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$124+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$226
(Trip.com)

One-way from

$124
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$283

Good round-trip deal

$318 or less

Good one-way deal

$177 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. 13% potential increase in price ($58 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 September 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 September 29, 2025.

This Trip.com deal was found by Cheapflights users on 9/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:09 amPWM - ORD
1 stop6h 13mJetBlue
Thu 10/231:35 pmORD - PWM
1 stop8h 29mJetBlue
Deal found 9/28$226
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/284:51 pmPWM - ORD
Nonstop3h 01mUnited Airlines
Tue 11/412:00 pmORD - PWM
1 stop4h 48mUnited Airlines
Deal found 9/28$257
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/2512:59 pmPWM - ORD
1 stop9h 20mAmerican Airlines
Tue 10/2811:13 amORD - PWM
1 stop8h 01mAmerican Airlines
Deal found 9/27$263
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Tue 11/45:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Tue 11/111:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Deal found 9/27$265
This Delta deal was found by Cheapflights users on 9/28. 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 11/51:46 pmPWM - ORD
1 stop6h 39mDelta
Wed 11/126:45 amORD - PWM
1 stop4h 23mDelta
Deal found 9/28$267
This Delta deal was found by Cheapflights users on 9/28. 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 11/1112:48 pmPWM - MDW
1 stop6h 20mDelta
Wed 11/129:34 amMDW - PWM
1 stop5h 33mDelta
Deal found 9/28$267
This JetBlue deal was found by Cheapflights users on 9/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:09 amPWM - ORD
1 stop6h 13mJetBlue
Tue 10/211:35 pmORD - PWM
1 stop8h 29mJetBlue
Deal found 9/29$269
This Delta deal was found by Cheapflights users on 9/27. 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 11/512:45 pmPWM - MDW
1 stop6h 40mDelta
Wed 11/121:15 pmMDW - PWM
2 stops9h 39mDelta
Deal found 9/27$272
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/275:59 pmPWM - ORD
1 stop6h 54mAmerican Airlines
Wed 10/297:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 9/28$275
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/35:21 pmPWM - ORD
1 stop5h 02mAmerican Airlines
Wed 11/51:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Deal found 9/27$276
This Delta deal was found by Cheapflights users on 9/27. 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 11/511:30 amPWM - ORD
2 stops8h 19mDelta
Tue 11/1111:19 amORD - PWM
2 stops11h 35mDelta
Deal found 9/27$277
This Delta deal was found by Cheapflights users on 9/27. 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 11/51:46 pmPWM - MDW
2 stops9h 28mDelta
Tue 11/111:15 pmMDW - PWM
2 stops9h 39mDelta
Deal found 9/27$277

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 September 29, 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

Tue 11/11

6:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

Wed 11/12

6:45 am-12:08 pm

1 stop4h 23m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 11/4

3:20 pm-9:16 pm

1 stop6h 56m

Chicago O'Hare Intl

Tue 11/11

5:31 pm-11:17 pm

1 stop4h 46m

$267

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 11/11

12:48 pm-6:08 pm

1 stop6h 20m

Chicago Midway

Wed 11/12

9:34 am-4:07 pm

1 stop5h 33m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 10/15

7:09 am-12:22 pm

1 stop6h 13m

Chicago O'Hare Intl

Tue 10/21

1:35 pm-11:04 pm

1 stop8h 29m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 11/4

1:46 pm-8:37 pm

1 stop7h 51m

Chicago O'Hare Intl

Tue 11/11

11:19 am-11:54 pm

2 stops11h 35m

$272

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 11/12

2:30 pm-9:27 pm

1 stop7h 57m

Chicago O'Hare Intl

Wed 11/19

1:29 pm-11:54 pm

2 stops9h 25m

$272

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 11/4

12:45 pm-6:25 pm

1 stop6h 40m

Chicago Midway

Tue 11/11

1:15 pm-11:19 pm

2 stops9h 04m

$272

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/12

6:00 am-11:52 am

1 stop6h 52m

Chicago Midway

Wed 11/19

1:15 pm-11:19 pm

2 stops9h 04m

$272

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 10/27

5:59 pm-11:53 pm

1 stop6h 54m

Chicago O'Hare Intl

Wed 10/29

11:30 am-2:56 pm

Nonstop2h 26m

$275

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/5

1:46 pm-10:14 pm

2 stops9h 28m

Chicago Midway

Wed 11/12

1:15 pm-11:19 pm

2 stops9h 04m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 42 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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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 September 26, 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, August is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $245). Flying from Portland, Maine to Chicago in March is currently the most expensive (average of $321). 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 September 29, 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 morning tend to be the most expensive. A flight in the evening could potentially save you up to 7% 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 September 28, 2025.

Travelers seeking maximum savings on their Portland, Maine to Chicago flight should consider departing on Thursday 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 September 29, 2025.

The most flights from PWM to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 September 29, 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
4,245 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
8,924 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

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 8 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 $267, Delta can have you in Chicago from Portland, Maine in 5h 13m. There are 897 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 $202, and United Airlines, from $229. These flights start at 66% 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: American Airlines (76%), Republic Airways (74%), Air New Zealand (71%).

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

    On average you can expect to pay $646 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $115 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $247.

  • 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, August is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $245). Flying from Portland, Maine to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$381FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$397FlexibilityNo cancel feeOn-time63%

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