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Portland

$90+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Portland are usually found in February or June, booked 61 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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(American Airlines)

One-way from

$90
(United Airlines)

Popular in

December

Cheapest in

February

Average price

$425

Good round-trip deal

$297 or less

Good one-way deal

$129 or less
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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Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Portland.
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Price to beat on a one-way flight from Chicago (CHI) to Portland.
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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 April 1, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. 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 7/97:00 amORD - PWM
1 stop7h 13mAmerican Airlines
Sat 7/126:01 pmPWM - ORD
1 stop6h 56mAmerican Airlines
Deal found 3/31$229
This Southwest deal was found by Cheapflights users on 3/31. 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 6/305:05 amMDW - PWM
1 stop4h 35mSouthwest
Thu 7/31:20 pmPWM - MDW
1 stop5h 05mSouthwest
Deal found 3/31$229
This JetBlue Airways deal was found by Cheapflights users on 3/31. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:10 amORD - PWM
1 stop6h 10mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 3/31$232
This Delta deal was found by Cheapflights users on 3/31. 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.
Tue 7/13:40 pmORD - PWM
1 stop7h 48mDelta
Thu 7/36:56 pmPWM - ORD
1 stop6h 03mDelta
Deal found 3/31$233
This Delta deal was found by Cheapflights users on 3/31. 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.
Tue 7/14:24 pmMDW - PWM
1 stop7h 04mDelta
Thu 7/311:44 amPWM - MDW
1 stop7h 01mDelta
Deal found 3/31$233
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Fri 7/114:46 pmORD - PWM
1 stop5h 28mUnited Airlines
Thu 7/246:10 amPWM - ORD
Nonstop2h 55mUnited Airlines
Deal found 3/30$240
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Fri 4/119:54 amORD - PWM
1 stop22h 18mFrontier
Sun 4/1310:08 amPWM - ORD
1 stop23h 36mFrontier
Deal found 4/1$247
This CheapOair deal was found by Cheapflights users on 3/31. 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.
Fri 5/91:19 pmMDW - PWM
1 stop28h 07mFrontier
Sun 5/118:23 pmPWM - MDW
1 stop17h 01mFrontier
Deal found 3/31$260
This Southwest deal was found by Cheapflights users on 4/1. 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.
Thu 8/2111:25 amORD - PWM
2 stops10h 45mSouthwest
Sun 8/245:35 amPWM - ORD
1 stop7h 15mSouthwest
Deal found 4/1$279

Cheapflights Fare Finder

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 April 1, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/19

6:12 pm-9:35 pm

Nonstop2h 23m

Portland

Thu 4/24

6:45 pm-11:29 pm

1 stop5h 44m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 6/30

5:05 am-10:40 am

1 stop4h 35m

Portland

Thu 7/3

1:20 pm-5:25 pm

1 stop5h 05m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

6:10 am-1:20 pm

1 stop6h 10m

Portland

Sat 6/7

2:15 pm-10:20 pm

1 stop9h 05m

$232

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 7/1

4:24 pm-12:28 am

1 stop7h 04m

Portland

Thu 7/3

11:44 am-5:45 pm

1 stop7h 01m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 5/27

8:00 am-11:32 am

Nonstop2h 32m

Portland

Fri 5/30

12:08 pm-1:58 pm

Nonstop2h 50m

$234

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

4:25 pm-11:59 pm

1 stop6h 34m

Portland

Sat 6/7

6:35 am-1:04 pm

1 stop7h 29m

$243

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 4/11

9:54 am-9:12 am

1 stop22h 18m

Portland

Sun 4/13

10:08 am-8:44 am

1 stop23h 36m

$247

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 5/9

1:19 pm-6:26 pm

1 stop28h 07m

Portland

Sun 5/11

8:23 pm-12:24 pm

1 stop17h 01m

$260

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 5/8

6:00 am-3:55 pm

2 stops8h 55m

Portland

Sun 5/11

5:40 am-11:50 am

1 stop7h 10m

$298

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 5/22

4:35 pm-7:37 pm

2 stops26h 02m

Portland

Thu 5/29

12:47 pm-7:09 pm

1 stop7h 22m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 22 results
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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 April.
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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Portland

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 March 28, 2025.

The best time to book flights from Chicago to Portland, Maine is 61 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 May is currently the most expensive (average of $416). 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 April 1, 2025.

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 45% 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. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Portland, Maine

Explore weekly flight availability from Chicago to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 1, 2025.

The most flights from CHI to PWM are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

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 April 1, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,276 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 3 inbound flights from Chicago per day from 5 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?

    American Airlines, at $229, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Southwest and JetBlue. American Airlines is 35% 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 $90 on United Airlines. Other airlines that offer cheap prices include JetBlue from $92 and American Airlines from $105 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 SkyWest Airlines (77%), Air New Zealand (70%) or United Airlines (66%) 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 $285, our data indicates the cheapest price to be $89. The most popular route (Chicago O'Hare Intl - Portland), is priced around $163.

  • 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 May is currently the most expensive (average of $416). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Alternative routes for Chicago to Portland

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Top 5 airlines flying from Chicago to Portland

Discover the top 5 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$89FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$341FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
DeltaCheapest$217Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$389FlexibilityNo cancel feeOn-time69%

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