Compare trains, buses, flights and ferries from Jackson to Chicago. From €110.18, fastest 4h 59m, with the total price and every fee shown up front.
Traveling from Jackson to Chicago costs €110.18 at the cheapest and takes 4h 59m door to door at the fastest, across 1 mode and 1 operator. The route covers 1,118 km. Cheapest is by Flight, fastest is by Flight.
Journey times below are door to door, so they include getting to the terminal and away from it at the other end. Fares are the cheapest we currently sell on September 29, 2026.
| Mode | Door to door | Moving | At the ends | From | CO2 | Per day |
|---|---|---|---|---|---|---|
| Flight | 5h 5m | 1h 55m | 3h 10m | €112.24 | 275.0 kg | 4 |
Two journeys we can sell today, with the service number each operator files them under.
Changes at Birmingham, with 92 minutes between services and a walk of about 14 minutes.
Door to door 11h 7mCO2 246.1 kgChanges 1Fixed, no changes
Door to door 5h 5mCO2 275.0 kgChanges 0Fixed, no changes
Live from the operators' own published timetables, through the open transit feeds they publish. Times and services are real. Fares are modeled until our booking connectors are live.
Live from the operators' own published timetables, through the open transit feeds they publish. Times and services are real. Fares are modeled until our booking connectors are live.
Live from our own engine, refreshed on every request. The cheapest days for each way of traveling are marked.
| Cheapest fare by mode and day for Jackson to Chicago | ThuSep 10 | FriSep 11 | SatSep 12 | SunSep 13 | MonSep 14 | TueSep 15 | WedSep 16 | ThuSep 17 | FriSep 18 | SatSep 19 | SunSep 20 | MonSep 21 | TueSep 22 | WedSep 23 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Flight | €244.99 | €235.55 | €243.81 | €160.03 | €144.69 | €138.20 | €136.43 | €156.49 | €138.20 | €151.77 | €175.37 | €139.38 | €144.10 | €112.24 |
| Coach | €275.73 | €220.73 | €176.18 | €193.23 | €161.88 | €180.03 | €125.03 | €170.13 | €170.13 | €161.88 | €153.08 | €131.63 | €117.88 | €119.53 |
Cheapest day: 2026-09-29 · €110.18
That is the traveling done. What happens after you walk out into Chicago is not something we sell.
The search opens on Chicago with your nights already filled in, so it is one step to a real price.
Search Chicago on Booking.comOr compare on Expedia
Partner links. We do not sell accommodation. We earn a commission when a booking completes, and it never changes what you pay.
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
Book now Fares on this route are lowest around 60 days ahead. You are inside that window.
Median cheapest fare for each weekday, taken across the next three weeks of real prices.
The same journey priced on the fifteenth of each of the next six months.
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
The stations, airports and ports each mode on this corridor actually uses.
Speed, flexibility and what is on board. Nothing here is a rating, because we have not earned one.
| Operator | From | Fastest | Typical speed | Flexibility | On board |
|---|---|---|---|---|---|
 Southwest Airlines | €112.24 | 4h 59m | 740 km/h | Fixed fare | Not published |
Every part of the total, so the number at checkout is the number here.
| Part | Amount | Share |
|---|---|---|
| Operator fare | €97.00 | 88% |
| Taxes | €9.70 | 9% |
| Supplier fees | €1.49 | 1% |
| Our service fee | €1.99 | 2% |
| Total you pay | €110.18 | 100% |
A day in Chicago hauling a suitcase is a shorter day than it needs to be. We do not store bags.
Most of the points near Chicago Union Station open before the first train and close after the last one.
Check Chicago on StasherOr try Bounce
Partner links. We do not run these networks. We earn a commission on a booking, and the price is the same as going direct.
The questions people actually ask about this trip, answered from the same prices and times the page above is built on rather than written once and left to go stale.
The fastest journey from Jackson to Chicago takes 4h 59m door to door, of which 1h 55m is spent moving, on the Flight. Most services take around 5h 6m, because that average includes slower stopping services and journeys with a connection. Times include reaching the terminal and leaving it at the far end.
The cheapest fare from Jackson to Chicago is €110.18, checked on September 29, 2026. A typical fare across the next three weeks is €145.28. Both figures are the total for one passenger, including taxes, supplier fees and our service fee, so nothing is added at checkout.
The cheapest way from Jackson to Chicago is by Flight, at €112.24 for one passenger on September 29, 2026. That journey takes 5h 5m door to door. Cheaper is rarely faster on this corridor, and the comparison table on this page shows what each mode costs against what it saves.
Fares from Jackson to Chicago bottom out around 60 days before departure, at €92.18. Across the whole booking window the gap between the cheapest and the most expensive lead time is 166 percent, measured on September 29, 2026. Booking inside the last week has consistently cost more on this corridor.
Wednesday is the cheapest day to depart from Jackson to Chicago, at €114.58. That is the median of 21 priced departure days across the next three weeks, checked on September 29, 2026. Shifting a departure by one day is usually worth more than shifting the booking by one week.
February is the cheapest of the next 6 months to travel from Jackson to Chicago, at €77.43 for one passenger. Each month is priced on its fifteenth, so the comparison is like for like rather than a mix of weekends and midweek departures.
1 operators sell services from Jackson to Chicago across 1 modes: Southwest Airlines. Journey times, fares and fare conditions differ between them, and the operator table on this page compares all of them on speed, flexibility and what is provided on board.
20 percent of the services we sell from Jackson to Chicago are direct. The rest connect at Louisville, Birmingham, Atlanta, Nashville, with about 71 minutes between the two services. Both legs are sold on one booking, so a missed connection is rebooked at no charge.
Services from Jackson to Chicago by Flight leave from Jackson JAN and arrive at Chicago MDW. Allow about 3h 10m in total for reaching the departure terminal and leaving the arrival one, which is already included in every door to door time on this page.
0 of the 1 operators we sell from Jackson to Chicago allow a change or a refund. A change on a changeable fare costs €5.00. The operator table on this page names which is which, and the condition is shown again before you pay.
Observed service A carrier record shows this named operator serving this named pair, and we carry that through unchanged.
Schedules, seat counts and fares are generated by our own model until the supplier contracts are signed. Places, coordinates, operators, which operator serves which pair, and every distance are real. We would rather say that on every page than let a modeled number pass for a filed one.
Defined in full at Door to door, Fares, The booking window, Carbon, Distances
The flight is the simple part. What you do once you are in Chicago is somebody else's catalog.
Timed entry, guided walks and half-day trips out of Chicago, with free cancellation on most of it.
See Chicago on GetYourGuideOr browse Viator
Partner links. We do not sell tours or tickets. We earn a commission on a booking, and it never changes the price.
Plan a trip from here
Ask Ori for the same corridor under a different constraint, or for a longer trip that starts on it.