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$96+ Cheap flights from Portland, ME (PWM) to Chicago (CHI)

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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Portland to Chicago are usually found in September or May, booked 71 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Portland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(United Airlines)

One-way from

$96
(Priceline)

Popular in

December

Cheapest in

September

Average price

$391

Good round-trip deal

$337 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Portland to Chicago (CHI)
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One-way flight from Portland to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($45 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 November 2025
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Price to beat on a round-trip flight from Portland to Chicago (CHI).
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Price to beat on a one-way flight from Portland to Chicago (CHI).
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Find flight deals from Portland to Chicago

Cheapest flights from Portland to Chicago
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Delta deal was found by Cheapflights users on 11/11. 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 12/44:53 pmPWM - ORD
1 stop4h 42mDelta
Mon 12/87:00 amORD - PWM
1 stop5h 54mDelta
Deal found 11/11$229
This Southwest deal was found by Cheapflights users on 11/11. 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 12/115:30 amPWM - MDW
1 stop5h 40mSouthwest
Sat 12/134:45 pmMDW - PWM
1 stop4h 10mSouthwest
Deal found 11/11$229
This Delta deal was found by Cheapflights users on 11/12. 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 12/124:43 pmPWM - ORD
1 stop6h 47mDelta
Mon 12/152:30 pmORD - PWM
2 stops7h 51mDelta
Deal found 11/12$234
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 11/245:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Fri 11/284:05 pmORD - PWM
1 stop5h 28mAmerican Airlines
Deal found 11/12$239
This United Airlines deal was found by Cheapflights users on 11/11. 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 11/264:40 pmPWM - ORD
Nonstop3h 01mUnited Airlines
Thu 11/2710:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 11/11$249
This Delta deal was found by Cheapflights users on 11/11. 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 12/42:34 pmPWM - MDW
2 stops10h 13mDelta
Mon 12/810:49 amMDW - PWM
2 stops11h 32mDelta
Deal found 11/11$259
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/36:00 amPWM - ORD
1 stop5h 59mAmerican Airlines
Sun 12/76:05 amORD - PWM
1 stop4h 32mAmerican Airlines
Deal found 11/11$260
This United Airlines deal was found by Cheapflights users on 11/11. 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 12/116:00 amPWM - ORD
1 stop5h 44mUnited Airlines
Sat 12/135:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 11/11$261
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 11/277:02 amPWM - ORD
1 stop8h 12mAmerican Airlines
Fri 11/284:05 pmORD - PWM
1 stop5h 28mAmerican Airlines
Deal found 11/11$269
This Southwest deal was found by Cheapflights users on 11/11. 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 12/43:30 pmPWM - MDW
1 stop6h 35mSouthwest
Mon 12/82:30 pmMDW - PWM
2 stops6h 45mSouthwest
Deal found 11/11$279
This Delta deal was found by Cheapflights users on 11/13. 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 12/114:53 pmPWM - ORD
1 stop4h 42mDelta
Sat 12/136:00 amORD - PWM
2 stops9h 00mDelta
Deal found 11/13$284
This Southwest deal was found by Cheapflights users on 11/12. 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 12/153:30 pmPWM - MDW
1 stop6h 35mSouthwest
Thu 12/185:10 amMDW - PWM
1 stop5h 00mSouthwest
Deal found 11/12$296

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Chicago 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 November 13, 2025.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.

Fly from

Portland

Fly to

Chicago

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 12/11

6:00 am-10:44 am

1 stop5h 44m

Chicago O'Hare Intl

Sat 12/13

8:45 am-2:19 pm

1 stop4h 34m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 12/12

4:43 pm-10:30 pm

1 stop6h 47m

Chicago O'Hare Intl

Mon 12/15

8:55 am-4:07 pm

1 stop6h 12m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 12/11

5:30 am-10:10 am

1 stop5h 40m

Chicago Midway

Sat 12/13

4:45 pm-9:55 pm

1 stop4h 10m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

8:40 am-1:15 pm

1 stop5h 35m

Chicago O'Hare Intl

Tue 2/3

8:52 am-2:31 pm

1 stop4h 39m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 1/26

2:35 pm-11:57 pm

2 stops10h 22m

Chicago O'Hare Intl

Mon 2/2

7:01 am-1:45 pm

1 stop5h 44m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

6:00 am-1:11 pm

2 stops8h 11m

Chicago O'Hare Intl

Tue 2/3

1:58 pm-12:20 am

2 stops9h 22m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/30

2:35 pm-11:57 pm

2 stops10h 22m

Chicago O'Hare Intl

Tue 2/3

1:58 pm-11:22 pm

2 stops8h 24m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 1/6

6:00 am-4:43 pm

2 stops11h 43m

Chicago O'Hare Intl

Sat 1/10

11:05 am-10:29 pm

2 stops10h 24m

$239

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 1/31

12:48 pm-10:26 pm

2 stops10h 38m

Chicago Midway

Tue 2/3

1:28 pm-11:22 pm

2 stops8h 54m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 12/3

4:43 pm-8:38 pm

1 stop4h 55m

Chicago O'Hare Intl

Sun 12/7

6:45 am-12:13 pm

1 stop4h 28m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 44 results
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Compare providers for flights from Portland to Chicago

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 Portland to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Portland, Maine-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Chicago 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 Portland, Maine-Chicago 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 Portland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland 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 Portland to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on November 7, 2025.

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $89). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $123). 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 PWM to CHI?

Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

One of the essential ways to save on airfare from Portland, Maine to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 26% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on November 2, 2025.

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

Weekly flight availability from Portland, Maine to Chicago

Explore weekly flight availability from Portland to Chicago. 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 November 13, 2025.

The most flights from PWM to CHI are scheduled on a Wednesday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 13, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Portland to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Chicago. 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 from for flights from Portland to Chicago?

    For a flight from Portland to Chicago, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 3 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Portland on a regular basis.

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

    For as low as $229, United Airlines can have you in Chicago from Portland, Maine in 5h 40m. There are 892 mi between Portland, Maine and Chicago. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Portland, Maine to Chicago round-trip from $124. Other airlines that can offer you cheap pricing are American Airlines, from $203, and United Airlines, from $229. These flights start at 65% lower than the current average price 3 months from now.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Chicago on time: Republic Airways (91%), United Airlines (80%), Air New Zealand (71%).

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

    On average you can expect to pay $964 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $125 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $209.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Chicago 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 Portland, Maine to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $89). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $123). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top 4 airlines flying from Portland to Chicago

Discover the top 4 airlines that operate flights from Portland to Chicago. 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$203Average$304FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$375FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$390FlexibilityNo cancel feeOn-time63%

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