From
To
City
Select sites to compare prices
Enter your destination to continue
Enter your travel dates to continue
Select at least 3 sites to continue
Select your depart date
Select your return date

Find Flights

Search

Did you mean flights from Portland, Maine to Chicago?

Flights from Chicago to Portland, United States

TIPSave $329 by flying into Boston instead of Portland, Maine from Chicago

Chicago to Portland, Maine Last modified: Feb 23, 2017 1:16 -05:00Prices shown were found by travelers like you over the past 30 days

We've scanned 28,669,780,732 round trip itineraries and found the cheapest flights to Portland, Maine. American & JetBlue frequently offer the best deals to Portland, Maine flights, or select your preferred carrier below to see the cheapest days to fly.

American
CHIPWM
Tue 5/2
2 stops
PWMCHI
Tue 5/9
2 stops
$312
JetBlue
CHIPWM
Tue 5/16
1 stop
PWMCHI
Tue 5/23
1 stop
$343
United
CHIPWM
Thu 3/30
1 stop
PWMCHI
Thu 4/6
1 stop
$404

How Much is a Flight from Chicago to Portland, Maine? 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 Chicago to Portland, Maine, and have found the average flight price for this trip to be $370.

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? 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 Chicago to Portland, Maine.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $1,119 $533
7-14 days $700 $417
14-21 days $685 $413
21-30 days $660 $458
30-60 days $655 $347
60-90 days $635 $312
90+ days $635 $200

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

We've examined 28,689,091,434 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 Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$347$312$371$351$351$368$485

Compare Flight Prices from Chicago to Portland, Maine 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 Chicago to Portland, Maine flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
February Chicago Portland, Maine JetBlue 2/23/17 2/28/17 1 $533
March Chicago Portland, Maine American 3/27/17 3/29/17 2 $347
April Chicago Portland, Maine American 4/28/17 4/30/17 2 $369
May Chicago Portland, Maine American 5/2/17 5/9/17 2 $312
June Chicago Portland, Maine JetBlue 6/21/17 6/26/17 1 $363
July Chicago Portland, Maine American 7/11/17 7/18/17 2 $395
August Chicago Portland, Maine JetBlue 8/21/17 8/30/17 1 $291
September Chicago Portland, Maine American 9/12/17 9/15/17 2 $385

Cheap Last Minute Flights from Chicago to Portland, Maine 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 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
26 27 28 1 2 3 4
$419
5 6 7 8 9 10 11
$419 $423
12 13 14 15 16 17 18
$423 $458
19 20 21 22 23 24 25
$458 $680
26 27 28 29 30 31 1
$680 $552
2 3 4 5 6 7 8
$552

Connecting Flights vs Direct Flights from Chicago to Portland, Maine 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 Chicago to Portland, Maine is $389.

The average price for direct flights from Chicago to Portland, Maine is $688.

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
United 2 2 2 2 2 2 2 13:50 17:35

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

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

The average price for round trip flights from Chicago to Portland, Maine is $379.

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 22 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 14 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 100% of the non-stop flights between Chicago and Portland, Maine.
Question: What are the most popular connecting cities when flying from Chicago to Portland, Maine?
Answer: Newark, NJ

Airlines in Chicago flying to Portland, Maine Last modified: Feb 23, 2017 1:16 -05:00Number of routes searched: 171Number of itineraries searched: 72,423

Wondering which airlines fly out of Chicago to Portland, Maine? We've gathered the average price of Chicago airlines with flights to Portland, Maine. 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.

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

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 International Flights from Chicago - CHI Last modified: Feb 23, 2017 1:16 -05:00Prices shown were found by travelers like you over the past 30 days

Cheap Flights from Chicago to Portland, Maine