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Cheap Flights from Chicago to Portland, ME, United States - CHI to PWM

Popular flights from Chicago to Portland

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.

American Airlines
Departure Date Return Date Lowest Price
Jun 14, 2016 Jun 22, 2016 $246
JetBlue Airways
Departure Date Return Date Lowest Price
May 18, 2016 Jun 1, 2016 $262
May 24, 2016 May 29, 2016 $262
United Airlines
Departure Date Return Date Lowest Price
May 10, 2016 May 21, 2016 $444

How Much Does it Cost to Fly from Chicago to Portland (CHI to PWM)?

We have collected flight cost data from across the web for travel from Chicago to Portland, and have found the average flight price for this trip to be $306.

When Can I Buy the Cheapest Flight from Chicago to Portland (CHI to PWM)?

Airlines can adjust prices for plane tickets from Chicago to Portland 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 Chicago to Portland

The chart below shows up-to-date information regarding how far in advance a flight from Chicago to Portland should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $935 $426
7-14 days $693 $262
14-21 days $621 $262
21-30 days $597 $282
30-60 days $597 $282
60-90 days $601 $318
90+ days $597 $282

Cheapest Day To Fly from Chicago to Portland

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Portland.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$349 $246 $262 $318 $318 $282 $366

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Chicago to Portland

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 Chicago to Portland.

Next 30 Days

SunMonTueWedThuFriSat
8 9 10 11 12 13 14
$786
15 16 17 18 19 20 21
$786
22 23 24 25 26 27 28
$621
29 30 31 1 2 3 4
$621 $601
5 6 7 8 9 10 11
$601 $601
12 13 14 15 16 17 18
$601

TIPSave $280 by flying into Boston instead of Portland from Chicago

Non-Stop vs Connecting Flights from Chicago to Portland (CHI to PWM)

Your Chicago to Portland 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 Chicago to Portland is $374.

The average price for non-stop flights from Chicago to Portland is $597.

The chart below shows up to date information regarding non-stop flights from Chicago to Portland.

Nonstop Flight Details from Chicago to Portland
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 3 3 3 3 3 07:29 19:15

Round Trip vs One Way Flights from Chicago to Portland (CHI to PWM)

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 Chicago to Portland. 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 Chicago to Portland is $167.

The average price for round trip flights from Chicago to Portland is $374.

Chicago to Portland Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is a direct flight from Chicago to Portland?
Answer: The average Chicago to Portland flight time is 2 hours and 20 minutes.
Question: How many miles are there between Chicago and Portland?
Answer: The distance from Chicago to Portland is 897 miles.
Question: How common are direct flights from Chicago to Portland?
Answer: There are 21 direct flights from Chicago to Portland.
Question: What is the most popular airline for non-stop flights from Chicago to Portland?
Answer: United Airlines provides 100% of the non-stop flights between Chicago and Portland.
Question: What are the most popular connecting cities when flying from Chicago to Portland?
Answer: Atlanta, GA

Airlines Flying from Chicago to Portland (CHI to PWM)

Below are the different airlines that fly from Chicago to Portland with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Portland.

Chicago to Portland
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American PHL X X X X X X X
JetBlue JFK X X X X X X X
Delta DTW X X X X X X X
Delta CVG / LGA X X X X X X X
United - X X X X X X X
United IAD X X X X X X X
Southwest BWI X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Portland, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to New York American, Alaska, JetBlue, Spirit, United $109
Chicago to Boston American, JetBlue, Spirit, United $89
Chicago to Washington American, Alaska, Frontier, United $88
Chicago to Newark American, Alaska, JetBlue, United $147
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $137
Chicago to Manchester American, United $228
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $107
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $167
Chicago to Providence American, United $213
Chicago to Atlanta American, Spirit, United $71
Chicago to Philadelphia American, Alaska, Frontier, Spirit, United $71
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $87
Chicago to Miami American, Alaska, Frontier, United $108

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet, Great Lakes $227
Chicago to Montreal American, Air Canada, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet, Great Lakes $266

Cheap Domestic Flights to Portland - PWM

FlightsAirlineLowest Price
Milwaukee to Portland American, United $261
Indianapolis to Portland American, United $220
Madison to Portland American, United $346
Grand Rapids to Portland American, United $298
South Bend to Portland United $499
Appleton to Portland United Check Dates
Peoria to Portland American, United $669
Moline to Portland American, United $628
Green Bay to Portland American, United $546
Kalamazoo to Portland American, United $472
Ft Wayne to Portland American, United $422
Bloomington - Normal to Portland American $735
Lansing to Portland American, United $666
Indianapolis to Boston American, Alaska, JetBlue, United $203
Milwaukee to Boston American, Alaska, United $204
Cheap Flights from Chicago to Portland, ME, United States, from $246 Round trip from CHI to PWM