Sometimes they’re false alarms, but I’ve also caught fares under $100 that way.

Southwest’s own website for Midway flights, obviously, since they don’t show up on most search engines. I check their sales every Tuesday, which is when they typically drop new deals. Not always relevant to LA, but often enough to be worth a quick look.

Scott’s Cheap Flights (now called Going) has caught some genuine mistake fares on this route. I’m talking like $200 round trip in premium economy kind of deals. They’re rare, but they happen. I pay for the premium membership ($50/year) and it’s paid for itself several times over.

Here’s something kind of old school—I follow all the airlines that fly this route on Twitter. They sometimes post flash sales there before anywhere else. I snagged a $94 one-way on United that way last summer. Was it worth following corporate Twitter accounts? For $94 to LAX, absolutely.

Making It Work For You

Look, I’ve probably overthought this route more than any sane person should. But that’s kind of what I do—I obsess over flights so you don’t have to.

The bottom line is this: Chicago to LA is one of the most competitive routes in the country, which means deals are out there pretty much constantly. You just need to be a little flexible, a little patient, and willing to check both airports. Sign up for alerts, check prices regularly but not obsessively, and don’t panic book the first thing you see.

And honestly? Even if you end up paying $200 for a round trip, you’re still getting four hours of flight time to one of the best cities in the country. Sometimes I think we get so caught up in finding the absolute cheapest fare that we forget the actual goal is just getting to California.

Marcus, by the way, has flown to LA three more times since that January escape. He’s gotten pretty good at finding deals himself now, though he still texts me screenshots to confirm before booking. Last I heard, he paid $103 round trip in September.

The weather in Chicago is probably terrible right now. The weather in LA is probably 72 and sunny. You know what to do.

Safe travels, and may your flights be cheap and your middle seats stay empty.

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