You’re basically just getting settled into your seat when the pilot announces the descent. That’s the reality of the flight from Memphis International (MEM) to Chicago. Whether you’re landing at O’Hare (ORD) or Midway (MDW), the actual time in the air is usually about an hour and twenty minutes. It’s short. It's fast. Yet, somehow, finding affordable plane tickets Memphis to Chicago can feel like trying to solve a Rubik's Cube in the dark.
Prices swing wildly. One day you’re looking at a $114 round-trip on United, and the next, Southwest is asking for $400 because there’s a convention at McCormick Place you didn't know about. Honestly, it’s annoying. But if you understand how this specific corridor works, you can stop overpaying for a flight that’s shorter than most movies.
The Battle Between O’Hare and Midway
Chicago is a two-headed beast. You have O'Hare, which is a massive, sprawling city unto itself, and Midway, which is more compact and closer to downtown. When searching for plane tickets Memphis to Chicago, your choice of airport dictates which airline you’ll fly.
United and American Airlines own the Memphis-to-O'Hare route. They run regional jets—mostly Embraer 175s or CRJ-900s—back and forth all day long. If you have a connection to Europe or Asia, you're going to O'Hare. Period. On the flip side, Southwest is the king of Midway. They usually run two or three non-stops a day from Memphis.
Don't just look at the ticket price. Look at the "Uber Factor." A cheap flight to O'Hare can be eaten alive by a $60 rideshare to the Loop if you land during rush hour. If you’re staying on the South Side or just want a quicker exit from the terminal, Midway is almost always the better bet, even if the ticket costs twenty bucks more.
The Truth About "Budget" Carriers
We used to have more options. Spirit and Frontier dip in and out of the Memphis market like they're testing the waters. Currently, the "big three" (United, American, Southwest) dominate this specific leg. You might find a weird connecting flight through Charlotte or Atlanta on Delta for a low price, but why would you turn a 90-minute hop into a six-hour odyssey? It's rarely worth the $40 savings.
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When to Pull the Trigger on Your Seats
Timing is everything, but the "Tuesday at 3 AM" rule is a total myth. Airlines use sophisticated AI (ironic, right?) to price seats based on demand. For Memphis to Chicago, the sweet spot is generally 21 to 35 days out.
If you see a fare under $150 round-trip, buy it. Seriously. Don't wait for it to hit $99. It might, but it probably won't.
Monday mornings and Friday afternoons are the "business tax" times. This is when consultants and corporate types are moving between the FedEx headquarters in Memphis and the financial hubs in Chicago. They don't care about the price because their company is paying. You, however, should care. If you can fly on a Tuesday, Wednesday, or Saturday, you’ll often see the price of plane tickets Memphis to Chicago drop by 30% or more.
Logistics That Actually Matter
Memphis International has changed a lot. The new B Concourse is sleek, but it's a long walk. If you're flying American or United, give yourself time. If you're flying Southwest, you're still in that older section of the terminal that feels a bit more "classic Memphis."
Parking vs. Lyft
Parking at MEM is actually decent compared to other cities. The economy lot is $9 a day. If you’re going to Chicago for a long weekend, it’s cheaper to park than to take two Ubers from Germantown or Collierville.
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The Winter Factor
Chicago winters are no joke. Neither are Memphis ice storms. If you're traveling between December and March, check the equipment. United and American fly smaller planes on this route. These regional jets are more susceptible to weight and balance issues or de-icing delays than the big 737s Southwest flies. If the forecast looks nasty, the Southwest flight to Midway is statistically more likely to actually take off.
Why the Price Fluctuates So Much
It’s about "load factor." Since the planes on this route are relatively small (often 76 seats), it only takes a small group of people booking at once to spike the price. A high school band trip or a corporate retreat can wipe out the "Economy Light" fare bucket in minutes.
Also, watch out for Lollapalooza, the Chicago Marathon, or any home game for the Cubs or Bears if they're playing a popular opponent. Those events don't just fill up hotels; they jack up the price of plane tickets Memphis to Chicago weeks in advance.
Baggage Fees and the "Basic Economy" Trap
United and American love their Basic Economy fares. They look great on Google Flights. Then you realize you can't bring a carry-on bag. For a short trip to Chicago, you probably only need a backpack, but if you need a real suitcase, that $130 fare just became $190.
Southwest still gives you two bags free. Even if their base fare looks higher, do the math. If you're heading up to Chicago for a week and need a heavy coat and boots, Southwest almost always wins on total cost.
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How to Monitor Fares Properly
- Google Flights is your best friend. Set a price alert for your specific dates.
- Check Southwest separately. Their data doesn't show up on Google Flights or Expedia. You have to go to their site. It’s a pain, but it saves money.
- Use the 24-hour rule. By law, you can cancel any flight within 24 hours of booking for a full refund (as long as you’re booking at least a week out). If you buy a ticket and the price drops two hours later, cancel and re-book.
Beyond the Ticket: Getting to the City
Once you land, the flight is over, but the travel isn't.
From O’Hare: The Blue Line "L" train is $5. It takes about 45-50 minutes to get to the Loop. It’s cheap, it’s reliable, and it bypasses the nightmare that is the Kennedy Expressway.
From Midway: The Orange Line is your go-to. It’s faster than the Blue Line—usually about 25 minutes to downtown.
If you insist on a taxi or Uber, be prepared. Chicago traffic can turn a 20-mile drive into a two-hour test of patience.
Actionable Steps for Your Next Trip
Stop endlessly refreshing your browser and take these steps to lock in the best deal:
- Check the Hubs: First, go to United.com and see the baseline. United runs the most frequent service, so they set the "market rate."
- The Southwest Comparison: Open a second tab for Southwest. If the price is within $30 of United, go with Southwest to avoid potential baggage fees and for better flexibility with changes.
- Avoid the Regional Trap: If you're tall, look at the plane type. If it’s a CRJ-200 (rare now, but they pop up), avoid it. Your knees will thank you. Stick to the E-175s or Boeing 737s.
- Book Mid-Week: Aim for a Wednesday departure and a Tuesday return if your schedule allows. This is statistically the cheapest way to fly this route.
- Download the Apps: Both the MEM and ORD/MDW apps are surprisingly helpful for real-time gate changes, which happen constantly in Chicago due to weather.
Finding plane tickets Memphis to Chicago doesn't have to be a headache. Just remember that in this specific market, the "cheapest" ticket on the screen is rarely the cheapest one by the time you actually reach your hotel. Look at the total cost of transport, bags, and time. Chicago is a world-class city; don't waste your budget before you even get there.