You'd think a flight that barely hits the two-hour mark would be a total breeze to book, right? Well, honestly, trying to snag a seat on flights Chicago to Memphis can feel like a weirdly high-stakes game of chess if you don't know which airport to pick or when to pull the trigger on those tickets.
I’ve spent way too much time staring at flight trackers. Most people just hop on a travel site, see a price at O'Hare, and click "buy." But that’s usually where they leave money on the table.
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The ORD vs. MDW Dilemma
First off, let’s talk about the two giants. You’ve got O’Hare (ORD) and Midway (MDW).
If you’re flying out of O’Hare, you’re basically looking at the "big two": American Airlines and United Airlines. They dominate this route. Between them, they run about five nonstop flights a day. It's fast. You're in the air for maybe 1 hour and 50 minutes. Sometimes you're barely at cruising altitude before the pilot starts the descent into the 901.
But then there’s Midway.
Southwest Airlines runs the show over there. If you’re a "two bags fly free" kind of person, MDW is your home base. Interestingly, Southwest actually started moving some operations into O'Hare too, so they’ve got about 40 weekly flights from ORD now. It’s knda changed the landscape.
Frontier also pops up at Midway quite a bit. They’re the ones offering those "too good to be true" $65 or $75 one-way fares. Just remember, they’ll charge you for everything else—even a "hello" if they could.
When to Actually Buy Your Ticket
Timing is everything. People always say "book on a Tuesday," but that's mostly a myth.
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Data for 2026 shows that the real sweet spot is booking about three weeks to a month in advance. If you wait until 14 days out, prices usually spike by about 49%. That’s a massive jump.
- Cheapest Day to Fly: Thursday. Usually, flying midweek (Tuesday or Wednesday) is the rule, but for this specific route, Thursday has been hitting the lowest price points lately.
- Most Expensive Day: Sunday. Everyone is trying to get home or get to work. Avoid it if you can.
- Best Month: August or January. If you can handle the Memphis humidity in August or the Chicago "hawk" wind in January, you’ll save a ton.
The Memphis International (MEM) Reality Check
When you land at Memphis International, don't expect a massive, sprawling labyrinth like O'Hare. They recently did a huge modernization of Concourse B, so it actually feels pretty sleek and easy to navigate now.
Ground transportation is where people get tripped up.
If you’re renting a car—which you basically have to in Memphis because it’s not exactly a "walking city"—the Rental Car Facility is a bit of a trek. You head downstairs to baggage claim and follow the signs.
Be warned: if you're under 25, places like Enterprise or National will hit you with a $25-a-day surcharge. Also, if you’re using a debit card, they are strict. You absolutely must have a ticketed return itinerary or they might ask for a $400 to $850 deposit. I've seen people get stuck at the counter because they didn't have their return flight info pulled up.
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Pricing Nuances You Should Know
A "good" price for a round-trip right now sits somewhere between $160 and $190.
If you’re seeing $300+, you’re likely looking at a peak weekend or a holiday. During spring break (March/April), the average cost climbs to about $341.
Southwest is usually the most reliable for punctuality on this route, hitting about an 81% on-time rate. American and United are close behind, but O'Hare's weather delays are notorious. One snowflake in Des Plaines and your 2:00 PM flight to Memphis is suddenly a 6:00 PM flight.
Actionable Steps for Your Trip
Stop overthinking the "perfect" time and just do this:
- Check Midway first. Even if you live closer to O'Hare, the Southwest or Frontier fares from MDW often justify the extra 20 minutes in an Uber.
- Use a price tracker. Set a Google Flights alert for your dates. If it drops below $175 round-trip, buy it immediately.
- Book the morning flight. The 7:45 AM or 8:10 AM departures are significantly less likely to be delayed by the "ripple effect" of air traffic. Plus, they’re often $50-$60 cheaper than the afternoon slots.
- Have your return flight proof ready. Especially if you're renting a car with a debit card at MEM.
Memphis is a great town, but don't overpay to get there. Stick to the Thursday departures, keep an eye on Midway, and you’ll have plenty of extra cash left over for some actual dry-rub ribs.