HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$55+ Cheap flights from Illinois 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Portland 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.

Cheap flight deals from Illinois to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) 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 January 21, 2025.

Round-trip from

$159
(Mytrip)

One-way from

$55
(Frontier)

Good round-trip deal

$279 or less

Good one-way deal

$258 or less
From Illinois to Portland
Search Deals
One-way flight from Illinois to Portland
Search Deals
Price to beat on a round-trip flight from Illinois to Portland.
Search Deals
Price to beat on a one-way flight from Illinois to Portland.
Search Deals

Find flight deals from Illinois to Portland

Cheapest flights from Illinois to Portland
Explore the most affordable flight options available from Illinois to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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.
Sat 3/110:20 amORD - PWM
1 stop21h 58mFrontier
Mon 3/38:35 pmPWM - ORD
1 stop17h 45mFrontier
Deal found 1/21$159
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:20 amORD - PWM
1 stop6h 00mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 1/20$185
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Wed 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Deal found 1/20$209
This KAYAK deal was found by Cheapflights users on 1/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/177:05 amORD - PWM
1 stop6h 17mDelta
Thu 2/206:00 amPWM - ORD
1 stop5h 49mDelta
Deal found 1/21$214
This Delta deal was found by Cheapflights users on 1/21. 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 3/256:42 pmMDW - PWM
1 stop3h 32mDelta
Sat 3/297:00 amPWM - MDW
1 stop6h 32mDelta
Deal found 1/21$223
This Southwest deal was found by Cheapflights users on 1/21. 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 4/84:20 pmMDW - PWM
1 stop5h 10mSouthwest
Tue 4/152:20 pmPWM - MDW
1 stop8h 30mSouthwest
Deal found 1/21$237
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 pmORD - PWM
Nonstop2h 27mUnited Airlines
Sun 11/25:00 amPWM - ORD
1 stop5h 47mUnited Airlines
Deal found 1/20$252
This Frontier deal was found by Cheapflights users on 1/21. 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 2/65:05 pmSTL - PWM
1 stop26h 07mFrontier
Mon 2/109:02 pmPWM - STL
1 stop27h 29mFrontier
Deal found 1/21$273
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/315:30 amMDW - PWM
1 stop12h 18mFrontier
Sun 2/27:06 pmPWM - MDW
1 stop16h 22mFrontier
Deal found 1/20$280
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/15:15 amORD - PWM
2 stops13h 12mMultiple Airlines
Mon 3/36:18 pmPWM - ORD
2 stops28h 45mMultiple Airlines
Deal found 1/20$297
This Southwest deal was found by Cheapflights users on 1/21. 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.
Fri 2/287:00 amORD - PWM
2 stops8h 35mSouthwest
Tue 3/45:35 amPWM - ORD
1 stop9h 25mSouthwest
Deal found 1/21$309
This Mytrip deal was found by Cheapflights users on 1/21. 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 2/64:28 pmSTL - PWM
2 stops23h 42mMultiple Airlines
Mon 2/106:18 pmPWM - STL
2 stops21h 25mMultiple Airlines
Deal found 1/21$319

Find flights from Illinois to Portland within your budget

Customize your flight search to find flights from Illinois 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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2/28

5:10 am-7:35 pm

1 stop13h 25m

Portland

Tue 3/4

10:08 am-10:38 pm

1 stop13h 30m

$160

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 2/16

12:54 pm-4:12 pm

Nonstop2h 18m

Portland

Sat 2/22

4:04 pm-6:10 pm

Nonstop3h 06m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 2/17

7:05 am-2:22 pm

1 stop6h 17m

Portland

Thu 2/20

6:00 am-10:49 am

1 stop5h 49m

$214

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 2/18

1:54 pm-10:25 pm

1 stop7h 31m

Portland

Tue 2/25

2:29 pm-7:23 pm

1 stop5h 54m

$217

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 3/25

6:42 pm-11:14 pm

1 stop3h 32m

Portland

Sat 3/29

7:00 am-12:32 pm

1 stop6h 32m

$223

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 4/8

4:20 pm-10:30 pm

1 stop5h 10m

Portland

Tue 4/15

2:20 pm-9:50 pm

1 stop8h 30m

$237

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Thu 2/6

5:05 pm-8:12 pm

1 stop26h 07m

Portland

Mon 2/10

9:02 pm-11:31 pm

1 stop27h 29m

$273

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 1/31

5:30 am-6:48 pm

1 stop12h 18m

Portland

Sun 2/2

7:06 pm-10:28 am

1 stop16h 22m

$280

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

5:15 am-7:27 pm

2 stops13h 12m

Portland

Mon 3/3

6:18 pm-10:40 am

3 stops17h 22m

$292

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2/28

7:00 am-4:35 pm

2 stops8h 35m

Portland

Tue 3/4

5:35 am-2:00 pm

1 stop9h 25m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 38 results
1
2
3
4

Best time to book a flight from Illinois to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Illinois 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 Illinois to Portland

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

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $296). Flying from Illinois to Portland, Maine in April is currently the most expensive (average of $498). 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 IL to PWM?

Find hourly flight availability from Illinois 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 January 21, 2025.

When flying from Illinois to Portland, Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Illinois to Portland, Maine

Explore weekly flight availability from Illinois 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 January 21, 2025.

The most flights from USIL to PWM are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 January 21, 2025.
Peruse reviews from past customers who have flown with Delta, Southwest and American Airlines from Illinois to Portland to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois?

    For a flight from Illinois to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $87 and $109 on JetBlue and Delta, respectively.

  • What are the most popular routes from Illinois to Portland, Maine?

    The most popular flight routes from Illinois to Portland, Maine are Chicago O'Hare Intl - Portland, Chicago Midway - Portland and Lambert-St Louis - Portland.

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

    Before booking your flight to Portland, Maine from Illinois, check out the most reliable airlines to get you to your destination on time: Republic Airways (86%), United Airlines (85%), Air New Zealand( 85%).

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

    The cheapest flight price from Illinois to Portland, Maine is $218. On average you can expect to pay $314. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $177.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $296). Flying from Illinois to Portland, Maine in April is currently the most expensive (average of $498). 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 Illinois?

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

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.

Alternative routes for Illinois to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Los Angeles to Boston flights
Dallas/Fort Worth to Boston flights
Reagan-National to Boston flights
San Francisco to Boston flights
Fort Lauderdale to Boston flights
Dulles Intl to Boston flights
Seattle to Boston flights
Orlando to Boston flights
Hobby to Boston flights
Baltimore to Boston flights
Philadelphia to Boston flights
Newark to Boston flights
Minneapolis to Boston flights
Miami to Boston flights
Denver to Boston flights
LaGuardia to Boston flights
Atlanta to Boston flights
George Bush Intcntl to Boston flights
Austin to Boston flights
Raleigh to Boston flights
Charlotte to Boston flights
Cincinnati to Boston flights
John F Kennedy Intl to Boston flights
Tampa to Boston flights
Cleveland to Boston flights
Ontario to Boston flights
Indianapolis to Boston flights
Pittsburgh to Boston flights
Sky Harbor Intl to Boston flights
Detroit to Boston flights
West Palm Beach to Boston flights
Columbus to Boston flights
Nashville to Boston flights
Portland to Boston flights
San Diego to Boston flights
Milwaukee to Boston flights
Salt Lake City to Boston flights
Jacksonville to Boston flights
Richmond to Boston flights
Newark to Portland flights
Midway to Boston flights
Burbank to Boston flights
Love Field to Boston flights
Louisville to Boston flights
Kansas City to Boston flights
San Antonio to Boston flights
Las Vegas to Boston flights
Dulles Intl to Portland flights
St. Louis to Boston flights

Top 5 airlines flying from Illinois to Portland

Discover the top 5 airlines that operate flights from Illinois 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$181Average$441FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$330FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$222Average$416FlexibilityNo cancel feeOn-time69%
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.