Cheap Flights from Portland to Chicago, IL, United States - PWM to CHI Last modified: Jun 30, 2016 7:38 PM
Popular flights from Portland to Chicago Last modified: Jun 30, 2016 7:38 PM
We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.
When Can I Buy the Cheapest Flight from Portland to Chicago (PWM to CHI)?
Airlines can adjust prices for plane tickets from Portland to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.
How far in advance should you book flights from Portland to Chicago
The chart below shows up-to-date information regarding how far in advance a flight from Portland to Chicago should be booked.
|Advanced Purchase||Non Stop||One Stop|
|< 7 days||$1,097||$648|
Lowest Fares Chart By Month from Portland to Chicago
The chart below shows the lowest fare by month when flying from Portland to Chicago.
|Month||Origin||Destination||Carrier||Depart Date||Return Date||Stops||Price|
Cheapest Weekend Non-Stop Flights for the Next 30 Days from Portland to Chicago
If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Portland to Chicago.
Next 30 Days
Non-Stop vs Connecting Flights from Portland to Chicago (PWM to CHI)
Your Portland to Chicago flight can be significantly cheaper by choosing a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Portland to Chicago is $314.
The average price for non-stop flights from Portland to Chicago is $613.
The chart below shows up to date information regarding non-stop flights from Portland to Chicago.
|Carrier||Mon||Tue||Wed||Thu||Fri||Sat||Sun||Earliest Flight||Latest Flight|
Round Trip vs One Way Flights from Portland to Chicago (PWM to CHI)
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Portland to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.
The average price for one way flights from Portland to Chicago is $176.
The average price for round trip flights from Portland to Chicago is $314.
Portland to Chicago Flight Questions
Below are some common questions that asked about this flight route:
Airports for Your Route
These pages contain information about the major airports in Portland and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.
Farecompare Research Tools
Cheap Domestic Flights to Chicago - CHI
|Boston to Chicago||American, Alaska, JetBlue, Spirit, United||$81|
|Hartford to Chicago||American, United||$339|
|Providence to Chicago||American, United||$247|
|Albany to Chicago||American, United||$339|
|Burlington to Chicago||American, United||$285|
|Manchester to Chicago||American, United||$144|
|Bangor to Chicago||American, United||$284|
|Boston to Atlanta||American, Spirit, United||$127|
|Boston to New York||American, JetBlue||$103|
|Boston to Milwaukee||American, United||$164|
|Boston to Dallas - Ft Worth||American, Alaska, JetBlue, Spirit, United||$98|
|Boston to Detroit||American, JetBlue, Spirit, United||$127|
|Boston to Indianapolis||American, United||$178|
|Boston to Minneapolis - St Paul||American, Alaska, Spirit, Sun Country, United||$191|
|Hartford to Milwaukee||American, United||$256|
|Boston to South Bend||United||$374|
|Boston to Grand Rapids||American, United||$210|
|Hartford to Atlanta||American, United||$158|
|Boston to Washington||American, JetBlue, United||$108|
|Boston to St Louis||American, Alaska, United||$320|
|Boston to Madison||American, Alaska, United||$326|
|Albany to Milwaukee||American, United||$264|
|Providence to Milwaukee||American, United||$224|
|Manchester to Milwaukee||American, United||$224|
|Boston to Los Angeles||American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America||$261|
|Boston to Baltimore||American, JetBlue, Spirit, United||$81|
|Boston to Columbus||American, United||$160|
Cheap International Flights to Chicago - CHI
|Boston to Toronto||Cape Air, American, Air Canada, Alaska, JetBlue, Porter, United, WestJet||$217|
|Boston to London||American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, Norwegian Air, Condor, Aer Lingus, Eurowings, Iberia, Meridiana, KLM, Lufthansa, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Corsair, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight||$493|