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$88+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago are usually found in September or May, booked 43 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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Southwest)

One-way from

$88
(Southwest)

Popular in

December

Cheapest in

September

Average price

$352

Good round-trip deal

$372 or less

Good one-way deal

$263 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
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. 9% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago (CHI).
Search Deals
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 January 8, 2026.

This Southwest deal was found by Cheapflights users on 1/7. 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.
Wed 1/2812:45 pmPWM - MDW
1 stop7h 15mSouthwest
Thu 1/296:50 amMDW - PWM
1 stop7h 05mSouthwest
Deal found 1/7$193
This Delta deal was found by Cheapflights users on 1/7. 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 2/36:00 amPWM - ORD
1 stop5h 55mDelta
Tue 2/102:50 pmORD - PWM
1 stop6h 37mDelta
Deal found 1/7$197
This Delta deal was found by Cheapflights users on 1/7. 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 2/312:10 pmPWM - MDW
1 stop6h 45mDelta
Wed 2/1110:46 amMDW - PWM
2 stops11h 36mDelta
Deal found 1/7$202
This Delta deal was found by Cheapflights users on 1/7. 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.
Mon 2/212:10 pmPWM - ORD
1 stop5h 28mDelta
Wed 2/115:40 pmORD - PWM
1 stop4h 42mDelta
Deal found 1/7$204
This Delta deal was found by Cheapflights users on 1/7. 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 2/45:30 amPWM - ORD
2 stops12h 27mDelta
Tue 2/1011:15 amORD - PWM
2 stops11h 07mDelta
Deal found 1/7$208
This Southwest deal was found by Cheapflights users on 1/7. 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.
Wed 1/285:45 amPWM - MDW
2 stops9h 10mSouthwest
Fri 1/309:50 amMDW - PWM
1 stop4h 05mSouthwest
Deal found 1/7$208
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Fri 5/85:45 pmPWM - ORD
Nonstop3h 10mAmerican Airlines
Mon 5/117:34 pmORD - PWM
Nonstop2h 36mAmerican Airlines
Deal found 1/7$209
This Delta deal was found by Cheapflights users on 1/7. 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 2/35:30 amPWM - MDW
1 stop7h 29mDelta
Mon 2/91:26 pmMDW - PWM
2 stops8h 56mDelta
Deal found 1/7$209
This Delta deal was found by Cheapflights users on 1/8. 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.
Mon 2/22:35 pmPWM - ORD
1 stop8h 00mDelta
Thu 2/56:50 amORD - PWM
1 stop4h 13mDelta
Deal found 1/8$211
This Delta deal was found by Cheapflights users on 1/7. 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 2/312:43 pmPWM - ORD
1 stop6h 45mDelta
Fri 2/137:00 amORD - PWM
1 stop5h 43mDelta
Deal found 1/7$213
This Delta deal was found by Cheapflights users on 1/6. 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 4/85:18 amPWM - MDW
1 stop7h 44mDelta
Sun 4/129:35 amMDW - PWM
1 stop5h 31mDelta
Deal found 1/6$213
This Delta deal was found by Cheapflights users on 1/8. 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.
Mon 3/94:48 pmPWM - ORD
2 stops8h 11mDelta
Wed 3/117:10 amORD - PWM
2 stops5h 40mDelta
Deal found 1/8$215

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 January 8, 2026.
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 2/17

6:18 am-1:29 pm

1 stop8h 11m

Chicago O'Hare Intl

Wed 2/18

6:25 pm-12:18 am

1 stop4h 53m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/17

6:18 am-1:29 pm

1 stop8h 11m

Chicago O'Hare Intl

Tue 2/24

6:30 am-12:00 pm

1 stop4h 30m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/11

5:59 pm-10:34 pm

1 stop5h 35m

Chicago O'Hare Intl

Tue 2/24

5:20 pm-11:20 pm

1 stop5h 00m

$197

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/28

5:45 am-1:55 pm

2 stops9h 10m

Chicago Midway

Thu 1/29

6:50 am-2:55 pm

1 stop7h 05m

$199

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/4

12:10 pm-5:55 pm

1 stop6h 45m

Chicago Midway

Tue 2/10

12:46 pm-12:20 am

2 stops10h 34m

$202

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/18

12:13 pm-5:37 pm

1 stop6h 24m

Chicago Midway

Wed 2/25

12:45 pm-12:18 am

2 stops10h 33m

$202

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 2/3

5:30 am-11:59 am

1 stop7h 29m

Chicago Midway

Tue 2/10

1:26 pm-11:22 pm

2 stops8h 56m

$202

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/4

6:00 am-12:51 pm

2 stops7h 51m

Chicago Midway

Wed 2/11

12:46 pm-11:22 pm

2 stops9h 36m

$208

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/2

4:48 pm-6:45 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 7/5

1:55 pm-5:12 pm

Nonstop2h 17m

$209

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 2/3

5:30 am-11:59 am

1 stop7h 29m

Chicago Midway

Mon 2/9

1:26 pm-11:22 pm

2 stops8h 56m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 41 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 January.
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 January 2, 2026.

Booking 43 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 $122). 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 January 8, 2026.

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.

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 January 8, 2026.

The most flights from PWM to CHI 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).

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 January 8, 2026.
See what other customers who have flown with Southwest, United Airlines, and American 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
4,250 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
9,139 reviews
Southwest
8.0
Very good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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
11,094 reviews
Southwest
8.0
Very good
4,250 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

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 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 2 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 $209, Delta can have you in Chicago from Portland, Maine in 2h 57m. 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 $114. Other airlines that can offer you cheap pricing are American Airlines, from $209, and United Airlines, from $228. These flights start at 67% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Portland, Maine to Chicago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $104. Users have also found prices from $114 and $115 on Delta and United Airlines, respectively.

  • 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: Qatar Airways (100%), Republic Airways (85%), United Airlines (74%).

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

    On average you can expect to pay $500 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $140 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $197.

  • 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 $122). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$208Average$306FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$374FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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