HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$60+ Cheap flights from Portland (PWM) to Chicago (CHI)

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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
We work with more than 300 partners to bring you better travel deals

...and more

Find cheap flights from Portland to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Portland to Chicago are usually found in September or August, booked 39 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to Chicago

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

April

Cheapest in

September

Round-trip from

$158
(CheapOair)

One-way from

$60
(Frontier)
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
High demand for flights, 34% potential price rise
Search Deals
Best time to find cheap flights, 25% potential price drop
Search Deals
From Portland to Chicago (CHI)
Search Deals
One-way flight from Portland to Chicago (CHI)
Search Deals

Find flight deals from Portland to Chicago

Cheapest flights from Portland to Chicago
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2024.

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.
Fri 12/66:14 pmPWM - ORD
2 stops16h 24mMultiple Airlines
Sun 12/87:45 pmORD - PWM
1 stop14h 36mMultiple Airlines
Deal found 11/13$266
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/65:50 amPWM - ORD
1 stop6h 07mAmerican Airlines
Sun 12/86:30 amORD - PWM
1 stop4h 35mAmerican Airlines
Deal found 11/14$267
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/248:15 pmPWM - MDW
1 stop12h 40mFrontier
Tue 11/268:50 amMDW - PWM
1 stop9h 25mFrontier
Deal found 11/13$268
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:00 amPWM - ORD
1 stop6h 38mUnited Airlines
Sat 1/46:10 pmORD - PWM
Nonstop2h 32mUnited Airlines
Deal found 11/14$289
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.
Mon 12/166:05 amPWM - MDW
1 stop6h 53mDelta
Thu 12/1911:48 amMDW - PWM
2 stops11h 22mDelta
Deal found 11/14$298
This Delta deal was found by Cheapflights users on 11/12. 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 12/132:55 pmPWM - ORD
1 stop8h 01mDelta
Tue 12/1712:25 pmORD - PWM
2 stops9h 52mDelta
Deal found 11/12$303
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/161:15 pmPWM - MDW
2 stops10h 05mSouthwest
Thu 12/193:00 pmMDW - PWM
2 stops7h 55mSouthwest
Deal found 11/14$318
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.
Wed 12/116:00 amPWM - ORD
1 stop9h 00mSouthwest
Sun 12/151:45 pmORD - PWM
2 stops9h 10mSouthwest
Deal found 11/13$362
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/155:54 pmPWM - ORD
1 stop24h 47mFrontier
Sun 11/175:05 amORD - PWM
1 stop13h 07mFrontier
Deal found 11/13$398
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/164:30 pmPWM - MDW
3 stops22h 01mWestJet
Thu 12/1911:48 amMDW - PWM
3 stops23h 01mWestJet
Deal found 11/14$1,596

Find flights from Portland to Chicago within your budget

Customize your flight search to find flights from Portland to Chicago 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

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/24

12:15 pm-5:21 pm

1 stop6h 06m

Chicago O'Hare Intl

Sun 4/27

6:00 am-11:21 am

1 stop4h 21m

$263

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sun 11/24

8:15 pm-7:55 am

1 stop12h 40m

Chicago Midway

Tue 11/26

8:50 am-7:15 pm

1 stop9h 25m

$268

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/9

6:00 am-10:47 am

1 stop5h 47m

Chicago O'Hare Intl

Sun 4/13

6:00 pm-9:27 pm

Nonstop2h 27m

$273

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 12/16

5:56 pm-4:06 pm

2 stops23h 10m

Chicago O'Hare Intl

Thu 12/19

6:05 am-4:35 pm

1 stop9h 30m

$277

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 2/16

5:59 pm-10:46 pm

1 stop5h 47m

Chicago O'Hare Intl

Wed 2/19

7:30 am-1:59 pm

1 stop5h 29m

$293

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 12/16

6:05 am-11:58 am

1 stop6h 53m

Chicago Midway

Thu 12/19

11:48 am-12:10 am

2 stops11h 22m

$298

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 12/13

6:10 pm-10:00 pm

1 stop4h 50m

Chicago Midway

Tue 12/17

10:05 am-3:15 pm

1 stop4h 10m

$343

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 12/13

5:30 am-3:00 pm

2 stops10h 30m

Chicago O'Hare Intl

Wed 12/18

11:25 am-10:30 pm

2 stops10h 05m

$362

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/23

6:10 am-10:16 am

1 stop5h 06m

Chicago O'Hare Intl

Sun 4/27

11:01 am-4:35 pm

1 stop4h 34m

$382

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 12/6

12:01 pm-6:32 pm

3 stops31h 31m

Chicago Midway

Sun 12/8

9:38 am-11:49 am

3 stops25h 11m

$1,295

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 23 results
1
2
3

Compare providers for flights from Portland to Chicago

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

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on November 8, 2024.

Booking 39 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $232). Flying from Portland, Maine to Chicago 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 CHI?

Find hourly flight availability from Portland to Chicago. 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 Portland, Maine to Chicago 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 68% on airfare.

Weekly flight availability from Portland, Maine to Chicago

Explore weekly flight availability from Portland to Chicago. 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 PWM to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago 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 when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 14, 2024.
Get a feel of what it's like to fly with Southwest, Frontier and American Airlines from Portland to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,045 reviews

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

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

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

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

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

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

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

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

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,045 reviews

Boarding

8.3

Food

7.2

Comfort

8.1

Crew

8.7

Overall

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 Portland to Chicago. 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?

    For a flight from Portland to Chicago, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 4 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Portland on a regular basis.

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

    Cheapflights users have booked flights from Portland, Maine to Chicago round-trip from $158. Other airlines that can offer you cheap pricing are American Airlines, from $178, and United Airlines, from $209. These flights start at 59% lower than the current average price 3 months from now.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $60. Users have also found prices from $84 and $114 on American Airlines and Delta, respectively.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Chicago on time: Qatar Airways (96%), American Airlines (92%), Envoy Air (92%).

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

    On average you can expect to pay $953 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $182 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $183.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $232). Flying from Portland, Maine to Chicago 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 5 airlines flying from Portland to Chicago

Discover the top 5 airlines that operate flights from Portland to Chicago. 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$112FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$360FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$350FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$411FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$387FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines