HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$70+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
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.

Cheapflights Tip: The best prices from Chicago to Portland are usually found in February or March, booked 58 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap 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 5, 2025.

This Delta deal was found by Cheapflights users on 12/4. 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.
Fri 12/121:20 pmORD - PWM
1 stop8h 03mDelta
Sat 1/172:35 pmPWM - ORD
1 stop7h 18mDelta
Deal found 12/4$263
This Delta deal was found by Cheapflights users on 12/3. 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 12/189:40 amORD - PWM
1 stop5h 23mDelta
Mon 12/225:45 amPWM - ORD
1 stop6h 42mDelta
Deal found 12/3$269
This Delta deal was found by Cheapflights users on 12/4. 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 12/1711:15 amORD - PWM
2 stops11h 49mDelta
Tue 1/66:17 amPWM - ORD
2 stops11h 27mDelta
Deal found 12/4$273
This Delta deal was found by Cheapflights users on 12/3. 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 12/186:45 amORD - PWM
1 stop4h 28mDelta
Sun 12/211:03 pmPWM - ORD
2 stops9h 11mDelta
Deal found 12/3$274
This Delta deal was found by Cheapflights users on 12/2. 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 12/319:41 amORD - PWM
2 stops12h 02mDelta
Mon 1/55:57 pmPWM - ORD
1 stop5h 37mDelta
Deal found 12/2$284
This United Airlines deal was found by Cheapflights users on 12/4. 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.
Thu 12/258:50 amORD - PWM
1 stop4h 50mUnited Airlines
Sat 12/279:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 12/4$289
This American Airlines deal was found by Cheapflights users on 12/4. 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 12/3111:35 amORD - PWM
1 stop4h 04mAmerican Airlines
Tue 1/65:07 pmPWM - ORD
1 stop6h 27mAmerican Airlines
Deal found 12/4$294
This Delta deal was found by Cheapflights users on 12/3. 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 12/204:00 pmORD - PWM
1 stop5h 43mDelta
Mon 12/225:45 amPWM - ORD
1 stop6h 42mDelta
Deal found 12/3$299
This Delta deal was found by Cheapflights users on 12/3. 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 12/319:41 amORD - PWM
2 stops12h 02mDelta
Tue 1/65:57 pmPWM - ORD
1 stop5h 37mDelta
Deal found 12/3$303
This Delta deal was found by Cheapflights users on 12/4. 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 12/179:34 amMDW - PWM
1 stop5h 33mDelta
Tue 1/66:17 amPWM - MDW
2 stops11h 12mDelta
Deal found 12/4$304
This Southwest deal was found by Cheapflights users on 12/3. 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 12/305:45 amMDW - PWM
1 stop4h 25mSouthwest
Tue 1/612:45 pmPWM - MDW
1 stop7h 15mSouthwest
Deal found 12/3$317
This Southwest deal was found by Cheapflights users on 12/4. 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.
Sun 12/145:10 amMDW - PWM
1 stop5h 00mSouthwest
Tue 12/163:30 pmPWM - MDW
1 stop6h 35mSouthwest
Deal found 12/4$329

Find 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 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Southwest)

One-way from

$70
(Southwest)

Popular in

November

Cheapest in

February

Average price

$420

Good round-trip deal

$284 or less

Good one-way deal

$340 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. 13% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 5, 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

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/8

6:50 am-12:10 pm

1 stop4h 20m

Portland

Tue 1/13

12:45 pm-6:35 pm

2 stops6h 50m

$194

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 1/31

7:00 am-1:45 pm

1 stop5h 45m

Portland

Sat 2/7

6:17 am-1:50 pm

1 stop8h 33m

$197

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

5:30 am-5:16 pm

2 stops10h 46m

Portland

Tue 1/13

5:57 pm-10:34 pm

1 stop5h 37m

$202

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 1/31

11:00 am-2:39 pm

Nonstop2h 39m

Portland

Sat 2/7

4:10 pm-6:18 pm

Nonstop3h 08m

$209

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 2/25

9:50 am-2:55 pm

1 stop4h 05m

Portland

Mon 3/2

1:00 pm-5:35 pm

1 stop5h 35m

$214

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/1

3:29 pm-10:43 pm

1 stop6h 14m

Portland

Tue 1/6

6:17 am-4:29 pm

2 stops11h 12m

$218

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

12:00 pm-6:50 pm

1 stop5h 50m

Portland

Tue 1/13

11:12 am-4:06 pm

1 stop5h 54m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 1/23

1:26 pm-10:27 pm

2 stops8h 01m

Portland

Mon 1/26

2:35 pm-10:22 pm

2 stops8h 47m

$230

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/1

7:00 am-12:17 pm

1 stop4h 17m

Portland

Tue 1/6

5:57 pm-10:34 pm

1 stop5h 37m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 2/25

11:48 am-3:14 pm

Nonstop2h 26m

Portland

Mon 3/2

6:00 am-11:32 am

1 stop6h 32m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 33 results
1
2
3
4

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 Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Portland, Maine flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 28, 2025.

The best time to book flights from Chicago to Portland, Maine is 58 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, September is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $91). Flying from Chicago to Portland, Maine in February is currently the most expensive (average of $138). 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 5, 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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% 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 November 29, 2025.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons 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 December 5, 2025.

The most flights from CHI to PWM are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

How often are flights from Chicago to Portland delayed?

About 15% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 127 minutes.

What is the most punctual flight time for Chicago to Portland flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Portland flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 6% of flights being delayed.

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 5, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,010 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,064 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,047 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,898 reviews
Southwest
8.0
Very good
4,251 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 5 inbound flights from Chicago per day from 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Chicago to Portland, Maine?

    There are many flights that can get you from Chicago to Portland, Maine in 2h 39m. Fly via Southwest, Delta, or United Airlines to get the fastest option. There are 897 mi between Chicago and Portland, Maine. This flight may include one or multiple stops.

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

    Delta, at $108, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Delta is 70% 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 $89 on American Airlines. Other airlines that offer cheap prices include Delta from $114 and United Airlines from $115 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 Air New Zealand (86%), Republic Airways (70%) or Emirates (69%) 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 $397, our data indicates the cheapest price to be $195. The most popular route (Chicago O'Hare Intl - Portland), is priced around $197.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $91). Flying from Chicago to Portland, Maine in February is currently the most expensive (average of $138). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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
O'Hare Intl to Portland flights
St. Louis to Boston flights
Midway to Portland flights
O'Hare Intl to Bangor flights
Moline to Boston flights
Peoria to Boston flights
St. Louis to Portland flights
St. Louis to Bangor flights
Midway to Bangor flights
Dubuque to Boston flights
Bloomington to Boston flights
Moline to Bangor flights
Peoria to Portland flights
Evansville to Boston flights
O'Hare Intl to Augusta flights
O'Hare Intl to Bar Harbor flights
Springfield to Boston flights
Peoria to Bangor flights
O'Hare Intl to Rockland flights
Evansville to Bangor flights
Bloomington to Bangor flights
Springfield to Portland flights
Bloomington to Portland flights
Moline to Portland flights
Decatur to Boston flights
Champaign to Boston flights
Dubuque to Portland flights
Evansville to Portland flights
Champaign to Bangor flights
Champaign to Portland flights
St. Louis to Presque Isle flights

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 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$222Average$377FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$233Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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.
Site
Cookie settings©2025 Cheapflights