Flights from Chicago to Portland, United States

Did you mean flights from Portland, Maine to Chicago?

Chicago to Portland, Maine Last modified: Mar 26, 2024 19:37 -04:00

We've scanned 117,220,093 round trip itineraries and found the cheapest flights to Portland, Maine. Frontier & Major Airlines frequently offer the best deals to Portland, Maine flights, or select your preferred carrier below to see the cheapest days to fly.

Frontier
CHIPWM
Tue 6/11
nonstop
PWMCHI
Tue 6/18
nonstop
Major Airlines
CHIPWM
Tue 7/9
1 stop
PWMCHI
Wed 7/10
1 stop
$228
American
CHIPWM
Wed 6/5
1 stop
PWMCHI
Sat 6/8
1 stop
$238
United
CHIPWM
Tue 7/16
1 stop
PWMCHI
Thu 7/18
1 stop
$356
Sun Country
CHIPWM
Sun 6/16
1 stop
PWMCHI
Sun 6/23
1 stop
$462
Multiple Airlines
CHIPWM
Mon 4/1
1 stop
PWMCHI
Fri 4/5
1 stop
$567

How Much is a Flight from Chicago to Portland, Maine?

We have collected flight cost data from across the web for travel from Chicago to Portland, Maine, and have found the average flight price for this trip to be $200.

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

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 Chicago to Portland, Maine 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 Chicago to Portland, Maine?

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

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $317 $247
7-14 days $298 $218
14-21 days $307 $202
21-30 days $262 $196
30-60 days $288 $196
60-90 days $358 $196
90+ days $295 $206

Cheapest Day To Fly from Chicago to Portland, Maine

We've examined 234,440,186 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Portland, Maine is Monday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$196$196$202$202$200 $202

Cheap Last Minute Flights from Chicago to Portland, Maine

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Portland, Maine. 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 $228
21 22 23 24 25 26 27
$228 $202
28 29 30 31 1 2 3
$202 $202
4 5 6 7 8 9 10
$202 $202
11 12 13 14 15 16 17
$202

Connecting Flights vs Direct Flights from Chicago to Portland, Maine

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 Chicago to Portland, Maine is not available.

The average price for direct flights from Chicago to Portland, Maine is not available.

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

Weekly Direct Flights from Chicago to Portland, Maine - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 2 2 2 2 2 2 2 03:45 13:29
United 3 3 3 3 3 2 3 04:10 13:00

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

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, Maine. 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. Find Flights

Chicago to Portland, Maine Flight Questions

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

Question: How long is the flight from Chicago to Portland, Maine?
Answer: The average Chicago to Portland, Maine flight time is 2 hours and 27 minutes.
Question: How far is Portland, Maine from Chicago?
Answer: The distance from Chicago to Portland, Maine is 897 miles (1,443 kilometers).
Question: How common are direct flights from Chicago to Portland, Maine?
Answer: There are 34 direct flights from Chicago to Portland, Maine.
Question: What are the most popular Chicago airlines for direct flights from Chicago to Portland, Maine?
Answer: United Airlines provides 58% of the non-stop flights between Chicago and Portland, Maine.

Chicago to Portland, Maine Airports

These are the major commercial airports we're currently monitoring in Chicago and Portland, Maine. 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 Flights from Chicago to Portland, Maine