Chicago to Portland runs about 30 times a day, with the first departure around 06:02 and the last around 20:12. One passenger pays between €221.39 and €233.19, every fee included, depending on the operator and the way you travel. The fastest door to door is 7h 13m over 2,908 km, on services run by 5 operators across 1 mode.
What one seat costs
The spread between the cheapest and dearest typical fare on this corridor, across 5 operators and 1 way of making the journey. The operator sets the price on the day.
Typical fares
€221.39 to €233.19
- 132%Moves across the booking window
When it runs, leaving Chicago
No operator has filed a timetable for this direction yet, so the first and last departure below follow the pattern of the corridor. Read them as the shape of the service day rather than as times to turn up for.
- 06:02First departure
- 20:12Last departure
- 30Services per day
- 100%Run direct
Fares by date
What this journey usually costs, by departure date. It shows which days run dearer.
Typical fares
- 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
- about €232.60Mon28
- about €237.32Tue29
- about €243.81Wed30
- about €280.98Thu1
- about €262.69Fri2
- about €266.82Sat3
- about €247.35Sun4
- about €221.39Mon5
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 flight gets you into Portland. It does not get you a bed, and neither do we.
A room in Portland for the night the flight gets in
Sort by distance from Hall/Nimbus and you can see which places are ten minutes on foot and which are not.
Search Portland 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 Chicago to Portland
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €257.3890 days
- €210.1860 days
- €242.6345 days
- €197.2030 days
- €221.3921 days
- €232.6014 days
- €275.677 days
- €457.983 days
- €411.961 days
- Cheapest lead time
- Fares bottom out around 30 days ahead, at €197.20.
- How much it moves
- The gap between the cheapest and dearest lead time is 132 percent. The dearest point is €457.98, 3 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.
Book now Fares on this route are lowest around 30 days ahead. You are inside that window.
This corridor, specifically
Facts that apply to Chicago to Portland and to no other route on the site.
Clocks
2 hours behind on arrival. You land earlier than the journey suggests.
The shape of it
2,908 km
2,823 km as the crow flies, 3% further by the route services actually take. The bearing runs west.
Who lives at each end
2,664,452 → 652,503
Population at the departure city and at the arrival city, which is usually what decides how often anything runs.
How we know
Observed
Every operator on this corridor is named in a carrier record.
The route
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 2,908 km against 2,823 km in a straight line, a detour of 3 percent. Track and road geometry account for the difference.
Who runs this route
The flight gets in hours before any room is ready. Holding a bag is not what we sell.
Left luggage near Hall/Nimbus
Most of the points near Hall/Nimbus open before the first train and shut after the last one.
Check Portland 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.
Questions about Chicago to Portland
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 it take to get from Chicago to Portland?
The fastest journey from Chicago to Portland takes 7h 13m door to door, of which 4h 5m is spent moving, on the flight. Most services take around 7h 31m, because that average includes slower stopping services and journeys with a connection. Times include reaching the terminal and leaving it at the far end.
How much does it cost to travel from Chicago to Portland?
The cheapest fare from Chicago to Portland is €221.39, as of 14 September 2026. A typical fare across the next three weeks is €376.56. Both figures are the total for one passenger, including taxes, supplier fees and our service fee, so nothing is added at checkout.
What is the cheapest way to get from Chicago to Portland?
The cheapest way from Chicago to Portland is by flight, at €232.60 for one passenger on 5 October 2026. That journey takes 7h 15m 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.
When should I book Chicago to Portland?
Fares from Chicago to Portland bottom out around 30 days before departure, at €197.20. Across the whole booking window the gap between the cheapest and the dearest lead time is 132 percent, measured on 14 September 2026. Booking inside the last week has consistently cost more on this corridor.
Which day of the week is cheapest for Chicago to Portland?
Monday is the cheapest day to depart from Chicago to Portland, at €232.60. That is the median of 21 priced departure days across the next three weeks, as of 14 September 2026. Shifting a departure by one day is usually worth more than shifting the booking by one week.
Which month is cheapest for Chicago to Portland?
February is the cheapest of the next 6 months to travel from Chicago to Portland, at €180.09 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.
Who runs services from Chicago to Portland?
5 operators sell services from Chicago to Portland across 1 mode: Alaska Airlines, American Airlines, Asiana Airlines, Southwest Airlines, United 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.
Is there a direct service from Chicago to Portland?
Every service we sell from Chicago to Portland is direct, with around 30 departures a day and a fastest journey of 7h 13m door to door. No connection is needed, so there is no missed connection risk to plan around on this corridor.
Which station or terminal do services from Chicago to Portland use?
Services from Chicago to Portland by flight leave from Chicago ORD and arrive at Portland PDX. 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.
Can I change or refund a ticket from Chicago to Portland?
0 of the 5 operators we sell from Chicago to Portland 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.
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, Distances
- On this page
- Every figure above was computed for Chicago to Portland on 14 September 2026: 2908 km of route against 2823 km in a straight line, 30 services a day, 5 operators a cheapest fare of €221.39, and 7h 13m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.
The flight is the simple part. What you do once you are in Portland is somebody else's catalogue.
Day trips out of Portland and across United States
Day trips that leave Portland in the morning and cover a good part of United States by evening.
See Portland 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.
The two ends, compared
Chicago reaches 266 places in 40 countries on services we hold, over distances from 41 to 12,539 km. Portland reaches 91 places in 9 countries, from 70 to 8,451 km.
Other ways to make this journey
Leaving Chicago
- 266Places you can leave for
- 40Countries
- 77Operators
Arriving in Portland
Leaving Portland
- 91Places you can leave for
- 9Countries
- 30Operators