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$100+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$230
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$339

Good round-trip deal

$229 or less

Good one-way deal

$207 or less
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 ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3012:08 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Sun 8/318:05 amORD - PWM
Nonstop2h 33mAmerican Airlines
Deal found 8/13$230
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Wed 9/36:00 amORD - PWM
1 stop16h 25mDelta
Deal found 8/13$231
This JetBlue deal was found by Cheapflights users on 8/14. 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.
Sat 8/302:19 pmPWM - ORD
1 stop9h 09mJetBlue
Fri 9/51:36 pmORD - PWM
1 stop7h 26mJetBlue
Deal found 8/14$233
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/306:30 amPWM - ORD
Nonstop3h 02mAmerican Airlines
Thu 9/43:33 pmORD - PWM
1 stop7h 12mAmerican Airlines
Deal found 8/14$239
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3110:25 amPWM - MDW
Nonstop2h 35mSouthwest
Sun 11/25:05 amMDW - PWM
1 stop5h 05mSouthwest
Deal found 8/13$239
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/96:01 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Wed 9/108:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 8/14$241
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Tue 10/71:36 pmORD - PWM
1 stop7h 25mJetBlue
Deal found 8/13$243
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 9/176:15 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Sun 9/218:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 8/12$245
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Tue 9/211:05 amORD - PWM
1 stop5h 43mDelta
Deal found 8/13$249
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:50 amPWM - MDW
1 stop6h 55mSouthwest
Tue 9/232:55 pmMDW - PWM
1 stop6h 30mSouthwest
Deal found 8/13$251
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:50 pmPWM - MDW
Nonstop2h 35mSouthwest
Sun 8/315:55 pmMDW - PWM
Nonstop2h 20mSouthwest
Deal found 8/13$253
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 8/276:00 amPWM - ORD
2 stops7h 45mDelta
Sun 8/315:45 amORD - PWM
1 stop5h 44mDelta
Deal found 8/13$254

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 August 14, 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

Sat 8/30

12:08 pm-2:10 pm

Nonstop3h 02m

Chicago O'Hare Intl

Sun 8/31

8:05 am-11:38 am

Nonstop2h 33m

$230

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

Chicago O'Hare Intl

Wed 9/3

6:00 am-11:25 pm

1 stop16h 25m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 9/23

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Tue 9/23

1:55 pm-5:42 pm

Nonstop2h 47m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

1:34 pm-7:19 pm

1 stop6h 45m

Chicago O'Hare Intl

Mon 9/1

6:00 am-11:25 pm

1 stop16h 25m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 9/3

7:30 am-12:10 pm

1 stop5h 40m

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

$233

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

10:25 am-12:00 pm

Nonstop2h 35m

Chicago Midway

Sun 11/2

5:05 am-11:10 am

1 stop5h 05m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/31

6:29 am-8:23 am

Nonstop2h 54m

Chicago O'Hare Intl

Sun 11/2

5:05 am-10:49 am

1 stop4h 44m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

6:30 am-8:32 am

Nonstop3h 02m

Chicago O'Hare Intl

Thu 9/4

3:33 pm-11:45 pm

1 stop7h 12m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 9/30

12:21 pm-2:14 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 10/1

7:00 am-12:29 pm

1 stop4h 29m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 37 results
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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 August 8, 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 August 14, 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 12% 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 August 10, 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 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 August 14, 2025.

The most flights from PWM to CHI are scheduled on a Thursday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 August 14, 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
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 7 outbound flights to Chicago per day. 4 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 $124. Other airlines that can offer you cheap pricing are American Airlines, from $199, and United Airlines, from $233. These flights start at 66% 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 $100. Users have also found prices from $100 and $102 on Southwest and JetBlue, 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: Envoy Air (97%), American Airlines (91%), SkyWest Airlines (80%).

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

    On average you can expect to pay $962 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 $183.

  • 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$199Average$311FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$390FlexibilityNo cancel feeOn-time63%

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