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Portland

$90+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheap flight deals from Illinois to Portland

Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(Delta)

One-way from

$90
(United Airlines)

Popular in

December

Cheapest in

February

Average price

$425

Good round-trip deal

$297 or less

Good one-way deal

$129 or less
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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From Illinois to Portland
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One-way flight from Illinois to Portland
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Illinois to Portland.
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Price to beat on a one-way flight from Illinois to Portland.
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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 April 3, 2025.

This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/221:16 pmORD - PWM
2 stops9h 15mDelta
Sat 10/2512:30 pmPWM - ORD
2 stops9h 06mDelta
Deal found 4/2$239
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:56 pmORD - PWM
1 stop5h 03mUnited Airlines
Thu 5/296:00 amPWM - ORD
Nonstop2h 53mUnited Airlines
Deal found 4/2$245
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:00 amMDW - PWM
1 stop5h 35mDelta
Wed 5/285:30 amPWM - MDW
1 stop7h 23mDelta
Deal found 4/2$248
This JetBlue deal was found by Cheapflights users on 4/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/21:13 pmORD - PWM
1 stop7h 44mJetBlue
Sat 5/32:15 pmPWM - ORD
1 stop9h 07mJetBlue
Deal found 4/1$250
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 8/297:12 pmORD - PWM
Nonstop2h 34mAmerican Airlines
Sat 9/66:00 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/1$258
This Southwest deal was found by Cheapflights users on 4/1. 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.
Thu 6/122:50 pmMDW - PWM
1 stop8h 15mSouthwest
Fri 6/137:40 pmPWM - MDW
Nonstop2h 35mSouthwest
Deal found 4/1$260
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/54:30 pmMLI - PWM
1 stop5h 07mAmerican Airlines
Fri 9/125:18 pmPWM - MLI
1 stop5h 18mAmerican Airlines
Deal found 4/2$294
This Booking.com deal was found by Cheapflights users on 4/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/274:30 pmORD - PWM
1 stop25h 41mFrontier
Thu 5/19:29 pmPWM - ORD
1 stop27h 03mFrontier
Deal found 4/2$298
This Frontier deal was found by Cheapflights users on 4/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/188:56 amMDW - PWM
1 stop8h 24mFrontier
Sat 4/1910:12 amPWM - MDW
1 stop10h 35mFrontier
Deal found 4/2$298
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 7/111:50 pmORD - PWM
1 stop9h 15mSouthwest
Thu 7/245:40 amPWM - ORD
1 stop8h 25mSouthwest
Deal found 4/1$310
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:00 amSTL - PWM
1 stop4h 50mDelta
Sat 6/215:30 pmPWM - STL
1 stop7h 12mDelta
Deal found 4/2$317
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:29 amSTL - PWM
1 stop4h 41mAmerican Airlines
Fri 9/265:56 amPWM - STL
1 stop4h 57mAmerican Airlines
Deal found 4/2$336

Cheapflights Fare Finder

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 April 3, 2025.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.

Fly from

Illinois

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 6/4

1:45 pm-11:21 pm

2 stops8h 36m

Portland

Mon 6/9

11:44 am-7:19 pm

1 stop8h 35m

$244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/24

5:56 pm-11:59 pm

1 stop5h 03m

Portland

Thu 5/29

6:00 am-7:53 am

Nonstop2h 53m

$245

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 5/21

6:00 am-12:35 pm

1 stop5h 35m

Portland

Wed 5/28

5:30 am-11:53 am

1 stop7h 23m

$248

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/2

1:13 pm-9:57 pm

1 stop7h 44m

Portland

Sat 5/3

2:15 pm-10:22 pm

1 stop9h 07m

$250

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/12

2:50 pm-12:05 am

1 stop8h 15m

Portland

Fri 6/13

7:40 pm-9:15 pm

Nonstop2h 35m

$260

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 6/11

5:50 pm-11:59 pm

1 stop5h 09m

Portland

Sun 6/15

6:00 am-7:57 am

Nonstop2h 57m

$268

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

Fri 9/5

4:30 pm-10:37 pm

1 stop5h 07m

Portland

Fri 9/12

5:18 pm-9:36 pm

1 stop5h 18m

$294

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 4/27

4:30 pm-7:11 pm

1 stop25h 41m

Portland

Thu 5/1

9:29 pm-11:32 pm

1 stop27h 03m

$298

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 4/18

8:56 am-6:20 pm

1 stop8h 24m

Portland

Sat 4/19

10:12 am-7:47 pm

1 stop10h 35m

$298

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Tue 6/17

6:00 am-1:13 pm

1 stop6h 13m

Portland

Tue 6/24

6:56 pm-11:42 pm

1 stop5h 46m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 37 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Portland

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 May is currently the most expensive (average of $416). 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 April 3, 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 April 3, 2025.

The most flights from USIL to PWM are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, 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 April 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United 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
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,619 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 United Airlines. According to our data, you can fly for as low as $90. Users have also found prices from $102 and $106 on JetBlue and Frontier, 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: SkyWest Airlines (85%), Air New Zealand (85%), United Airlines( 76%).

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

    The cheapest flight price from Illinois to Portland, Maine is $89. On average you can expect to pay $285. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $183.

  • 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 May is currently the most expensive (average of $416). 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
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Alternative routes for Illinois 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 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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$89FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$433FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
DeltaCheapest$217Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$408FlexibilityNo cancel feeOn-time69%

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