Look, let’s be honest. If you’re trying to book flights to Chicago from Jackson MS, you probably just want a quick nonstop, a bag of pretzels, and to be on your way. But there’s a catch. Most travelers think they can just hop on a direct flight and be in the Windy City in two hours.
The reality? As of January 2026, finding a direct route from Jackson-Medgar Wiley Evers International (JAN) to either O’Hare (ORD) or Midway (MDW) is a bit of a hunt. Most of the time, you're looking at a layover. But that’s not necessarily a bad thing if you know how to play the system.
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The Layover Game: Where You’ll Actually Land
You’ve got options. Southwest, Delta, and American are the big players here. If you’re a Southwest loyalist, you’re almost certainly heading to Midway. It’s smaller, closer to downtown, and generally less of a headache to navigate than O’Hare.
Most people just click the first flight they see. Big mistake.
- The Atlanta Connection: Delta is going to try to funnel you through ATL. It’s the world’s busiest airport for a reason.
- The Charlotte/Dallas Pivot: American Airlines usually routes you through Charlotte or DFW.
- The Nashville Shortcut: Sometimes, you can find a BNA connection. It’s often the shortest total travel time, around 4.5 hours if the stars align.
Honestly, Midway (MDW) is the local favorite for a reason. You can walk from one end of the terminal to the other in about 30 minutes. If you land at O'Hare (ORD), prepare for the "O'Hare Hike." It's massive. If your gate is in Terminal 5 and you need to get to the Blue Line train, you better have your walking shoes on.
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Price Tags and Timing
How much is this going to cost you? Generally, you’re looking at anywhere from $150 to $350 for a round trip if you book a few weeks out.
If you're seeing prices north of $500, you’re likely looking too late or trying to fly during a peak festival weekend (avoid Lollapalooza dates if you want to keep your wallet happy). Data from the Airlines Reporting Corporation suggests that Thursdays are usually the cheapest days to actually fly, while booking on a Sunday can surprisingly save you about 6-13% compared to booking on a Friday.
Navigating JAN Before You Leave
Jackson-Medgar Wiley Evers isn't exactly a sprawling metropolis of an airport. It’s manageable. You can usually get through security in under 15 minutes, but don't push your luck on a Monday morning.
Pro Tip: If you're taking an Uber or Lyft to JAN, have them drop you at the top level. It’s just easier.
Once you’re through security, there’s not a ton to do. Grab a coffee, charge your phone, and double-check your gate. Most flights to Chicago from Jackson MS will depart from Terminal A or B.
When You Land: ORD vs. MDW
So, you’ve arrived. Now what?
O’Hare (ORD) is a beast. If you're staying in the Loop, take the Blue Line train. It’s about five bucks and takes 45 minutes. A taxi or Uber can cost you $60+ and take twice as long if the Kennedy Expressway is backed up—which it always is.
Midway (MDW) is the "life hack" airport. The Orange Line train is right there. It’s a 25-minute ride to the city. It’s cleaner, faster, and much harder to get lost in.
Why the Season Matters
Chicago in January is... well, it's Chicago in January. It’s cold. Really cold.
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But that’s when the flights are cheapest. February is often the rock-bottom month for fares. If you want the best weather, June and September are the sweet spots, but expect those ticket prices to jump by at least 20%.
Actionable Steps for Your Trip
Stop overthinking and just do this:
- Track the flight now. Use a tool like Google Flights or Expedia to set a price alert.
- Aim for Midway. If the price is within $30 of an O'Hare flight, take the Midway one. The time saved on the ground is worth more than thirty bucks.
- Check the layover time. Anything under 45 minutes in Atlanta or Charlotte is a gamble you probably don't want to take.
- Download the airline app. This sounds basic, but in 2026, paper boarding passes are basically relics. The app will tell you if your gate changes before the airport screens do.
Skip the Sunday afternoon return flights if you can; they are the most expensive and the most crowded. Grab a Monday morning flight back to Jackson instead, and you'll likely have a row to yourself.