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$70+ Cheap flights from Portland (PWM) to O'Hare Intl (ORD)

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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Oct 15 — Oct 221
From?
To?
Tue 10/15
Tue 10/22
1 adult, Economy
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The best prices from Portland to Chicago O'Hare Intl are usually found in September or August, booked 57 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to O'Hare Intl (ORD). 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 October 10, 2024.

Popular in

April

Cheapest in

September

Round-trip from

$138
(Frontier)

One-way from

$70
(Frontier)
High demand for flights, 31% potential price rise
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Best time to find cheap flights, 27% potential price drop
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From Portland to Chicago O'Hare Intl
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One-way flight from Portland to Chicago O'Hare Intl
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Cheap Portland to O'Hare Intl flights in October & November 2024

Find cheap flight options from Portland to O'Hare Intl specifically for the months of October and November 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Prices were last updated on October 10, 2024.
Listed are some of the best fares we've found on flights departing from Portland to Chicago in 2024. Check back regularly for other flight deals.
This Mytrip deal was found by Cheapflights users on 10/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/85:54 pmPWM - ORD
1 stop24h 47mFrontier
Sun 11/105:05 amORD - PWM
1 stop12h 49mFrontier
Deal found 10/10$151
This Booking.com deal was found by Cheapflights users on 10/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2412:31 pmPWM - ORD
1 stop6h 54mMultiple Airlines
Sun 10/275:10 amORD - PWM
1 stop12h 35mMultiple Airlines
Deal found 10/10$254
This United Airlines deal was found by Cheapflights users on 10/10. 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 11/64:30 pmPWM - ORD
Nonstop3h 12mUnited Airlines
Wed 11/1311:05 amORD - PWM
Nonstop2h 30mUnited Airlines
Deal found 10/10$317
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/111:23 amPWM - ORD
1 stop9h 19mAmerican Airlines
Sat 11/25:20 pmORD - PWM
1 stop17h 34mAmerican Airlines
Deal found 10/10$323
This Southwest deal was found by Cheapflights users on 10/10. 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.
Wed 11/66:00 amPWM - ORD
2 stops13h 10mSouthwest
Wed 11/135:45 amORD - PWM
1 stop5h 50mSouthwest
Deal found 10/10$341
This Delta deal was found by Cheapflights users on 10/10. 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 11/16:35 amPWM - ORD
1 stop14h 40mDelta
Wed 11/62:45 pmORD - PWM
1 stop7h 34mDelta
Deal found 10/10$345

Portland to O'Hare Intl 2024 flight deals

Discover exclusive flight deals for travel between Portland and O'Hare Intl in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
Listed are some of the best fares we've found on flights departing from Portland to Chicago in 2024. Check back regularly for other flight deals.
This Booking.com deal was found by Cheapflights users on 10/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:13 pmPWM - ORD
1 stop12h 11mFrontier
Sun 12/89:35 amORD - PWM
1 stop9h 39mFrontier
Deal found 10/10$148
This Booking.com deal was found by Cheapflights users on 10/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2412:31 pmPWM - ORD
1 stop6h 54mMultiple Airlines
Sun 10/275:10 amORD - PWM
1 stop12h 35mMultiple Airlines
Deal found 10/10$254
This United Airlines deal was found by Cheapflights users on 10/10. 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 11/64:30 pmPWM - ORD
Nonstop3h 12mUnited Airlines
Wed 11/1311:05 amORD - PWM
Nonstop2h 30mUnited Airlines
Deal found 10/10$317
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/111:23 amPWM - ORD
1 stop9h 19mAmerican Airlines
Sat 11/25:20 pmORD - PWM
1 stop17h 34mAmerican Airlines
Deal found 10/10$323
This Southwest deal was found by Cheapflights users on 10/10. 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.
Wed 11/66:00 amPWM - ORD
2 stops13h 10mSouthwest
Wed 11/135:45 amORD - PWM
1 stop5h 50mSouthwest
Deal found 10/10$341
This Delta deal was found by Cheapflights users on 10/10. 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 11/16:35 amPWM - ORD
1 stop14h 40mDelta
Wed 11/62:45 pmORD - PWM
1 stop7h 34mDelta
Deal found 10/10$345

Portland to O'Hare Intl flights leaving soon

Find last-minute flight options from Portland to O'Hare Intl for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
Have a look at some of the last-minute flights available departing from Portland to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/166:15 amPWM - ORD
Nonstop2h 46mUnited Airlines
Fri 10/183:35 pmORD - PWM
1 stop7h 24mUnited Airlines
Deal found 10/9$359
This Delta deal was found by Cheapflights users on 10/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/165:02 amPWM - ORD
1 stop5h 52mDelta
Fri 10/181:40 pmORD - PWM
1 stop7h 15mDelta
Deal found 10/9$368
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Thu 10/176:01 amPWM - ORD
1 stop7h 20mAmerican Airlines
Tue 10/227:40 pmORD - PWM
Nonstop2h 28mAmerican Airlines
Deal found 10/10$369

One-way flights to O'Hare Intl from Portland

Search for one-way flight options from Portland to O'Hare Intl. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
Some of the best available deals we've found on one-way flights from Portland to Chicago. Those needing a return flight from Portland to Chicago can use the search form above.
This Frontier deal was found by Cheapflights users on 10/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/271:22 pmPWM - ORD
1 stop11h 45mFrontier
Deal found 10/9$70
This JetBlue deal was found by Cheapflights users on 10/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/86:10 amPWM - ORD
1 stop5h 06mJetBlue
Deal found 10/9$103
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Tue 1/74:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 10/10$123
This Delta deal was found by Cheapflights users on 10/10. 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.
Tue 1/74:40 pmPWM - ORD
1 stop5h 33mDelta
Deal found 10/10$132
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2912:25 pmPWM - ORD
Nonstop2h 53mAmerican Airlines
Deal found 10/9$180
This Southwest deal was found by Cheapflights users on 10/10. 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.
Mon 12/96:00 amPWM - ORD
2 stops8h 00mSouthwest
Deal found 10/10$193
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1712:31 pmPWM - ORD
3 stops21h 32mMultiple Airlines
Deal found 10/9$464

Find flights from Portland to O'Hare Intl within your budget

Customize your flight search to find flights from Portland to O'Hare Intl 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 2,713,696 searches. Data last updated October 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$138 - $383

Route

Depart

Return

Price

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 12/5

1 stop12h 11m

Chicago O'Hare Intl

Sun 12/8

1 stop9h 39m

$138

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 10/24

1 stop6h 54m

Chicago O'Hare Intl

Sun 10/27

1 stop12h 35m

$252

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Sat 1/18

1 stop5h 10m

Chicago O'Hare Intl

Tue 1/21

1 stop5h 29m

$264

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Sat 1/18

Nonstop3h 14m

Chicago O'Hare Intl

Tue 1/21

Nonstop2h 32m

$305

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Fri 11/1

1 stop9h 19m

Chicago O'Hare Intl

Tue 11/5

1 stop5h 21m

$345

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Fri 12/6

1 stop9h 00m

Chicago O'Hare Intl

Sun 12/8

2 stops9h 10m

$383

Flights are sorted by cheapest first

Deals found on 10/10

Best time to book a flight from Portland to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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.

Travel insights for flights from Portland to O'Hare Intl

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

How far ahead should I book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Portland to O'Hare Intl. Price data was last updated on October 4, 2024.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Chicago O'Hare Intl Airport, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Find deals

What is the cheapest month to book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $232). Flying from Portland, Maine to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $308). 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 ORD?

Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 10, 2024.

Unlike in the morning, when flights are generally more expensive, you can save up to 67% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets in the evening.

Weekly flight availability from Portland, Maine to Chicago O'Hare Intl Airport

Explore weekly flight availability from Portland to O'Hare Intl. 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 October 10, 2024.

The most flights from PWM to ORD are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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 73.4 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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated October 10, 2024.
See what other customers who have flown with Delta, United Airlines and American 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
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

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

Southwest
8.2
Very good
5,203 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,963 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

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

JetBlue
7.5
Good
3,593 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,366 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

Reviews

1 / 10

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

American Airlines
7.3
Good
10,000 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Overall

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Boarding

8.3

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 Portland to O'Hare Intl. 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 O'Hare Intl?

    Most people fly from Portland (PWM) if they book a flight from Portland to Chicago O'Hare Intl. On average, Portland has 9 outbound flights to Chicago O'Hare Intl per day from 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • Can I find flights from Portland, Maine to Chicago O'Hare Intl Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from Portland, Maine to Chicago O'Hare Intl Airport for under $200. The cheapest flight booked recently is on Frontier for just $138, but on average you can expect to pay $281.

  • Are there nonstop flights from Portland, Maine to Chicago O'Hare Intl Airport for under $400 on Cheapflights?

    Cheapflights has at least 2 direct flights from Portland, Maine to Chicago O'Hare Intl Airport under $400. A good price for a nonstop flight from Portland, Maine to Chicago O'Hare Intl Airport is less than $339.

  • Are there last-minute flights available from Portland, Maine to Chicago O'Hare Intl Airport for under $400?

    There are currently 3+ open flights from Portland, Maine to Chicago O'Hare Intl Airport within the next 7 days for less than $400.

  • What are the cheapest airlines flying from Portland, Maine to Chicago O'Hare Intl Airport round-trip?

    According to our current data, Frontier ($138), Delta ($264), and United Airlines ($305) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 65% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Portland, Maine to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $70. JetBlue flights start at $103 while deals on United Airlines start at $123 one-way.

  • What are the most reliable airlines from Portland, Maine to Chicago O'Hare Intl Airport?

    Consider Republic Airways (86%), Qatar Airways (80%) or Air New Zealand (77%) when booking your flight. These represent the most reliable airlines when flying from Portland, Maine to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Portland, Maine to Chicago O'Hare Intl Airport?

    Looking for the cheapest flight from Portland, Maine to Chicago O'Hare Intl Airport? While on average our users pay $901, our data indicates the cheapest price to be $156. The most popular route (Portland - Chicago O'Hare Intl), is priced around $249.

  • What does PWM to ORD mean?

    Portland Airport is PWM and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

  • Can I find deals for flights from Portland to O'Hare Intl that include extra baggage allowance?

    The amount of baggage you can bring on your Portland to O'Hare Intl flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Portland to O'Hare Intl with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to O'Hare Intl flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Portland to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Portland to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to O'Hare Intl?

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

  • Can I find deals for business class flights from Portland to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Portland to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Portland to O'Hare Intl that allow pets onboard?

    Many airlines flying from Portland to O'Hare Intl offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Portland to O'Hare Intl?

    Yes, you can often find last-minute deals on Portland to O'Hare Intl flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Portland, Maine to Chicago O'Hare Intl Airport flight deals updated?

    The Portland, Maine to Chicago O'Hare Intl Airport flight deals you see on this page were last updated on 10/10.

  • What is the cheapest month to book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $232). Flying from Portland, Maine to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $308). 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

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