Flights from Portland, Maine to Chicago, United States

Did you mean flights from Chicago to Portland, Maine?

Portland, Maine to Chicago Last modified: Jan 22, 2024 8:30 -05:00

We've scanned 115,678,683 round trip itineraries and found the cheapest flights to Chicago. Frontier & Multiple Airlines frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Frontier
PWMCHI
Sat 2/10
1 stop
CHIPWM
Sat 2/17
1 stop
$179
Multiple Airlines
PWMCHI
Thu 1/25
nonstop
CHIPWM
Mon 1/29
nonstop
$180
American
PWMCHI
Thu 2/22
1 stop
CHIPWM
Tue 2/27
1 stop
$205
Major Airlines
PWMCHI
Sat 2/10
1 stop
CHIPWM
Tue 2/13
1 stop
$208
United
PWMCHI
Sat 3/23
nonstop
CHIPWM
Sat 3/30
nonstop
$279

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?

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 $461 $229
7-14 days $317 $188
14-21 days $272 $198
21-30 days $253 $179
30-60 days $253 $178
60-90 days $334 $196
90+ days $339 $208

Compare Flight Prices from Portland, Maine to Chicago by Month

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
January Portland, Maine Chicago Frontier 1/31/24 2/6/24 1 $179
February Portland, Maine Chicago Frontier 2/27/24 3/5/24 1 $178
March Portland, Maine Chicago Frontier 3/2/24 3/5/24 1 $179
April Portland, Maine Chicago American 4/5/24 4/8/24 1 $206
May Portland, Maine Chicago Major Airlines 5/1/24 5/3/24 2 $217
June Portland, Maine Chicago United 6/5/24 6/7/24 0 $400
July Portland, Maine Chicago Sun Country 7/26/24 7/28/24 1 $298
August Portland, Maine Chicago American 8/18/24 8/24/24 0 $461

Cheap Last Minute Flights from Portland, Maine to Chicago

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
$266
14 15 16 17 18 19 20
$266 $188
21 22 23 24 25 26 27
$188 $202
28 29 30 31 1 2 3
$202 $188
4 5 6 7 8 9 10
$188 $202
11 12 13 14 15 16 17
$202

Connecting Flights vs Direct Flights from Portland, Maine to Chicago

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 $312.

The average price for direct flights from Portland, Maine to Chicago is $402.

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
American 2 2 2 2 2 2 2 02:05 07:45
United 3 3 3 3 3 2 3 02:20 11:51

One Way Flights vs Round Trip Flights from Portland, Maine to Chicago

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 $130.

The average price for round trip flights from Portland, Maine to Chicago is $324.

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 49 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 34 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 58% of the non-stop flights between Portland, Maine and Chicago.

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: Jan 22, 2024 8:30 -05:00

Cheap International Flights to Chicago - CHI Last modified: Jan 22, 2024 8:30 -05:00

Cheap Flights from Portland, Maine to Chicago