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Portland

$102+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$238
(American Airlines)

One-way from

$102
(Priceline)

Popular in

December

Cheapest in

February

Average price

$339

Good round-trip deal

$284 or less

Good one-way deal

$156 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 ($38 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 August 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 August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/19. 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 9/310:05 amORD - PWM
1 stop9h 06mAmerican Airlines
Sat 9/68:40 amPWM - ORD
1 stop11h 21mAmerican Airlines
Deal found 8/19$238
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/317:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Sun 11/25:41 amPWM - ORD
1 stop6h 17mAmerican Airlines
Deal found 8/19$239
This United Airlines deal was found by Cheapflights users on 8/18. 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 10/184:05 pmORD - PWM
1 stop6h 15mUnited Airlines
Wed 10/224:57 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 8/18$241
This Southwest deal was found by Cheapflights users on 8/18. 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 10/1811:20 amMDW - PWM
Nonstop2h 10mSouthwest
Wed 10/227:40 amPWM - MDW
1 stop5h 20mSouthwest
Deal found 8/18$241
This American Airlines deal was found by Cheapflights users on 8/18. 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
Wed 10/227:00 amPWM - ORD
1 stop9h 58mAmerican Airlines
Deal found 8/18$243
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/128:30 pmORD - PWM
Nonstop2h 29mAmerican Airlines
Tue 9/166:01 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 8/19$245
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sun 10/191:30 pmMDW - PWM
Nonstop2h 10mSouthwest
Sat 10/254:45 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 8/17$245
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Thu 9/46:25 pmORD - PWM
Nonstop2h 34mUnited Airlines
Sat 9/66:00 amPWM - ORD
1 stop7h 57mUnited Airlines
Deal found 8/19$246
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/310:05 amORD - PWM
1 stop9h 06mAmerican Airlines
Tue 9/96:01 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 8/18$247
This JetBlue deal was found by Cheapflights users on 8/20. 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.
Fri 9/121:35 pmORD - PWM
1 stop7h 32mJetBlue
Mon 9/152:17 pmPWM - ORD
1 stop7h 32mJetBlue
Deal found 8/20$248
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/113:32 pmORD - PWM
1 stop4h 49mAmerican Airlines
Sat 10/185:46 amPWM - ORD
1 stop6h 20mAmerican Airlines
Deal found 8/18$251
This Delta deal was found by Cheapflights users on 8/18. 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 12/179:30 amMDW - PWM
1 stop5h 40mDelta
Sat 1/1012:50 pmPWM - MDW
1 stop6h 44mDelta
Deal found 8/18$251

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 August 20, 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

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

10:05 am-8:11 pm

1 stop9h 06m

Portland

Sat 9/6

8:40 am-7:01 pm

1 stop11h 21m

$238

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 10/31

7:58 am-11:28 am

Nonstop2h 30m

Portland

Sun 11/2

5:41 am-10:58 am

1 stop6h 17m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

4:05 pm-11:20 pm

1 stop6h 15m

Portland

Wed 10/22

4:57 pm-6:48 pm

Nonstop2h 51m

$241

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 10/18

11:20 am-2:30 pm

Nonstop2h 10m

Portland

Wed 10/22

1:55 pm-6:30 pm

1 stop5h 35m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/16

9:55 am-3:15 pm

1 stop4h 20m

Portland

Tue 9/23

6:01 am-7:57 am

Nonstop2h 56m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 9/13

7:10 pm-10:43 pm

Nonstop2h 33m

Portland

Tue 9/16

6:00 am-11:06 am

1 stop6h 06m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 10/21

7:58 am-11:28 am

Nonstop2h 30m

Portland

Sat 10/25

12:34 pm-5:13 pm

1 stop5h 39m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/17

6:00 am-12:31 pm

1 stop5h 31m

Portland

Wed 9/24

6:15 am-8:11 am

Nonstop2h 56m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

7:10 pm-10:45 pm

Nonstop2h 35m

Portland

Sat 10/25

8:50 am-1:52 pm

1 stop6h 02m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

6:45 am-5:38 pm

1 stop9h 53m

Portland

Wed 10/22

7:00 am-3:58 pm

1 stop9h 58m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 26 results
1
2
3

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 8, 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 August 20, 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 morning tend to be the most expensive. A flight in the evening could potentially save you up to 19% 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 August 17, 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. Friday 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 August 20, 2025.

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

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 August 20, 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
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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.
JetBlue
7.2
Good
2,916 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Boarding

8.1

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 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 American Airlines, United Airlines, or Southwest 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 Southwest and United Airlines. Delta is 55% 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 (83%), Air New Zealand (65%) or American Airlines (63%) 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 $447, our data indicates the cheapest price to be $99. The most popular route (Chicago O'Hare Intl - Portland), is priced around $183.

  • 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$230Average$344FlexibilityNo cancel feeOn-time71%

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