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$90+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago are usually found in September or August, booked 85 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 June 12, 2025.

Round-trip from

$219
(American Airlines)

One-way from

$90
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$366

Good round-trip deal

$314 or less

Good one-way deal

$173 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. 12% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 6/266:00 amPWM - ORD
Nonstop2h 57mAmerican Airlines
Mon 6/307:09 pmORD - PWM
Nonstop2h 38mAmerican Airlines
Deal found 6/11$219
This United Airlines deal was found by Cheapflights users on 6/10. 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 7/110:05 amPWM - ORD
1 stop7h 47mUnited Airlines
Wed 7/96:30 pmORD - PWM
Nonstop2h 31mUnited Airlines
Deal found 6/10$229
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/22:19 pmPWM - ORD
1 stop9h 09mJetBlue
Tue 8/56:10 amORD - PWM
1 stop6h 13mJetBlue
Deal found 6/11$233
This Delta deal was found by Cheapflights users on 6/10. 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 6/306:56 pmPWM - ORD
1 stop6h 03mDelta
Sat 7/127:00 amORD - PWM
1 stop16h 57mDelta
Deal found 6/10$235
This Southwest deal was found by Cheapflights users on 6/10. 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 7/15:30 amPWM - ORD
1 stop7h 20mSouthwest
Fri 7/111:50 pmORD - PWM
1 stop9h 15mSouthwest
Deal found 6/10$244
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 7/212:49 pmPWM - MDW
1 stop6h 52mDelta
Wed 7/99:25 amMDW - PWM
1 stop5h 46mDelta
Deal found 6/11$248
This Southwest deal was found by Cheapflights users on 6/10. 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 7/226:55 pmPWM - MDW
Nonstop2h 35mSouthwest
Tue 8/511:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 6/10$254
This Sun Country Air deal was found by Cheapflights users on 6/12. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1712:58 pmPWM - ORD
1 stop26h 07mSun Country Air
Wed 7/2312:20 pmORD - PWM
1 stop22h 55mSun Country Air
Deal found 6/12$335
This CheapTicketsDeal deal was found by Cheapflights users on 6/9. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1012:51 pmPWM - MDW
1 stop6h 49mAlaska Airlines
Tue 8/126:04 amMDW - PWM
1 stop5h 25mAlaska Airlines
Deal found 6/9$368
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:05 pmPWM - MDW
1 stop23h 21mFrontier
Sun 10/128:39 amMDW - PWM
1 stop25h 26mFrontier
Deal found 6/10$392
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:05 pmPWM - ORD
1 stop27h 48mFrontier
Sun 10/126:09 pmORD - PWM
1 stop15h 56mFrontier
Deal found 6/10$412
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 7/512:38 pmPWM - ORD
1 stop8h 45mMultiple Airlines
Sun 7/66:45 amORD - PWM
1 stop27h 32mMultiple Airlines
Deal found 6/10$430

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 June 12, 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 6/26

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Mon 6/30

7:09 pm-10:47 pm

Nonstop2h 38m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 7/1

10:05 am-4:52 pm

1 stop7h 47m

Chicago O'Hare Intl

Wed 7/9

6:30 pm-10:01 pm

Nonstop2h 31m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/2

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

Tue 8/5

6:10 am-1:23 pm

1 stop6h 13m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 6/30

6:56 pm-11:59 pm

1 stop6h 03m

Chicago O'Hare Intl

Sat 7/12

7:00 am-12:57 am

1 stop16h 57m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 7/1

5:30 am-11:50 am

1 stop7h 20m

Chicago O'Hare Intl

Fri 7/11

1:50 pm-12:05 am

1 stop9h 15m

$244

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/2

12:49 pm-6:41 pm

1 stop6h 52m

Chicago Midway

Wed 7/9

9:25 am-4:11 pm

1 stop5h 46m

$248

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 7/22

6:55 pm-8:30 pm

Nonstop2h 35m

Chicago Midway

Tue 8/5

11:40 am-2:55 pm

Nonstop2h 15m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/17

12:58 pm-2:05 pm

1 stop26h 07m

Chicago O'Hare Intl

Wed 7/23

12:20 pm-12:15 pm

1 stop22h 55m

$335

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sun 8/10

12:51 pm-6:40 pm

1 stop6h 49m

Chicago Midway

Tue 8/12

6:04 am-12:29 pm

1 stop5h 25m

$368

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/10

12:05 pm-10:26 am

1 stop23h 21m

Chicago Midway

Sun 10/12

8:39 am-11:05 am

1 stop25h 26m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 23 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 June 9, 2025.

Booking 85 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 June 12, 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 50% 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 June 8, 2025.

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 June 12, 2025.

The most flights from PWM to CHI are scheduled on a Tuesday (9 on average). You will have fewer flight options on Saturday, 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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 6 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 $219. Other airlines that can offer you cheap pricing are United Airlines, from $229, and JetBlue, from $233. These flights start at 39% 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 United Airlines. According to our data, you can fly for as low as $90. Users have also found prices from $90 and $97 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: Republic Airways (100%), Qatar Airways (99%), American Airlines (96%).

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

    On average you can expect to pay $796 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $129 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $219.

  • 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$127FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$313FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$373FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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