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$53+ Cheap flights from Chicago (CHI) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Chicago to Portland are usually found in June or August, booked 89 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Delta)

One-way from

$53
(Mytrip)

Popular in

April

Cheapest in

June

Average price

$481
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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High demand for flights, 13% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2024.

This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:57 pmORD - PWM
1 stop5h 13mDelta
Wed 1/15:05 amPWM - ORD
1 stop5h 16mDelta
Deal found 12/17$317
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/182:55 pmORD - PWM
1 stop6h 51mAmerican Airlines
Wed 12/256:00 amPWM - ORD
1 stop7h 15mAmerican Airlines
Deal found 12/17$358
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:45 amORD - PWM
1 stop5h 50mSouthwest
Wed 1/16:00 amPWM - ORD
2 stops13h 10mSouthwest
Deal found 12/17$373
This CheapOair deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:45 amORD - PWM
1 stop28h 27mFrontier
Mon 12/3011:23 amPWM - ORD
1 stop26h 23mFrontier
Deal found 12/17$378
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:51 amORD - PWM
1 stop6h 33mUnited Airlines
Wed 1/17:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 12/17$394
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/266:25 pmMDW - PWM
1 stop3h 57mDelta
Sat 1/45:05 amPWM - MDW
1 stop4h 45mDelta
Deal found 12/17$428
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:55 amMDW - PWM
1 stop4h 35mSouthwest
Wed 1/16:00 amPWM - MDW
2 stops9h 10mSouthwest
Deal found 12/17$443
This Gotogate deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/236:49 pmMDW - PWM
1 stop23h 12mFrontier
Sun 12/297:51 pmPWM - MDW
1 stop14h 40mFrontier
Deal found 12/16$559
This Mytrip deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/288:03 pmORD - PWM
3 stops19h 32mMultiple Airlines
Mon 12/305:56 pmPWM - ORD
2 stops18h 08mMultiple Airlines
Deal found 12/17$842

Find flights from Chicago to Portland within your budget

Customize your flight search to find flights from Chicago to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 2/13

10:30 am-4:03 pm

1 stop4h 33m

Portland

Fri 2/14

5:27 am-9:55 am

1 stop5h 28m

$303

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 1/20

7:35 am-12:50 pm

1 stop4h 15m

Portland

Sun 1/26

1:25 pm-8:30 pm

2 stops8h 05m

$303

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2/7

7:30 am-10:40 pm

2 stops14h 10m

Portland

Sun 2/9

5:35 am-4:45 pm

2 stops12h 10m

$308

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 1/3

6:10 pm-9:42 pm

Nonstop2h 32m

Portland

Mon 1/6

5:20 am-11:58 am

1 stop7h 38m

$309

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 1/31

2:08 pm-11:10 pm

2 stops8h 02m

Portland

Fri 2/7

6:00 am-5:43 pm

2 stops12h 43m

$313

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 1/24

12:37 pm-11:20 am

3 stops21h 43m

Portland

Sun 1/26

5:23 pm-9:39 am

1 stop17h 16m

$340

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/14

6:20 pm-9:44 pm

Nonstop2h 24m

Portland

Sun 6/22

4:49 pm-8:56 pm

1 stop5h 07m

$348

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 12/30

6:49 pm-7:01 pm

1 stop23h 12m

Portland

Thu 1/2

7:49 pm-9:31 am

1 stop14h 42m

$709

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 2/10

11:33 am-8:12 pm

1 stop7h 39m

$53

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 2/26

7:25 am-5:38 pm

1 stop9h 13m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Portland

Get recent, data-driven insights about flights from Chicago to Portland including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on December 13, 2024.

The best time to book flights from Chicago to Portland, Maine is 89 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $296). Flying from Chicago to Portland, Maine in April is currently the most expensive (average of $498). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to PWM?

Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2024.

One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 35% on airfare.

What is the cheapest day to fly from Chicago to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 18, 2024.
Read reviews from past customers who have flown United Airlines, Delta and Frontier from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago?

    Most people fly into Portland (PWM) if they book a flight to Portland from Chicago. On average, Portland has 2 inbound flights from Chicago per day from 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • What are the cheapest airlines flying from Chicago to Portland, Maine round-trip?

    Delta, at $303, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Southwest and United Airlines. Delta is 18% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Portland, Maine one-way?

    One-way options have recently been found by users for as low as $53 on Frontier. Other airlines that offer cheap prices include American Airlines from $84 and JetBlue from $87 one-way.

  • What are the most reliable airlines from Chicago to Portland, Maine?

    No one likes to see their flight delayed. When booking a flight from Chicago to Portland, Maine consider choosing United Airlines (94%), SkyWest Airlines (93%) or Republic Airways (92%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Portland, Maine?

    Looking for the cheapest flight from Chicago to Portland, Maine? While on average our users pay $318, our data indicates the cheapest price to be $138. The most popular route (Chicago O'Hare Intl - Portland), is priced around $214.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $296). Flying from Chicago to Portland, Maine in April is currently the most expensive (average of $498). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Portland

Discover the top 4 airlines that operate flights from Chicago to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$184Average$343FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$316FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$408FlexibilityNo cancel feeOn-time69%
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