HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$55+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Portland with Cheapflights

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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$159
(Mytrip)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

June

Average price

$346

Good round-trip deal

$279 or less

Good one-way deal

$258 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Portland
Search Deals
One-way flight from Chicago (CHI) to Portland
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Portland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Portland.
Search Deals

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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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 3/110:20 amORD - PWM
1 stop21h 58mFrontier
Mon 3/38:35 pmPWM - ORD
1 stop17h 45mFrontier
Deal found 1/21$159
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 5/316:20 amORD - PWM
1 stop6h 00mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 1/20$185
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 7/56:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Wed 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Deal found 1/20$209
This KAYAK deal was found by Cheapflights users on 1/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/177:05 amORD - PWM
1 stop6h 17mDelta
Thu 2/206:00 amPWM - ORD
1 stop5h 49mDelta
Deal found 1/21$214
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 2/187:35 amMDW - PWM
1 stop7h 10mSouthwest
Thu 2/204:20 pmPWM - MDW
1 stop6h 40mSouthwest
Deal found 1/20$239
This Delta deal was found by Cheapflights users on 1/20. 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.
Sat 8/231:00 pmMDW - PWM
2 stops9h 45mDelta
Sat 8/3012:30 pmPWM - MDW
1 stop6h 33mDelta
Deal found 1/20$244
This United Airlines deal was found by Cheapflights users on 1/20. 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 10/316:00 pmORD - PWM
Nonstop2h 27mUnited Airlines
Sun 11/25:00 amPWM - ORD
1 stop5h 47mUnited Airlines
Deal found 1/20$252
This CheapOair deal was found by Cheapflights users on 1/20. 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 1/315:30 amMDW - PWM
1 stop12h 18mFrontier
Sun 2/27:06 pmPWM - MDW
1 stop16h 22mFrontier
Deal found 1/20$280
This Mytrip deal was found by Cheapflights users on 1/20. 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 3/15:15 amORD - PWM
2 stops13h 12mMultiple Airlines
Mon 3/36:18 pmPWM - ORD
2 stops28h 45mMultiple Airlines
Deal found 1/20$297
This Southwest deal was found by Cheapflights users on 1/21. 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.
Fri 2/287:00 amORD - PWM
2 stops8h 35mSouthwest
Tue 3/45:35 amPWM - ORD
1 stop9h 25mSouthwest
Deal found 1/21$309
This Sun Country Air deal was found by Cheapflights users on 1/21. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/248:10 pmORD - PWM
1 stop14h 25mSun Country Air
Thu 7/3112:32 pmPWM - ORD
1 stop7h 39mSun Country Air
Deal found 1/21$330
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Thu 6/198:50 amMDW - PWM
2 stops25h 23mMultiple Airlines
Sun 6/2212:32 pmPWM - MDW
2 stops22h 12mMultiple Airlines
Deal found 1/20$553

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

10:20 am-9:18 am

1 stop21h 58m

Portland

Mon 3/3

8:35 pm-1:20 pm

1 stop17h 45m

$159

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

6:20 am-1:20 pm

1 stop6h 00m

Portland

Sat 6/7

2:15 pm-10:20 pm

1 stop9h 05m

$185

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 7/5

6:20 pm-9:50 pm

Nonstop2h 30m

Portland

Wed 7/9

7:19 am-9:10 am

Nonstop2h 51m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 3/5

7:00 am-12:30 pm

1 stop4h 30m

Portland

Tue 3/11

6:00 am-1:05 pm

1 stop8h 05m

$217

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 4/3

6:00 am-11:28 am

1 stop4h 28m

Portland

Sun 4/6

7:00 am-12:41 pm

1 stop6h 41m

$223

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 2/18

7:35 am-3:45 pm

1 stop7h 10m

Portland

Thu 2/20

4:20 pm-10:00 pm

1 stop6h 40m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 1/31

5:30 am-6:48 pm

1 stop12h 18m

Portland

Sun 2/2

7:06 pm-10:28 am

1 stop16h 22m

$280

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 2/19

9:33 am-4:03 pm

1 stop5h 30m

Portland

Thu 2/20

6:00 am-1:05 pm

2 stops8h 05m

$283

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 3/5

4:40 pm-11:15 pm

1 stop5h 35m

Portland

Tue 3/11

4:03 pm-6:10 pm

Nonstop3h 07m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

5:15 am-7:27 pm

2 stops13h 12m

Portland

Mon 3/3

6:18 pm-10:03 pm

2 stops28h 45m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 24 results
1
2
3

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 January.
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 January 17, 2025.

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 January 21, 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 46% 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 January 21, 2025.

The most flights from CHI to PWM are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, 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 January 21, 2025.
Read reviews from past customers who have flown Delta, Frontier 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
8.1
Very good
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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
4,662 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Crew

8.7

Overall

8.1

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 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?

    Frontier, at $159, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include United Airlines and Delta. Frontier is 56% 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 $55 on Frontier. Other airlines that offer cheap prices include JetBlue from $87 and Delta from $109 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 Republic Airways (86%), United Airlines (85%) or Air New Zealand (85%) 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 $314, our data indicates the cheapest price to be $218. The most popular route (Chicago O'Hare Intl - Portland), is priced around $177.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Midway to Boston flights
St. Louis to Boston flights
O'Hare Intl to Portland flights
O'Hare Intl to Bangor flights
Midway to Portland flights
Moline to Boston flights
Midway to Bangor flights
St. Louis to Portland flights
St. Louis to Bangor flights
Peoria to Boston flights
O'Hare Intl to Augusta flights
Bloomington to Boston flights
O'Hare Intl to Bar Harbor flights
Moline to Portland flights
Peoria to Portland flights
O'Hare Intl to Rockland flights
Moline to Bangor flights
Evansville to Boston flights
Champaign to Portland flights
Springfield to Portland flights
Champaign to Boston flights
Bloomington to Portland flights
Springfield to Boston flights
Decatur to Boston flights
St. Louis to Presque Isle flights
Bloomington to Bangor flights
Champaign to Bangor flights
Peoria to Bangor flights
Dubuque to Boston flights
Dubuque to Portland flights
Evansville to Portland flights
Evansville to Bangor flights

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$182Average$340FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$333FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$330FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$221Average$406FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.