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Did you mean flights from Chicago to Portland, Maine?

Flights from Portland, Maine to Chicago, United States

Portland, Maine to Chicago Last modified: Apr 27, 2017 2:42 -04:00Prices shown were found by travelers like you over the past 30 days

We've scanned 17,351,303,455 round trip itineraries and found the cheapest flights to Chicago. American & JetBlue frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

American
PWMCHI
Thu 5/11
1 stop
CHIPWM
Sun 5/14
1 stop
$290
JetBlue
PWMCHI
Thu 8/24
1 stop
CHIPWM
Wed 8/30
1 stop
$354
United
PWMCHI
Wed 6/14
2 stops
CHIPWM
Sat 6/17
2 stops
$442

How Much is a Flight from Portland, Maine to Chicago? Prices shown were found by travelers like you over the past 30 days

We have collected flight cost data from across the web for travel from Portland, Maine to Chicago, and have found the average flight price for this trip to be $423.

Where To Buy Cheap Flights from Portland, Maine to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Portland, Maine to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Portland, Maine to Chicago? Prices shown were found by travelers like you over the past 30 days

The chart below shows up-to-date information regarding how far in advance to book your flight from Portland, Maine to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $0 $415
7-14 days $715 $290
14-21 days $715 $290
21-30 days $635 $356
30-60 days $635 $343
60-90 days $655 $374
90+ days $635 $311

Cheapest Day To Fly from Portland, Maine to Chicago Prices shown were found by travelers like you over the past 30 days

We've examined 17,367,816,148 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Portland, Maine to Chicago is Thursday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$511$393$340$290$382$343$696

Compare Flight Prices from Portland, Maine to Chicago by Month Prices shown were found by travelers like you over the past 30 days

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Portland, Maine to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Portland, Maine Chicago American 5/11/17 5/14/17 1 $290
June Portland, Maine Chicago American 6/3/17 6/5/17 1 $343
July Portland, Maine Chicago American 7/27/17 8/1/17 1 $373
August Portland, Maine Chicago JetBlue 8/24/17 8/30/17 1 $354
September Portland, Maine Chicago JetBlue 9/13/17 9/16/17 1 $311
October Portland, Maine Chicago JetBlue 10/20/17 10/22/17 1 $365
November Portland, Maine Chicago American 11/29/17 12/4/17 2 $346
February Portland, Maine Chicago American 2/1/18 2/8/18 2 $353

Cheap Last Minute Flights from Portland, Maine to Chicago Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Portland, Maine to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
7 8 9 10 11 12 13
$290
14 15 16 17 18 19 20
$290 $356
21 22 23 24 25 26 27
$356 $485
28 29 30 31 1 2 3
$485 $343
4 5 6 7 8 9 10
$343

Connecting Flights vs Direct Flights from Portland, Maine to Chicago Prices shown were found by travelers like you over the past 30 days

Flights between some cities may be significantly cheaper if you choose 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, Maine to Chicago is $347.

The average price for direct flights from Portland, Maine to Chicago is $637.

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

Weekly Direct Flights from Portland, Maine to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 3 3 3 4 4 06:20 16:43

One Way Flights vs Round Trip Flights from Portland, Maine to Chicago Prices shown were found by travelers like you over the past 30 days

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, Maine 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, Maine to Chicago is not available.

The average price for round trip flights from Portland, Maine to Chicago is $341.

Portland, Maine to Chicago Flight Questions

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

Question: How long is the flight from Portland, Maine to Chicago?
Answer: The average Portland, Maine to Chicago flight time is 2 hours and 52 minutes.
Question: How far is Chicago from Portland, Maine?
Answer: The distance from Portland, Maine to Chicago is 897 miles (1,443 kilometers).
Question: How common are direct flights from Portland, Maine to Chicago?
Answer: There are 21 direct flights from Portland, Maine to Chicago.
Question: What are the most popular Portland, Maine airlines for direct flights from Portland, Maine to Chicago?
Answer: United Airlines provides 100% of the non-stop flights between Portland, Maine and Chicago.
Question: What are the most popular connecting cities when flying from Portland, Maine to Chicago?
Answer: Newark, NJ

Airlines in Portland, Maine flying to Chicago Last modified: Apr 27, 2017 2:42 -04:00Number of routes searched: 181Number of itineraries searched: 88,845

Wondering which airlines fly out of Portland, Maine to Chicago? We've gathered the average price of Portland, Maine airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Portland, Maine to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
United -
American BNA
American CLT
American DCA
American IND
JetBlue JFK
Major Airlines ATL
Major Airlines DTW
United BUF
United EWR
United IAD
United ORF

Portland, Maine to Chicago Airports

These are the major commercial airports we're currently monitoring in Portland, Maine and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from Portland - PWM Last modified: Apr 27, 2017 2:42 -04:00Prices shown were found by travelers like you over the past 30 days

Cheap International Flights to Chicago - CHI Last modified: Apr 27, 2017 2:42 -04:00Prices shown were found by travelers like you over the past 30 days

Cheap Flights from Portland, Maine to Chicago