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$149+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Jun 25 — Jul 21
Thu 6/25
Thu 7/2
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago are usually found in September or May, booked 58 days in advance, depart on a Wednesday or Friday and return on a Saturday

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 May 26, 2026.

This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Sat 7/411:00 am
ORD
-
PWM
Nonstop2h 31m
United Airlines
Deal found 5/25$287
This Southwest deal was found by Cheapflights users on 5/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:30 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Sat 7/47:40 am
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 5/25$287
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Fri 7/36:09 am
PWM
-
ORD
Nonstop3h 11m
American Airlines
Tue 7/79:09 pm
ORD
-
PWM
Nonstop2h 34m
American Airlines
Deal found 5/25$292
This Southwest deal was found by Cheapflights users on 5/22. 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 7/37:40 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Tue 7/76:15 pm
MDW
-
PWM
Nonstop2h 20m
Southwest
Deal found 5/22$292
This Delta deal was found by Cheapflights users on 5/21. 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 7/35:41 pm
PWM
-
ORD
1 stop6h 07m
Delta
Sat 7/47:01 am
ORD
-
PWM
1 stop4h 16m
Delta
Deal found 5/21$307
This Delta deal was found by Cheapflights users on 5/21. 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 7/111:48 am
PWM
-
MDW
1 stop7h 30m
Delta
Fri 7/34:25 pm
MDW
-
PWM
1 stop5h 40m
Delta
Deal found 5/21$307
This Delta deal was found by Cheapflights users on 5/21. 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 6/306:25 am
PWM
-
ORD
2 stops8h 51m
Delta
Sat 7/47:01 am
ORD
-
PWM
1 stop4h 16m
Delta
Deal found 5/21$312
This Delta deal was found by Cheapflights users on 5/21. 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 7/111:48 am
PWM
-
MDW
1 stop7h 30m
Delta
Sat 7/410:55 am
MDW
-
PWM
2 stops9h 40m
Delta
Deal found 5/21$312
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Mon 9/72:10 pm
ORD
-
PWM
Nonstop2h 44m
United Airlines
Deal found 5/25$313
This Southwest deal was found by Cheapflights users on 5/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:40 pm
PWM
-
MDW
Nonstop2h 35m
Southwest
Mon 9/76:10 pm
MDW
-
PWM
Nonstop2h 20m
Southwest
Deal found 5/25$313
This Delta deal was found by Cheapflights users on 5/25. 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 7/1511:01 am
PWM
-
ORD
1 stop6h 29m
Delta
Tue 7/215:35 pm
ORD
-
PWM
1 stop4h 55m
Delta
Deal found 5/25$317
This Delta deal was found by Cheapflights users on 5/21. 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 6/306:25 am
PWM
-
MDW
2 stops10h 15m
Delta
Sat 7/41:49 pm
MDW
-
PWM
2 stops10h 03m
Delta
Deal found 5/21$317

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 May 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(United Airlines)

One-way from

$149
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$318

Good round-trip deal

$378 or less

Good one-way deal

$174 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.
Search Deals
From Portland to Chicago (CHI)
Search Deals
One-way flight from Portland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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).
Search Deals

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 May 26, 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

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 8/25

5:03 pm-7:00 pm

Nonstop2h 57m

Chicago O'Hare Intl

Tue 9/1

8:45 am-2:38 pm

1 stop4h 53m

$317

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/22

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Tue 7/28

12:41 pm-11:30 pm

2 stops9h 49m

$332

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/26

6:30 am-1:13 pm

2 stops7h 43m

Chicago O'Hare Intl

Sat 8/29

5:28 am-2:17 pm

2 stops7h 49m

$337

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 9/5

12:20 pm-7:20 pm

1 stop8h 00m

Chicago Midway

Mon 9/7

6:10 pm-9:30 pm

Nonstop2h 20m

$349

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/22

6:05 am-12:40 pm

1 stop7h 35m

Chicago O'Hare Intl

Wed 8/26

1:50 pm-12:59 am

2 stops10h 09m

$358

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/29

7:10 pm-11:15 pm

1 stop5h 05m

Chicago Midway

Sun 8/2

7:55 pm-11:15 pm

Nonstop2h 20m

$364

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 9/16

7:45 am-9:20 am

Nonstop2h 35m

Chicago Midway

Sun 9/20

5:00 am-10:35 am

1 stop4h 35m

$364

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/8

6:25 am-4:15 pm

2 stops10h 50m

Chicago Midway

Mon 7/13

9:19 am-4:01 pm

1 stop5h 42m

$374

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 6/13

6:00 am-1:53 pm

2 stops8h 53m

Chicago O'Hare Intl

Tue 6/16

12:27 pm-11:29 pm

2 stops10h 02m

$377

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 10/14

6:00 am-4:25 pm

2 stops11h 25m

Chicago Midway

Sat 10/17

9:30 am-4:10 pm

1 stop5h 40m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 41 resultsSorted by cheapest first
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2
3
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5

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust 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

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 $130). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $209). 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 May 26, 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 morning tend to be the most expensive. A flight at noon could potentially save you up to 22% 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 May 26, 2026.

The most flights from PWM to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Portland, Maine to Chicago?

How far ahead should I book a flight from Portland, Maine to Chicago?

Booking 83 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.

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 May 26, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,749 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,629 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 3 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 $329, Delta can have you in Chicago from Portland, Maine in 3h. 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 $209. Other airlines that can offer you cheap pricing are United Airlines, from $239, and Southwest, from $267. These flights start at 40% 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 Delta. According to our data, you can fly for as low as $114. Users have also found prices from $115 and $134 on American Airlines 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: United Airlines (88%), American Airlines (85%), Envoy Air (85%).

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

    On average you can expect to pay $935 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $134 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $287.

  • 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 $130). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $209). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 3 airlines flying from Portland to Chicago

Discover the top 3 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 May 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$309FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$358FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$267Average$397FlexibilityNo cancel feeOn-time63%

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