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

Popular flights from Chicago to Portland

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

American Airlines
Departure Date Return Date Lowest Price
Mar 17, 2016 Mar 23, 2016 $329
Apr 7, 2016 Apr 11, 2016 $329
JetBlue Airways
Departure Date Return Date Lowest Price
May 9, 2016 May 17, 2016 $282
Jun 8, 2016 Jun 11, 2016 $282
United Airlines
Departure Date Return Date Lowest Price
Apr 7, 2016 Apr 11, 2016 $343

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 $374.

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 $925 $820
7-14 days $728 $529
14-21 days $641 $436
21-30 days $613 $506
30-60 days $575 $343
60-90 days $575 $282
90+ days $577 $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
$282 $348 $352 $329 $380 $496 $432

Lowest Fares Chart By Month from Chicago to Portland

The chart below shows the lowest fare by month when flying from Chicago to Portland.

Month Origin Destination Carrier Depart Date Return Date Stops Price
February Chicago Portland JetBlue 2/23/16 3/3/16 1 $529
March Chicago Portland American 3/17/16 3/23/16 2 $329
April Chicago Portland American 4/7/16 4/11/16 2 $329
May Chicago Portland JetBlue 5/9/16 5/17/16 1 $282
June Chicago Portland JetBlue 6/8/16 6/11/16 1 $282
July Chicago Portland JetBlue 7/23/16 7/30/16 1 $333
August Chicago Portland JetBlue 8/10/16 8/19/16 1 $282
September Chicago Portland JetBlue 9/10/16 9/17/16 1 $282

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
21 22 23 24 25 26 27
$728
28 29 1 2 3 4 5
$728 $641
6 7 8 9 10 11 12
$641
13 14 15 16 17 18 19
$696
20 21 22 23 24 25 26
$696

TIPSave $310 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 $338.

The average price for non-stop flights from Chicago to Portland is $575.

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 2 2 2 2 2 2 2 13:45 17:20

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 $180.

The average price for round trip flights from Chicago to Portland is $338.

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 19 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 14 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 DCA X X X X X X X
JetBlue JFK X X X X X X X
Delta LGA X X X X X X X
Delta MSP / DTW X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest BWI 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, JetBlue, Spirit, United $77
Chicago to Boston American, JetBlue, Spirit, United $81
Chicago to Washington American, JetBlue, Frontier, United $97
Chicago to Newark American, JetBlue, United $163
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $93
Chicago to Manchester American, United $173
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $113
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $77
Chicago to Providence American, United $178
Chicago to Atlanta American, Alaska, Spirit, United $77
Chicago to Philadelphia American, Frontier, Spirit, United $77
Chicago to Dallas - Ft Worth American, Spirit, United $77
Chicago to Miami American, Frontier, United $102

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Toronto Air Choice One, American, Air Canada, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet $234
Chicago to Montreal American, Air Canada, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet $235

Cheap Domestic Flights to Portland - PWM

FlightsAirlineLowest Price
Milwaukee to Portland American, United $269
Indianapolis to Portland American, United $268
Madison to Portland American, United $314
Grand Rapids to Portland American, United $321
South Bend to Portland United $395
Appleton to Portland United $622
Peoria to Portland American, United $449
Moline to Portland American, United $322
Green Bay to Portland American, United $872
Kalamazoo to Portland American, United Check Dates
Ft Wayne to Portland American, United Check Dates
Bloomington - Normal to Portland American Check Dates
Lansing to Portland United $858
Indianapolis to Boston American, JetBlue, United $167
Milwaukee to Boston American, Alaska, United $202
Cheap Flights from Chicago to Portland, ME, United States, from $282 Round trip from CHI to PWM