Good to know - Cheap tickets Portland — Chicago
| Cheapest flight found | $73 |
|---|---|
| Minimal flight time | 3h 11m |
| Flight distance | 2817 km |
| Most popular airline | Southwest Airlines |
Airfare Portland – Chicago by month
Here you can find out in what months how much a ticket Portland – Chicago costs to buy cheap plane tickets.
| Month | One-way | Round-trip |
|---|---|---|
| January 2026 | ||
| December 2025 | ||
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Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.
Schedule of direct flights Portland — Chicago
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:00 | 10:55 | thu | WN3617 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 12:00 | tue, wed | WN2678 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 11:55 | tue, wed, sat | WN3617 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 12:05 | sun | WN2678 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:10 | 12:10 | thu, fri | WN2678 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:10 | 12:05 | sun | WN3946 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 12:10 | tue | WN4016 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 11:34 | tue, wed, thu | 5X5975 | UPS | 3h 14m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:31 | tue, wed, thu | 5X5975 | UPS | 3h 11m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 07:00 | 13:04 | tue, wed, thu, fri, sat | AS324 | Alaska Airlines | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
Popular airlines flying Portland — Chicago
Flight Portland – Chicago is served by 22 airlines. 5 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Dynamics airfare Portland — Chicago by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Portland — Chicago
The graph shows that booking flights Portland — Chicago is best planned for October and flights Portland — Chicago — Portland in the month of August.
Flights Portland — Chicago
The selection of cheap flights Portland — Chicago
Here you can find and purchase the cheapest flights Portland — Chicago from $73 and Portland — Chicago — Portland from $34.
The price of the flight Portland — Chicago (United States) — Portland from $34 (round-trip).
The average price of the flight Portland — Chicago (United States) — Portland $386 (round-trip).
- Departure city: Portland
- IATA code of the city of origin: PDX
- Departure airports: Portland International Airport
- Departure country: United States
- Destination city: Chicago
- IATA code of the destination city: CHI
- Destination airports: Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport
- Destination country: United States
Low cost flights Portland — Chicago (PDX — CHI)
The distance between Portland and Chicago 1750 miles (or 2817 kilometres).
The time difference between Portland and Chicago is 2 h.
Minimal flight time from Portland to Chicago 3h 11m.
LowCostClub always do a comparison of airfares Portland — Chicago with several airlines (include Southwest Airlines, UPS, Alaska Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Portland — Chicago. Last week, for instance, the cheapest round-trip prices stood at $34 while the cheapest one-way price that was available within the last week cost $73
Routes from nearby cities to Chicago
A flight from a neighbouring city can help you save money on plane tickets.
The most frequent flight to Chicago is from Pasco. The cheapest airfare can be purchased with a flight from Seattle from $48. The nearest airports from Portland with a flight to Chicago are in Walla Walla.
Popular International routes from Portland
Popular routes from Chicago
If you are going to fly from Chicago, then study the popular flights. The most popular flights from Chicago:
Popular domestic routes from Portland
FAQ about Portland — Chicago
Are there any direct flights Portland — Chicago?
Yes, they do: WN3617, WN2678, WN3946, WN4016, 5X5975, AS324, UA2635, UA2145, UA2074, AA987, UA534, AA563, AA2515, WN298, UA1850, WN1603, AS376, UA3909, AA2977, AA565, AA2985, UA1490
Can we fly from Portland to Chicago?
Yes, you can fly from Portland to Chicago. Portland has an airport (Portland International Airport) for flights. Southwest Airlines, UPS, Alaska Airlines, United Express, American Eagle depart from Portland on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Air Canada, Air Transport International, Allegiant Air, AlphaSky, British Airways, Cathay Pacific, Delta Connection, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), Icelandair, Jet Linx Aviation, Kalitta Charters, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Spirit Airlines, Sun Country Airlines, Volaris.
How long does it take to fly from Portland to Chicago?
A direct flight lasts an average of 3h 11m, during which time the aircraft covers a distance of 2817 km.
How much do flights Portland — Chicago cost?
The price of flights Portland — Chicago starts from $73.
What days does the plane fly Portland — Chicago?
Planes fly Portland — Chicago 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Portland and Chicago?
In Portland — Portland International Airport. In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport.
What flights are currently flying from Portland to Chicago?
The following flights fly between Portland and Chicago: WN3617, WN2678, WN3617, WN2678, WN2678, WN3946, WN4016, 5X5975, 5X5975, AS324, UA2635, UA2145, AS324, UA2074, AA987, UA534, AA987, AA563, AA2515, AA2515, WN298, AA563, UA1850, WN1603, AS376, UA3909, AS376, AS376, AS376, AA2977, AA565, AA2985, AA565, UA1490, UA1490, UA1490, UA1490, AS376
What month is the cheapest to fly from Portland to Chicago?
High season is considered to be March and the cheapest month is October. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Portland — Chicago flight deals.
Which airlines direct fly from Portland to Chicago?
The following airlines have direct flights Portland — Chicago: Southwest Airlines, UPS, Alaska Airlines, United Express, American Eagle.
Which airlines fly from Portland to Chicago?
All the following airlines flights Portland — Chicago: ABX Air, Air Canada, Air Transport International, Alaska Airlines, Allegiant Air, AlphaSky, American Eagle, British Airways, Cathay Pacific, Delta Connection, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), Icelandair, Jet Linx Aviation, Kalitta Charters, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Express, UPS, Volaris.