Milwaukee to Chicago flight
Flights from Milwaukee to Chicago start at €31.41 and take 3h 45m at their fastest.
The Flights from Milwaukee to Chicago starts at €31.41 and takes 3h 45m door to door, run by 5 operators over 138 km, with around 40 departures a day. Fares bottom out about 90 days before departure.
- 3h 45mDoor to door
- 35mMoving
- €31.41From
- 33.9 kgCO2
The cheapest and the fastest on September 27, 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.
Chicago sits on the water, which usually settles which side of town you want to wake up on. Rooms are not ours to sell.
Looking for somewhere to stay in Chicago?
Hotels and apartments near downtown, most of them with free cancellation, on a map that shows what is walkable.
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.
When to book Milwaukee to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €10.0790 days
- €10.0760 days
- €10.0745 days
- €10.0730 days
- €10.0821 days
- €11.7314 days
- €13.937 days
- €16.133 days
- €17.231 days
- Cheapest lead time
- Fares bottom out around 90 days ahead, at €10.07.
- How much it moves
- The gap between the cheapest and most expensive lead time is 71 percent. The most expensive point is €17.23, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 90 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.
- €11.18Sun
- €10.08Mon
- €10.08Tue
- €10.08Wed
- €11.73Thu
- €12.28Fri
- €11.73Sat
Where you leave from and where you arrive
The stations, airports and ports each mode on this corridor actually uses.
Milwaukee
- MKE
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 138 km against 134 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 Milwaukee at 06:16 and the last at 20:48, across 40 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 | 1h 44m | 1h | 44m | €18.49 | 4.4 kg | 12 |
| Coach | 2h 35m | 1h 51m | 44m | €10.08 | 3.6 kg | 12 |
| Flight | 3h 45m | 35m | 3h 10m | €31.41 | 33.9 kg | 40 |
Questions about Milwaukee 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 Milwaukee to Chicago take?
The Flight from Milwaukee to Chicago takes 3h 45m door to door, of which 35m is spent moving. The route runs 138 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 Milwaukee to Chicago cost?
The Flight from Milwaukee to Chicago starts at €31.41 for one passenger, checked on September 27, 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 Milwaukee to Chicago?
5 operators run the Flight from Milwaukee to Chicago: American Airlines, SkyWest, United Airlines, Air Wisconsin, Southwest Airlines. Between them they file around 40 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 Milwaukee to Chicago use?
The Flight from Milwaukee to Chicago leaves from Milwaukee MKE 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 Milwaukee to Chicago?
Traveling from Milwaukee to Chicago by Train costs €18.49 and takes 1h 44m door to door, against 3h 45m 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 Milwaukee to Chicago?
Fares for the Flight from Milwaukee to Chicago bottom out around 90 days ahead, at €10.07. The gap between the cheapest and most expensive lead time across the window is 71 percent, measured on September 27, 2026. Booking inside the final week has consistently cost more.
How much CO2 does the Flight from Milwaukee to Chicago produce?
The Flight from Milwaukee to Chicago produces about 33.9 kg of CO2 per passenger over 138 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 Milwaukee to Chicago on September 10, 2026: 138 km of route against 134 km in a straight line, 40 services a day, 5 operators, a cheapest fare of €31.41, and 3h 45m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.