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$53+ Cheap flights from Chicago (CHI) to Portland (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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Nov 19 — Nov 261
Tue 11/19
Tue 11/26
1 adult, Economy
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The best prices from Chicago to Portland are usually found in January or June, booked 89 days in advance, depart on a Tuesday or Thursday 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 November 14, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

January

Round-trip from

$118
(Frontier)

One-way from

$53
(Cheapflightsfares)
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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High demand for flights, 30% potential price rise
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Best time to find cheap flights, 27% potential price drop
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From Chicago (CHI) to Portland
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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 November 14, 2024.

This United Airlines deal was found by Cheapflights users on 11/13. 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 12/316:08 pmORD - PWM
1 stop4h 51mUnited Airlines
Sat 1/184:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 11/13$273
This Booking.com deal was found by Cheapflights users on 11/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/216:49 pmMDW - PWM
1 stop23h 02mFrontier
Mon 1/611:23 amPWM - MDW
1 stop26h 06mFrontier
Deal found 11/13$278
This American Airlines deal was found by Cheapflights users on 11/13. 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 11/269:55 amORD - PWM
1 stop4h 36mAmerican Airlines
Tue 12/35:22 amPWM - ORD
1 stop6h 36mAmerican Airlines
Deal found 11/13$282
This Frontier deal was found by Cheapflights users on 11/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1910:59 amORD - PWM
1 stop6h 50mFrontier
Sun 12/297:51 pmPWM - ORD
1 stop15h 03mFrontier
Deal found 11/13$283
This Delta deal was found by Cheapflights users on 11/13. 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 12/114:58 pmMDW - PWM
1 stop5h 32mDelta
Sun 12/156:05 amPWM - MDW
1 stop6h 53mDelta
Deal found 11/13$293
This Delta deal was found by Cheapflights users on 11/14. 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.
Sat 12/141:45 pmORD - PWM
2 stops9h 23mDelta
Mon 12/165:05 amPWM - ORD
2 stops8h 43mDelta
Deal found 11/14$303
This Mytrip deal was found by Cheapflights users on 11/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/127:45 pmORD - PWM
1 stop14h 36mMultiple Airlines
Sat 12/1412:09 pmPWM - ORD
2 stops13h 24mMultiple Airlines
Deal found 11/13$312
This Southwest deal was found by Cheapflights users on 11/13. 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.
Thu 12/1210:05 amMDW - PWM
1 stop4h 10mSouthwest
Sun 12/156:10 pmPWM - MDW
1 stop4h 50mSouthwest
Deal found 11/13$342
This Southwest deal was found by Cheapflights users on 11/13. 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 12/2411:25 amORD - PWM
2 stops10h 05mSouthwest
Mon 12/305:30 amPWM - ORD
1 stop9h 30mSouthwest
Deal found 11/13$361
This Mytrip deal was found by Cheapflights users on 11/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/119:38 amMDW - PWM
3 stops29h 57mMultiple Airlines
Sun 12/154:30 pmPWM - MDW
3 stops27h 02mMultiple Airlines
Deal found 11/13$910

Find flights from Chicago to Portland within your budget

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 1/18

11:10 am-2:42 pm

Nonstop2h 32m

Portland

Thu 1/23

4:10 pm-6:24 pm

Nonstop3h 14m

$270

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 2/27

2:45 pm-11:22 am

1 stop19h 37m

Portland

Tue 3/4

11:46 am-1:59 pm

1 stop27h 13m

$280

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 12/15

9:35 am-8:14 pm

1 stop9h 39m

Portland

Sun 12/29

7:51 pm-9:54 am

1 stop15h 03m

$283

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 12/6

4:58 pm-12:10 am

1 stop6h 12m

Portland

Wed 12/11

5:05 am-8:58 am

1 stop4h 53m

$293

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 11/29

9:55 am-3:31 pm

1 stop4h 36m

Portland

Thu 12/5

5:50 am-10:57 am

1 stop6h 07m

$297

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 1/17

10:30 am-4:06 pm

1 stop4h 36m

Portland

Wed 1/22

6:00 am-5:25 pm

2 stops12h 25m

$298

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 1/21

5:05 pm-10:15 pm

1 stop4h 10m

Portland

Sat 1/25

12:55 pm-6:25 pm

1 stop6h 30m

$308

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 12/5

7:45 pm-5:34 pm

2 stops20h 49m

Portland

Tue 12/10

11:55 am-11:11 pm

1 stop12h 16m

$313

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 12/24

11:25 am-10:30 pm

2 stops10h 05m

Portland

Mon 12/30

5:30 am-2:00 pm

1 stop9h 30m

$361

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 1/13

11:33 am-8:12 pm

1 stop7h 39m

$53

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 21 results
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Compare providers for flights from Chicago to Portland

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 Chicago to Portland in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 Chicago-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Portland, Maine 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 Chicago-Portland, Maine 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 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.

Travel insights for flights from Chicago to Portland

Get recent, data-driven insights about flights from Chicago to Portland including ideal travel times, pricing trends, and more.

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 November 8, 2024.

The best time to book flights from Chicago to Portland, Maine is 89 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 $295). Flying from Chicago to Portland, Maine in April is currently the most expensive (average of $497). 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 November 14, 2024.

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 afternoon could potentially save you up to 37% 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 November 10, 2024.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Thursday at noon 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 November 14, 2024.

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

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 November 14, 2024.
Read reviews from past customers who have flown Frontier, United Airlines and Delta from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,447 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,194 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,045 reviews

Overall

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 5 inbound flights from Chicago per day from 4 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?

    Frontier, at $118, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Frontier is 67% 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 $53 on Frontier. Other airlines that offer cheap prices include American Airlines from $89 and JetBlue from $103 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 Air New Zealand (95%), Republic Airways (92%) or United Airlines (91%) 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 $397, our data indicates the cheapest price to be $186. The most popular route (Chicago O'Hare Intl - Portland), is priced around $203.

  • 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 $295). Flying from Chicago to Portland, Maine in April is currently the most expensive (average of $497). 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.

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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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$184Average$343FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$316FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$401FlexibilityNo cancel feeOn-time69%
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