Cheapest€232.60
- Alaska Airlines AA501317:124h 19m21:31Portland PDXChicago ORD
Door to door 7h 29mCO2 715.4 kgChanges 0Fixed, no changes
Portland to Chicago flight
Flights from Portland to Chicago start at €272.72 and take 7h 16m at their fastest.
Check dates and fares
Fares and seats move by the day. Price Portland to Chicago on the date you actually want, rather than on the date this page was built.
The Flights from Portland to Chicago starts at €272.72 and takes 7h 16m door to door, run by 5 operators over 2,908 km, with around 30 departures a day. Fares bottom out about 30 days before departure.
- 7h 16mDoor to door
- 4h 6mMoving
- €272.72 to €489.84From
- 06:25 to 20:05First and last departure
- 30Per day
- 715.4 kgCO2
First and last are taken from the services we sell on 28 September 2026. The return direction keeps its own timetable and is not these times reversed.
€272.72 to €489.84 for one passenger across the 14 departure dates priced here. The low end is one day, not every day. Worked out from this corridor rather than held for anybody. The operator sets the price on the day.
Fares by date
What this journey usually costs, by departure date. It shows which days run dearer.
Typical fares
- about €489.84Mon14
- about €411.96Tue15
- about €442.64Wed16
- about €457.98Thu17
- about €423.76Fri18
- about €442.05Sat19
- about €397.80Sun20
- about €275.67Mon21
- about €272.72Tue22
- about €298.68Wed23
- about €364.76Thu24
- about €337.03Fri25
- about €344.70Sat26
- about €321.69Sun27
Based on what this route has cost recently. The operator sets the price on the day, and the live fare is confirmed when you book.
The cheapest and the fastest on 28 September 2026
Fastest€253.84
- United Airlines UA877911:414h 6m15:47Portland PDXChicago MDW
Door to door 7h 16mCO2 715.4 kgChanges 0Fixed, no changes
Airlines
| Operator | From | Fastest |
|---|---|---|
 American Airlines | €233.78 | 7h 14m |
 Asiana Airlines | €236.14 | 7h 13m |
| United Airlines | €244.99 | 7h 14m |
 Southwest Airlines | €243.81 | 7h 14m |
 Alaska Airlines | €232.60 | 7h 13m |
The flight gets you into Chicago. It does not get you a bed, and neither do we.
A room in Chicago for the night the flight gets in
Sort by distance from Chicago Union Station and you can see which places are ten minutes on foot and which are not.
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When to book Portland to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €277.4490 days
- €230.2460 days
- €194.8445 days
- €182.4530 days
- €247.3521 days
- €321.6914 days
- €397.807 days
- €442.643 days
- €489.841 days
- Cheapest lead time
- Fares bottom out around 30 days ahead, at €182.45.
- How much it moves
- The gap between the cheapest and dearest lead time is 168 percent. The dearest point is €489.84, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 30 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.
- €321.69Sun
- €275.67Mon
- €272.72Tue
- €298.68Wed
- €364.76Thu
- €337.03Fri
- €344.70Sat
Where you leave from and where you arrive
Portland
Air
- PDX
Chicago
Air
- ORD
- MDW
What the journey actually looks like
- How far it really runs
- The route covers 2,908 km against 2,823 km in a straight line, a detour of 3 percent. Track and road geometry account for the difference.
- First and last departure
- The first service of the day leaves Portland at 06:25 and the last at 20:05, across 30 departures The return direction keeps its own timetable, so the times back are not these times reversed.
Questions about Portland to Chicago
The questions people actually ask about this journey, 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 Portland to Chicago take?
The Flight from Portland to Chicago takes 7h 16m door to door, of which 4h 6m is spent moving. The route runs 2,908 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 Portland to Chicago cost?
The Flight from Portland to Chicago starts at €272.72 for one passenger, as of 13 September 2026. A typical fare is €286.29. 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 Portland to Chicago?
5 operators run the Flight from Portland to Chicago: American Airlines, Asiana Airlines, United Airlines, Southwest Airlines, Alaska Airlines. Between them they file around 30 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 Portland to Chicago use?
The Flight from Portland to Chicago leaves from Portland PDX and arrives at Chicago MDW. 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.
When should I book the Flight from Portland to Chicago?
Fares for the Flight from Portland to Chicago bottom out around 30 days ahead, at €182.45. The gap between the cheapest and dearest lead time across the window is 168 percent, measured on 13 September 2026. Booking inside the final week has consistently cost more.
How much CO2 does the Flight from Portland to Chicago produce?
The Flight from Portland to Chicago produces about 715.4 kg of CO2 per passenger over 2908 km, which works out at roughly 246 grams per passenger kilometre. That figure is for the whole journey and for one traveller, not for the vehicle.
Where these numbers come from
Places, coordinates, operators, which operator serves which pair, and every distance on this page are real and come from open data. Where a corridor has a filed timetable the departure times are real too, and ferry fares are the prices the operators publish themselves.
Observed service A carrier record shows this named operator serving this named pair, and we carry that through unchanged.
Where no operator publishes a fare for a corridor, the price here is our own estimate, worked out from the real distance and the real operator through a fare curve that follows lead time, day of the week and season. It tells you roughly what the journey costs. It is not a seat anyone has agreed to sell, and the payment step will not take it.
Defined in full at Door to door, Fares, The booking window, Carbon
- On this page
- Every figure above was computed for Portland to Chicago on 13 September 2026: 2908 km of route against 2823 km in a straight line, 30 services a day, 5 operators a cheapest fare of €272.72, and 7h 16m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.
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