Good to know - Cheap tickets Portland — Chicago
| Cheapest flight found | $92 |
|---|---|
| Minimal flight time | 2h 21m |
| Flight distance | 1425 km |
| Most popular airline | American Eagle |
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 |
|---|---|---|
| October 2025 | ||
| September 2025 | ||
| July 2025 | ||
| June 2025 | ||
| December 2024 |
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 | |
|---|---|---|---|---|---|---|---|
| 06:14 | 08:08 | mon, tue, wed, thu, fri, sun | AA4391 | American Eagle | 2h 54m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:14 | 08:05 | tue, wed, thu, fri, sat | UA1304 | United Express | 2h 51m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:19 | 08:13 | sat | AA4391 | American Eagle | 2h 54m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:20 | 08:14 | sat | AA4391 | American Eagle | 2h 54m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:29 | 08:23 | fri | AA4391 | American Eagle | 2h 54m | Portland International Jetport — O'Hare International Airport | Select dates |
| 07:40 | 09:15 | sun | WN2794 | Southwest Airlines | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 09:45 | 11:55 | mon, tue, thu, sat | UA3635 | United Express | 3h 10m | Portland International Jetport — O'Hare International Airport | Select dates |
| 12:11 | 14:04 | daily | AA4741 | American Eagle | 2h 53m | Portland International Jetport — O'Hare International Airport | Select dates |
| 14:40 | 16:15 | mon, thu, fri | WN3796 | Southwest Airlines | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 15:28 | 17:24 | daily | AA4967 | American Eagle | 2h 56m | Portland International Jetport — O'Hare International Airport | Select dates |
Popular airlines flying Portland — Chicago
Flight Portland – Chicago is served by 7 airlines. 3 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Flights Portland — Chicago
The selection of cheap flights Portland — Chicago
Here you can find and purchase the cheapest flights Portland — Chicago from $92 and Portland — Chicago — Portland from $196.
The price of the flight Portland — Chicago (United States) — Portland from $196 (round-trip).
The average price of the flight Portland — Chicago (United States) — Portland $327 (round-trip).
- Departure city: Portland
- IATA code of the city of origin: PWM
- Departure airports: Portland International Jetport
- 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 (PWM — CHI)
The distance between Portland and Chicago 885 miles (or 1425 kilometres).
The time difference between Portland and Chicago is 1 h.
Minimal flight time from Portland to Chicago 2h 21m.
LowCostClub always do a comparison of airfares Portland — Chicago with several airlines (include American Eagle, United Express, Southwest 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 $196 while the cheapest one-way price that was available within the last week cost $92
Routes from nearby cities to Chicago
A flight from a neighbouring city can help you save money on plane tickets.
Most often, departures to Chicago are from Boston, this is the cheapest flight from $34. The nearest airports from Portland with a flight to Chicago are located in Albany.
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: AA4391, UA1304, WN2794, UA3635, AA4741, WN3796, AA4967, UA2466, OO6218, UA4744, UA3857, UA6945
Can we fly from Portland to Chicago?
Yes, you can fly from Portland to Chicago. Portland has an airport (Portland International Jetport) for flights. American Eagle, United Express, Southwest Airlines depart from Portland on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Avelo Airlines, Breeze Airways, Delta Connection, FedEx, Jet Linx Aviation, JetBlue, Sun Country Airlines.
How long does it take to fly from Portland to Chicago?
A direct flight lasts an average of 2h 21m, during which time the aircraft covers a distance of 1425 km.
How much do flights Portland — Chicago cost?
The price of flights Portland — Chicago starts from $92.
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 Jetport. 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: AA4391, UA1304, AA4391, AA4391, AA4391, WN2794, UA3635, AA4741, WN3796, AA4967, WN2794, WN2794, UA2466, UA2466, UA2466, UA2466, UA2466, UA2466, UA2466, UA2466, OO6218, UA4744, UA4744, UA3857, UA6945
What month is the cheapest to fly from Portland to Chicago?
High season is considered to be December 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: American Eagle, United Express, Southwest Airlines.
Which airlines fly from Portland to Chicago?
All the following airlines flights Portland — Chicago: American Eagle, Avelo Airlines, Breeze Airways, Delta Connection, FedEx, Jet Linx Aviation, JetBlue, Southwest Airlines, Sun Country Airlines, United Express.