Good to know - Cheap tickets Chicago — Portland
| Cheapest flight found | $60 |
|---|---|
| Minimal flight time | 3h 52m |
| Flight distance | 2817 km |
| Most popular airline | UPS |
Airfare Chicago – Portland by month
Here you can find out in what months how much a ticket Chicago – Portland costs to buy cheap plane tickets.
| Month | One-way | Round-trip |
|---|---|---|
| November 2026 | ||
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| 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 Chicago — Portland
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 02:36 | 04:28 | tue, wed, thu, fri | 5X970 | UPS | 3h 52m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 08:10 | 10:45 | mon, thu | WN2029 | Southwest Airlines | 4h 35m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 08:35 | 11:15 | sat | WN2406 | Southwest Airlines | 4h 40m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 09:10 | 11:57 | mon, tue, wed, thu, fri, sun | UA1994 | United Express | 4h 47m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:10 | 12:00 | sat | UA1994 | United Express | 4h 50m | O'Hare International Airport — Portland International Airport | Select dates |
| 10:20 | 13:00 | sat | AS9341 | Amazon Air | 4h 40m | O'Hare International Airport — Portland International Airport | Select dates |
| 11:20 | 13:53 | tue, wed | AA442 | American Airlines | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:06 | 16:48 | mon, tue, thu, fri, sun | AS325 | Amazon Air | 4h 42m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:06 | 16:48 | fri | AS325 | AlphaSky | 4h 42m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:07 | 16:04 | mon, tue, wed | 5X2986 | UPS | 3h 57m | Chicago Rockford International Airport — Portland International Airport | Select dates |
Popular airlines flying Chicago — Portland
Flight Chicago – Portland is served by 19 airlines. 6 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Sales of tickets from Chicago to Portland in the last 48 hours
Dynamics airfare Chicago — Portland 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 Chicago — Portland
The graph shows that booking flights Chicago — Portland is best planned for December and flights Chicago — Portland — Chicago in the month of May.
Flights Chicago — Portland
The selection of cheap flights Chicago — Portland
Here you can find and purchase the cheapest flights Chicago — Portland from $60 and Chicago — Portland — Chicago from $57.
The price of the flight Chicago — Portland (United States) — Chicago from $57 (round-trip).
The average price of the flight Chicago — Portland (United States) — Chicago $374 (round-trip).
- Departure city: Chicago
- IATA code of the city of origin: CHI
- Departure 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
- Departure country: United States
- Destination city: Portland
- IATA code of the destination city: PDX
- Destination airports: Portland International Airport
- Destination country: United States
Low cost flights Chicago — Portland (CHI — PDX)
The distance between Chicago and Portland 1750 miles (or 2817 kilometres).
The time difference between Chicago and Portland is 2 h.
Minimal flight time from Chicago to Portland 3h 52m.
LowCostClub always do a comparison of airfares Chicago — Portland with several airlines (include UPS, Southwest Airlines, United Express). They will always give you all available options so you can find the cheapest flight to Portland. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — Portland. Last week, for instance, the cheapest round-trip prices stood at $57 while the cheapest one-way price that was available within the last week cost $60
Routes from nearby cities to Portland
A flight from a neighbouring city can help you save money on plane tickets.
The most frequent flight to Portland is from Bloomington. The cheapest airfare can be purchased with a flight from Grand Rapids from $158. The nearest airports from Chicago with a flight to Portland are in Madison.
Popular International routes from Chicago
Popular routes from Portland
If you are going to fly from Portland, then study the popular flights. The most popular flights from Portland:
Popular domestic routes from Chicago
FAQ about Chicago — Portland
Are there any direct flights Chicago — Portland?
Yes, they do: 5X970, WN2029, WN2406, UA1994, AS9341, AA442, AS325, 5X2986, 5X5986, WN1691, UA2850, AA819, AA3022, UA2059, UA1531, AA3028
Can we fly from Chicago to Portland?
Yes, you can fly from Chicago to Portland. Chicago has 8 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) for flights. UPS, Southwest Airlines, United Express, Amazon Air, American Airlines, AlphaSky depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, Air Transport International, Allegiant Air, British Airways (Oneworld Livery), Cathay Pacific, Delta Connection, DHL, FedEx Feeder, Frontier (Hugh the Manatee Livery), Icelandair, Jet Linx Aviation, Kalitta Charters, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Sun Country Airlines, Volaris.
How long does it take to fly from Chicago to Portland?
A direct flight lasts an average of 3h 52m, during which time the aircraft covers a distance of 2817 km.
How much do flights Chicago — Portland cost?
The price of flights Chicago — Portland starts from $60.
What days does the plane fly Chicago — Portland?
Planes fly Chicago — Portland 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Chicago and Portland?
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. In Portland — Portland International Airport.
What flights are currently flying from Chicago to Portland?
The following flights fly between Chicago and Portland: 5X970, WN2029, WN2406, UA1994, UA1994, AS9341, AA442, AS325, AS325, 5X2986, 5X2986, 5X5986, WN1691, UA2850, UA2850, AA819, AA3022, UA2059, UA1531, AA3028
What month is the cheapest to fly from Chicago to Portland?
High season is considered to be March and the cheapest month is December. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — Portland flight deals.
Which airlines direct fly from Chicago to Portland?
The following airlines have direct flights Chicago — Portland: UPS, Southwest Airlines, United Express, Amazon Air, American Airlines, AlphaSky.
Which airlines fly from Chicago to Portland?
All the following airlines flights Chicago — Portland: Air Canada, Air Transport International, Allegiant Air, AlphaSky, Amazon Air, American Airlines, British Airways (Oneworld Livery), Cathay Pacific, Delta Connection, DHL, FedEx Feeder, Frontier (Hugh the Manatee Livery), Icelandair, Jet Linx Aviation, Kalitta Charters, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Southwest Airlines, Sun Country Airlines, United Express, UPS, Volaris.