Madison to Chicago flight
Flights from Madison to Chicago start at €31.41 and take 3h 50m at their fastest.
The Flights from Madison to Chicago starts at €31.41 and takes 3h 50m door to door, run by 6 operators over 204 km, with around 48 departures a day. Fares bottom out about 60 days before departure.
- 3h 50mDoor to door
- 40mMoving
- €31.41From
- 50.2 kgCO2
The cheapest and the fastest on September 29, 2026
Two journeys we can sell today, with the service number each operator files them under.
No bookable itinerary on the day this page prices, so none is shown.
Airlines
Speed, flexibility and what is on board. Nothing here is a rating, because we have not earned one.
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When to book Madison to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €11.1890 days
- €10.0760 days
- €10.6345 days
- €11.7330 days
- €13.3821 days
- €14.4814 days
- €16.137 days
- €17.783 days
- €21.081 days
- Cheapest lead time
- Fares bottom out around 60 days ahead, at €10.07.
- How much it moves
- The gap between the cheapest and most expensive lead time is 109 percent. The most expensive point is €21.08, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 60 days before departure. Waiting from here has usually cost money on this corridor rather than saved it.
Which departure day costs least
Median cheapest fare for each weekday, taken across the next three weeks of real prices.
- €14.48Sun
- €12.83Mon
- €12.83Tue
- €13.38Wed
- €14.48Thu
- €15.58Fri
- €15.58Sat
Where you leave from and where you arrive
The stations, airports and ports each mode on this corridor actually uses.
Madison
- MSN
Chicago
- ORD
- MDW
What the journey actually looks like
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
- How far it really runs
- The route covers 204 km against 198 km in a straight line, a detour of 2 percent. Track and road geometry account for the difference.
- First and last departure
- The first service of the day leaves Madison at 06:11 and the last at 20:53, across 48 departures. The return direction keeps its own timetable, so the times back are not these times reversed.
Flights against the other ways to make this journey
The same corridor, door to door, with every mode that runs it.
| Mode | Door to door | Moving | At the ends | From | CO2 | Per day |
|---|---|---|---|---|---|---|
| Train | 2h 9m | 1h 25m | 44m | €26.74 | 6.5 kg | 12 |
| Coach | 3h 25m | 2h 41m | 44m | €12.83 | 5.3 kg | 12 |
| Flight | 3h 50m | 40m | 3h 10m | €31.41 | 50.2 kg | 48 |
Questions about Madison to Chicago
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.
How long does the Flight from Madison to Chicago take?
The Flight from Madison to Chicago takes 3h 50m door to door, of which 40m is spent moving. The route runs 204 km. The difference between the two times is reaching the terminal and leaving it at the far end, which every time on this page includes.
How much does the Flight from Madison to Chicago cost?
The Flight from Madison to Chicago starts at €31.41 for one passenger, checked on September 29, 2026. A typical fare is €31.41. Both are the total including taxes, supplier fees and our service fee, so the price here is the price at checkout.
Who runs the Flight from Madison to Chicago?
6 operators run the Flight from Madison to Chicago: American Airlines, GoJet Airlines, SkyWest, United Airlines, Republic Airways. Between them they file around 48 departures a day. The operator table on this page compares them on fare, journey time, cruising speed, fare conditions and what is provided on board.
Which terminal does the Flight from Madison to Chicago use?
The Flight from Madison to Chicago leaves from Madison MSN and arrives at Chicago ORD. Allow about 3h 10m for reaching the departure terminal and leaving the arrival one. That time is already inside every door to door figure quoted on this page.
Is the Flight the best way from Madison to Chicago?
Traveling from Madison to Chicago by Train costs €26.74 and takes 2h 9m door to door, against 3h 50m by Flight. Which is better depends on whether the money or the hours matter more on this trip. The comparison table on this page shows every mode side by side.
When should I book the Flight from Madison to Chicago?
Fares for the Flight from Madison to Chicago bottom out around 60 days ahead, at €10.07. The gap between the cheapest and most expensive lead time across the window is 109 percent, measured on September 29, 2026. Booking inside the final week has consistently cost more.
How much CO2 does the Flight from Madison to Chicago produce?
The Flight from Madison to Chicago produces about 50.2 kg of CO2 per passenger over 204 km, which works out at roughly 246 grams per passenger kilometer. That figure is for the whole journey and for one traveler, not for the vehicle.
Where these numbers come from
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
- On this page
- Every figure above was computed for Madison to Chicago on September 10, 2026: 204 km of route against 198 km in a straight line, 48 services a day, 6 operators, a cheapest fare of €31.41, and 3h 50m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.