Chicago

$77+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Mar 29 — Apr 51
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Find cheap flights from Portland to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Portland to Chicago are usually found in April or September, booked 70 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 February 27, 2026.

This Delta deal was found by Cheapflights users on 2/24. 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 4/86:03 am
PWM
-
ORD
2 stops8h 14m
Delta
Fri 4/102:32 pm
ORD
-
PWM
1 stop7h 50m
Delta
Deal found 2/24$209
This Delta deal was found by Cheapflights users on 2/25. 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.
Thu 5/712:55 pm
PWM
-
MDW
1 stop6h 38m
Delta
Sun 5/106:23 am
MDW
-
PWM
1 stop5h 47m
Delta
Deal found 2/25$213
This Delta deal was found by Cheapflights users on 2/26. 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 4/86:03 am
PWM
-
MDW
2 stops7h 26m
Delta
Fri 4/101:10 pm
MDW
-
PWM
2 stops9h 12m
Delta
Deal found 2/26$214
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/147:33 pm
PWM
-
ORD
1 stop5h 10m
United Airlines
Sat 4/186:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 2/23$219
This Delta deal was found by Cheapflights users on 2/23. 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.
Fri 5/84:48 pm
PWM
-
ORD
1 stop4h 26m
Delta
Sun 5/106:00 am
ORD
-
PWM
1 stop6h 10m
Delta
Deal found 2/23$220
This Delta deal was found by Cheapflights users on 2/23. 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 4/145:26 pm
PWM
-
ORD
1 stop5h 49m
Delta
Sat 4/186:04 am
ORD
-
PWM
1 stop7h 07m
Delta
Deal found 2/23$224
This Delta deal was found by Cheapflights users on 2/24. 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.
Fri 5/2212:55 pm
PWM
-
ORD
1 stop6h 10m
Delta
Sun 5/247:00 am
ORD
-
PWM
1 stop4h 00m
Delta
Deal found 2/24$229
This American Airlines deal was found by Cheapflights users on 2/25. 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 4/77:23 pm
PWM
-
ORD
1 stop5h 11m
American Airlines
Sun 4/127:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 2/25$230
This Delta deal was found by Cheapflights users on 2/25. 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 4/75:48 pm
PWM
-
ORD
1 stop5h 24m
Delta
Sun 4/127:10 am
ORD
-
PWM
1 stop3h 59m
Delta
Deal found 2/25$233
This Delta deal was found by Cheapflights users on 2/26. 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 4/112:51 pm
PWM
-
MDW
1 stop6h 03m
Delta
Mon 4/61:10 pm
MDW
-
PWM
2 stops9h 02m
Delta
Deal found 2/26$234
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Wed 7/84:51 pm
PWM
-
ORD
Nonstop3h 00m
United Airlines
Sat 7/116:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 2/26$237
This Delta deal was found by Cheapflights users on 2/25. 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 4/86:03 am
PWM
-
ORD
2 stops8h 14m
Delta
Sun 4/127:10 am
ORD
-
PWM
1 stop3h 59m
Delta
Deal found 2/25$238

Find 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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Delta)

One-way from

$77
(JetBlue)

Popular in

December

Cheapest in

April

Average price

$389

Good round-trip deal

$348 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
From Portland to Chicago (CHI)
One-way flight from Portland to Chicago (CHI)
Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in February 2026
Price to beat on a round-trip flight from Portland to Chicago (CHI).
Price to beat on a one-way flight from Portland to Chicago (CHI).

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 February 27, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 5/7

12:55 pm-6:33 pm

1 stop6h 38m

Chicago Midway

Sun 5/10

6:23 am-1:10 pm

1 stop5h 47m

$213

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/7

7:10 pm-11:44 pm

1 stop5h 34m

Chicago O'Hare Intl

Sun 5/10

7:15 am-10:53 am

Nonstop2h 38m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:55 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/28

9:30 am-6:01 pm

1 stop7h 31m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 4/11

12:51 pm-4:18 pm

1 stop4h 27m

Chicago O'Hare Intl

Sun 4/12

7:10 am-12:09 pm

1 stop3h 59m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 3/28

4:48 pm-8:17 pm

1 stop4h 29m

Chicago O'Hare Intl

Tue 3/31

1:57 pm-11:12 pm

2 stops8h 15m

$300

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 8/20

11:38 am-6:05 pm

1 stop7h 27m

Chicago Midway

Sun 8/23

6:00 am-12:22 pm

1 stop5h 22m

$304

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 4/10

4:50 pm-10:20 pm

1 stop6h 30m

Chicago Midway

Mon 4/13

2:10 pm-11:25 pm

2 stops8h 15m

$311

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/14

11:42 am-8:40 pm

2 stops9h 58m

Chicago O'Hare Intl

Sun 4/19

1:36 pm-12:46 am

2 stops10h 10m

$339

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/10

12:51 pm-6:34 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 4/15

5:04 pm-12:46 am

2 stops6h 42m

$339

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/18

5:20 pm-12:40 am

2 stops8h 20m

Chicago Midway

Sun 6/21

7:55 pm-11:10 pm

Nonstop2h 15m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 February 20, 2026.

Booking 70 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, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $91). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $123). 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 February 27, 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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 41% 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 February 27, 2026.

The most flights from PWM to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 February 27, 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.

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 4 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 $219, Delta can have you in Chicago from Portland, Maine in 5h 34m. 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 $223. 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: American Airlines (100%), Envoy Air (100%), Republic Airways (97%).

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

    On average you can expect to pay $1,127 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $143 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $204.

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $91). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $123). 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 February 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$351FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$305FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$223Average$370FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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