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Portland

$119+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Portland are usually found in February or March, booked 64 days in advance, depart on a Tuesday or Sunday 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 julio 3, 2025.

Round-trip from

$237
(JetBlue)

One-way from

$119
(JetBlue)

Popular in

December

Cheapest in

February

Average price

$347

Good round-trip deal

$245 or less

Good one-way deal

$129 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. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 3, 2025.

This JetBlue deal was found by Cheapflights users on 7/2. 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.
jue. 8/146:15 amORD - PWM
1 stop6h 08mJetBlue
sáb. 8/236:05 amPWM - ORD
1 stop6h 13mJetBlue
Deal found 7/2$237
This Delta deal was found by Cheapflights users on 7/1. 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.
mar. 8/125:45 amORD - PWM
2 stops9h 25mDelta
vie. 10/315:59 pmPWM - ORD
1 stop5h 38mDelta
Deal found 7/1$239
This Delta deal was found by Cheapflights users on 7/1. 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.
mar. 8/1212:43 pmMDW - PWM
2 stops9h 42mDelta
vie. 10/3112:50 pmPWM - MDW
1 stop6h 46mDelta
Deal found 7/1$239
This United Airlines deal was found by Cheapflights users on 6/30. 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.
mar. 8/123:40 pmORD - PWM
1 stop6h 34mUnited Airlines
sáb. 8/306:14 amPWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 6/30$241
This Southwest deal was found by Cheapflights users on 7/1. 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.
mar. 8/1211:40 amMDW - PWM
Nonstop2h 15mSouthwest
sáb. 8/305:45 amPWM - MDW
1 stop6h 25mSouthwest
Deal found 7/1$241
This American Airlines deal was found by Cheapflights users on 7/1. 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.
vie. 9/198:30 pmORD - PWM
Nonstop2h 29mAmerican Airlines
mar. 9/236:00 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 7/1$245
This Southwest deal was found by Cheapflights users on 7/2. 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.
sáb. 10/2512:40 pmORD - PWM
1 stop6h 25mSouthwest
jue. 10/309:15 amPWM - ORD
1 stop4h 30mSouthwest
Deal found 7/2$274
This Orbitz deal was found by Cheapflights users on 7/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/29:08 amORD - PWM
1 stop8h 05mFrontier
sáb. 8/96:58 pmPWM - ORD
2 stops16h 27mFrontier
Deal found 7/3$300
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/129:08 amORD - PWM
1 stop8h 05mMultiple Airlines
lun. 7/1412:46 pmPWM - ORD
1 stop5h 35mMultiple Airlines
Deal found 7/1$304

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 julio 3, 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

jue. 8/14

6:15 am-1:23 pm

1 stop6h 08m

Portland

sáb. 8/23

6:05 am-11:18 am

1 stop6h 13m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 8/12

5:45 am-4:10 pm

2 stops9h 25m

Portland

vie. 10/31

5:59 pm-10:37 pm

1 stop5h 38m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mar. 8/12

12:43 pm-11:25 pm

2 stops9h 42m

Portland

vie. 10/31

12:50 pm-6:36 pm

1 stop6h 46m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 8/12

3:40 pm-11:14 pm

1 stop6h 34m

Portland

sáb. 8/30

6:14 am-8:05 am

Nonstop2h 51m

$241

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mar. 8/12

11:40 am-2:55 pm

Nonstop2h 15m

Portland

sáb. 8/30

5:45 am-11:10 am

1 stop6h 25m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 9/19

8:30 pm-11:59 pm

Nonstop2h 29m

Portland

mar. 9/23

6:00 am-7:56 am

Nonstop2h 56m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 9/3

1:50 pm-10:25 pm

1 stop7h 35m

Portland

sáb. 9/6

1:15 pm-10:00 pm

2 stops9h 45m

$284

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 8/2

9:08 am-6:13 pm

1 stop8h 05m

Portland

sáb. 8/9

6:58 pm-10:25 am

2 stops16h 27m

$300

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 7/12

9:08 am-6:13 pm

1 stop8h 05m

Portland

lun. 7/14

12:46 pm-5:21 pm

1 stop5h 35m

$304

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

dom. 8/17

6:15 am-1:23 pm

1 stop6h 08m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 20 results
1
2

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 June 27, 2025.

The best time to book flights from Chicago to Portland, Maine is 64 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 julio 3, 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 June 29, 2025.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday at noon when fares are most often at their lowest. Friday mornings 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 julio 3, 2025.

The most flights from CHI to PWM are scheduled on a Thursday (11 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 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 julio 3, 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
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 6 inbound flights from Chicago per day from 5 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

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

    JetBlue, at $237, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Delta and United Airlines. JetBlue is 32% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Portland, Maine one-way?

    One-way options have recently been found by users for as low as $119 on JetBlue. Other airlines that offer cheap prices include Delta from $126 and Frontier from $128 one-way.

  • 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 SkyWest Airlines (94%), American Airlines (88%) or Envoy Air (85%) 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 $283, our data indicates the cheapest price to be $89. 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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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 5 airlines flying from Chicago to Portland

Discover the top 5 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$89FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$187Average$345FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$401FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$213Average$387FlexibilityNo cancel feeOn-time69%

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