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Portland

$67+ Cheap flights from Chicago (CHI) to Portland, ME (PWM)

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Portland are usually found in February or March, booked 68 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PWM). 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 September 11, 2025.

Round-trip from

$242
(Southwest)

One-way from

$67
(United Airlines)

Popular in

December

Cheapest in

February

Average price

$323

Good round-trip deal

$272 or less

Good one-way deal

$194 or less
From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Portland.
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Price to beat on a one-way flight from Chicago (CHI) to Portland.
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Find flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2111:25 amORD - PWM
2 stops10h 05mSouthwest
Sat 10/255:50 amPWM - ORD
1 stop7h 00mSouthwest
Deal found 9/11$242
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:55 amMDW - PWM
Nonstop2h 10mSouthwest
Thu 10/232:40 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 9/9$242
This Trip.com deal was found by Cheapflights users on 9/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:35 pmORD - PWM
1 stop8h 29mJetBlue
Tue 10/217:09 amPWM - ORD
1 stop6h 13mJetBlue
Deal found 9/11$244
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/12:20 pmORD - PWM
1 stop7h 53mUnited Airlines
Fri 10/36:25 pmPWM - ORD
Nonstop3h 00mUnited Airlines
Deal found 9/10$245
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Tue 9/305:41 pmPWM - ORD
1 stop6h 49mUnited Airlines
Deal found 9/11$246
This Southwest deal was found by Cheapflights users on 9/10. 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 12/1611:55 amORD - PWM
2 stops9h 20mSouthwest
Tue 1/1312:45 pmPWM - ORD
2 stops10h 05mSouthwest
Deal found 9/10$247
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:45 amORD - PWM
1 stop9h 53mAmerican Airlines
Tue 10/216:00 amPWM - ORD
1 stop6h 06mAmerican Airlines
Deal found 9/10$250
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 12/59:34 amMDW - PWM
1 stop5h 32mDelta
Mon 12/82:34 pmPWM - MDW
2 stops9h 58mDelta
Deal found 9/10$250
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:49 amORD - PWM
1 stop5h 06mAmerican Airlines
Tue 10/76:00 amPWM - ORD
1 stop6h 06mAmerican Airlines
Deal found 9/10$251
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/16:28 pmORD - PWM
1 stop5h 06mDelta
Wed 10/86:00 amPWM - ORD
2 stops11h 11mDelta
Deal found 9/10$253
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amORD - PWM
1 stop6h 53mUnited Airlines
Wed 10/87:25 pmPWM - ORD
1 stop4h 50mUnited Airlines
Deal found 9/11$255
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/61:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Sun 11/95:43 amPWM - ORD
1 stop6h 15mAmerican Airlines
Deal found 9/11$256

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Portland 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 10/20

10:55 am-2:05 pm

Nonstop2h 10m

Portland

Thu 10/23

2:40 pm-4:15 pm

Nonstop2h 35m

$242

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/8

9:00 am-4:44 pm

1 stop6h 44m

Portland

Mon 10/13

6:14 am-8:05 am

Nonstop2h 51m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 12/13

5:25 pm-11:12 pm

1 stop4h 47m

Portland

Tue 1/13

4:10 pm-6:24 pm

Nonstop3h 14m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 12/16

11:55 am-10:15 pm

2 stops9h 20m

Portland

Tue 1/13

12:45 pm-9:50 pm

2 stops10h 05m

$247

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

6:28 pm-12:34 am

1 stop5h 06m

Portland

Wed 10/8

6:00 am-4:11 pm

2 stops11h 11m

$253

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

1:25 pm-10:19 pm

2 stops7h 54m

Portland

Sat 10/25

6:30 am-12:40 pm

2 stops7h 10m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 12/17

5:25 pm-11:09 pm

1 stop4h 44m

Portland

Tue 1/13

6:00 am-1:15 pm

1 stop8h 15m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 11/13

10:53 am-2:12 pm

Nonstop2h 19m

Portland

Sun 11/16

5:30 am-9:46 am

1 stop5h 16m

$255

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 10/28

10:05 am-7:55 pm

2 stops8h 50m

Portland

Sat 11/1

10:45 am-5:00 pm

2 stops7h 15m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/26

6:28 pm-12:34 am

1 stop5h 06m

Portland

Wed 10/1

6:00 am-4:31 pm

2 stops11h 31m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 41 results
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Best time to book a flight from Chicago to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago 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 Chicago to Portland

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago to Portland, Maine is 68 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $296). Flying from Chicago to Portland, Maine in July is currently the most expensive (average of $394). 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 CHI to PWM?

Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 16% on airfare.

What is the cheapest day to fly from Chicago to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Portland, Maine

Explore weekly flight availability from Chicago to Portland. 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 September 11, 2025.

The most flights from CHI to PWM are scheduled on a Monday (12 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 on average).

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

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portland. 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 into for flights to Portland from Chicago?

    Most people fly into Portland (PWM) if they book a flight to Portland from Chicago. On average, Portland has 11 inbound flights from Chicago per day from 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Chicago to Portland, Maine?

    There are many flights that can get you from Chicago to Portland, Maine in 2h 10m. Fly via Southwest, United Airlines, or Delta to get the fastest option. There are 892 mi between Chicago and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Portland, Maine round-trip?

    Delta, at $163, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Delta is 54% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Chicago to Portland, Maine?

    No one likes to see their flight delayed. When booking a flight from Chicago to Portland, Maine consider choosing Envoy Air (100%), SkyWest Airlines (74%) or United Airlines (72%) as they are the most reliable in getting you off to your destination on time.

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

    Looking for the cheapest flight from Chicago to Portland, Maine? While on average our users pay $281, our data indicates the cheapest price to be $129. The most popular route (Chicago O'Hare Intl - Portland), is priced around $133.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland 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 Chicago to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $296). Flying from Chicago to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Portland

Discover the top 4 airlines that operate flights from Chicago to Portland. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$387FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$231Average$351FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$276Average$411FlexibilityNo cancel feeOn-time63%

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