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$66+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
ene. 25 — feb. 11
sáb. 1/25
sáb. 2/1
1 adult, Economy
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The best prices from Portland to Chicago are usually found in September or August, booked 39 days in advance, depart on a Thursday or Wednesday 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 enero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(United Airlines)

One-way from

$66
(CheapOair)

Popular in

April

Cheapest in

September

Average price

$347
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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High demand for flights, 17% potential price rise
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Best time to find cheap flights, 4% potential price drop
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Average for round-trip flights in January 2025
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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 enero 20, 2025.

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.
vie. 2/76:00 amPWM - ORD
1 stop5h 44mUnited Airlines
lun. 2/103:15 pmORD - PWM
1 stop6h 15mUnited Airlines
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.
vie. 2/76:00 amPWM - ORD
2 stops10h 45mDelta
lun. 2/104:55 pmORD - PWM
1 stop6h 00mDelta
Deal found 1/20$244
This Delta deal was found by Cheapflights users on 1/19. 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.
vie. 3/287:00 amPWM - MDW
1 stop6h 36mDelta
dom. 3/306:42 pmMDW - PWM
1 stop3h 32mDelta
Deal found 1/19$254
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.
mié. 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
lun. 7/146:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 1/20$258
This JetBlue 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/46:10 amPWM - ORD
1 stop7h 19mJetBlue
vie. 4/111:22 pmORD - PWM
1 stop8h 38mJetBlue
Deal found 1/20$273
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.
jue. 1/303:35 pmPWM - ORD
1 stop7h 45mSouthwest
mié. 2/54:35 pmORD - PWM
1 stop4h 40mSouthwest
Deal found 1/20$279
This FlightHub deal was found by Cheapflights users on 1/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/89:29 pmPWM - MDW
1 stop15h 55mFrontier
dom. 5/119:00 amMDW - PWM
1 stop10h 29mFrontier
Deal found 1/19$286
This Southwest deal was found by Cheapflights users on 1/19. 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.
mié. 2/121:05 pmPWM - MDW
1 stop9h 20mSouthwest
vie. 2/142:40 pmMDW - PWM
1 stop8h 15mSouthwest
Deal found 1/19$299
This Mytrip deal was found by Cheapflights users on 1/19. 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.
mar. 3/46:07 pmPWM - ORD
3 stops40h 22mMultiple Airlines
mar. 3/117:42 pmORD - PWM
2 stops22h 45mMultiple Airlines
Deal found 1/19$400

Find flights from Portland to Chicago within your budget

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 enero 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

sáb. 5/24

5:00 pm-8:34 pm

1 stop4h 34m

Chicago O'Hare Intl

mar. 5/27

7:00 am-11:54 am

1 stop3h 54m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 4/4

6:00 am-10:48 am

1 stop5h 48m

Chicago O'Hare Intl

lun. 4/14

7:30 am-11:02 am

Nonstop2h 32m

$241

PortlandChicago

PWM - ORD

PWMORD

Portland

dom. 2/23

5:45 am-10:50 am

1 stop6h 05m

Chicago O'Hare Intl

vie. 2/28

6:06 am-11:47 am

1 stop4h 41m

$243

PortlandChicago

PWM - MDW

PWMMDW

Portland

vie. 3/28

7:00 am-12:36 pm

1 stop6h 36m

Chicago Midway

dom. 3/30

6:42 pm-11:14 pm

1 stop3h 32m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

dom. 2/23

5:35 am-2:00 pm

1 stop9h 25m

Chicago O'Hare Intl

sáb. 3/1

1:30 pm-11:15 pm

2 stops8h 45m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 4/4

6:10 am-12:29 pm

1 stop7h 19m

Chicago O'Hare Intl

vie. 4/11

1:22 pm-11:00 pm

1 stop8h 38m

$273

PortlandChicago

PWM - MDW

PWMMDW

Portland

jue. 5/8

9:29 pm-12:24 pm

1 stop15h 55m

Chicago Midway

dom. 5/11

9:00 am-8:29 pm

1 stop10h 29m

$286

PortlandChicago

PWM - MDW

PWMMDW

Portland

mié. 2/12

1:05 pm-9:25 pm

1 stop9h 20m

Chicago Midway

vie. 2/14

2:40 pm-11:55 pm

1 stop8h 15m

$299

PortlandChicago

PWM - ORD

PWMORD

Portland

mar. 3/4

6:07 pm-9:29 am

3 stops40h 22m

Chicago O'Hare Intl

mar. 3/11

7:42 pm-7:27 pm

2 stops22h 45m

$400

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 5/1

9:29 pm-11:32 pm

1 stop27h 03m

$66

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 21 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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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.

Travel insights for flights from Portland to Chicago

Get recent, data-driven insights about flights from Portland to Chicago including ideal travel times, pricing trends, and more.

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 17, 2025.

Booking 39 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 $320). 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 enero 20, 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 65% 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 December 16, 2024.

Travelers seeking maximum savings on their Portland, Maine to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons 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 enero 20, 2025.

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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 73.4 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 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 enero 20, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines and Southwest from Portland to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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
4,659 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

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 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. 5 airlines have flights to Chicago from Portland on a regular basis.

  • 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 $241. Other airlines that can offer you cheap pricing are American Airlines, from $243, and Delta, from $249. These flights start at 36% 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 Frontier. According to our data, you can fly for as low as $66. Users have also found prices from $115 and $115 on Delta and Southwest, 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: Air New Zealand (90%), Republic Airways (89%), United Airlines (88%).

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

    On average you can expect to pay $533 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $213 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $172.

  • 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 $320). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 5 airlines flying from Portland to Chicago

Discover the top 5 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 enero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$110FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$353FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$397FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$208Average$410FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$390FlexibilityNo cancel feeOn-time63%
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