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Illinois

$90+ Cheap flights from Portland, ME (PWM) to Illinois

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
abr. 7 — abr. 141
lun. 4/7
lun. 4/14
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated abril 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Booking.com)

One-way from

$90
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$389

Good round-trip deal

$376 or less

Good one-way deal

$195 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Portland to Illinois
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One-way flight from Portland to Illinois
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Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 Portland to Illinois.
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Price to beat on a one-way flight from Portland to Illinois.
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Find flight deals from Portland to Illinois

Cheapest flights from Portland to Illinois
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 2, 2025.

This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/129:30 pmPWM - STL
1 stop27h 36mFrontier
jue. 5/155:45 pmSTL - PWM
1 stop25h 55mFrontier
Deal found 4/1$208
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/66:13 amPWM - ORD
Nonstop2h 52mUnited Airlines
mar. 5/135:55 pmORD - PWM
1 stop5h 04mUnited Airlines
Deal found 4/1$219
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.
lun. 5/123:35 pmPWM - ORD
1 stop7h 19mJetBlue
mar. 5/136:15 amORD - PWM
1 stop7h 25mJetBlue
Deal found 4/1$225
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.
vie. 5/24:40 pmPWM - MDW
1 stop4h 25mSouthwest
dom. 5/46:55 amMDW - PWM
1 stop6h 30mSouthwest
Deal found 4/1$229
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.
mié. 4/305:32 amPWM - ORD
2 stops9h 58mDelta
mié. 5/77:00 amORD - PWM
1 stop5h 50mDelta
Deal found 4/2$234
This Mytrip deal was found by Cheapflights users on 3/31. 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.
vie. 5/99:30 pmPWM - ORD
1 stop27h 02mFrontier
dom. 5/114:15 pmORD - PWM
1 stop27h 25mFrontier
Deal found 3/31$236
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.
jue. 9/2512:03 pmPWM - ORD
Nonstop3h 00mAmerican Airlines
dom. 9/286:12 amORD - PWM
1 stop6h 01mAmerican Airlines
Deal found 4/2$244
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.
sáb. 5/241:30 pmPWM - MDW
1 stop8h 43mDelta
mié. 5/284:15 pmMDW - PWM
1 stop6h 44mDelta
Deal found 4/2$248
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/95:30 amPWM - ORD
2 stops8h 15mSouthwest
jue. 7/101:50 pmORD - PWM
1 stop9h 15mSouthwest
Deal found 4/2$275
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/510:12 amPWM - MDW
1 stop24h 12mFrontier
dom. 4/1310:19 amMDW - PWM
1 stop26h 51mFrontier
Deal found 4/1$278
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.
mié. 4/307:20 amPWM - STL
1 stop5h 12mAmerican Airlines
mié. 5/74:01 pmSTL - PWM
1 stop6h 54mAmerican Airlines
Deal found 4/2$285
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/216:05 amPWM - STL
2 stops9h 30mDelta
mié. 5/283:40 pmSTL - PWM
1 stop7h 19mDelta
Deal found 4/1$290

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Illinois 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 abril 2, 2025.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.

Fly from

Portland

Fly to

Illinois

Route

Depart

Return

Price

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

lun. 5/12

9:30 pm-12:06 am

1 stop27h 36m

Lambert-St Louis

jue. 5/15

5:45 pm-8:40 pm

1 stop25h 55m

$208

PortlandChicago

PWM - ORD

PWMORD

Portland

mar. 5/6

6:13 am-8:05 am

Nonstop2h 52m

Chicago O'Hare Intl

mar. 5/13

5:55 pm-11:59 pm

1 stop5h 04m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

lun. 5/12

3:35 pm-9:54 pm

1 stop7h 19m

Chicago O'Hare Intl

mar. 5/13

6:15 am-2:40 pm

1 stop7h 25m

$225

PortlandChicago

PWM - MDW

PWMMDW

Portland

vie. 5/2

4:40 pm-8:05 pm

1 stop4h 25m

Chicago Midway

dom. 5/4

6:55 am-2:25 pm

1 stop6h 30m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 5/9

9:30 pm-11:32 pm

1 stop27h 02m

Chicago O'Hare Intl

dom. 5/11

4:15 pm-8:40 pm

1 stop27h 25m

$236

PortlandChicago

PWM - ORD

PWMORD

Portland

sáb. 5/24

1:30 pm-6:48 pm

1 stop6h 18m

Chicago O'Hare Intl

mié. 5/28

1:45 pm-11:59 pm

2 stops9h 14m

$238

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 9/25

12:03 pm-2:03 pm

Nonstop3h 00m

Chicago O'Hare Intl

dom. 9/28

6:12 am-1:13 pm

1 stop6h 01m

$244

PortlandChicago

PWM - MDW

PWMMDW

Portland

sáb. 5/24

1:30 pm-9:13 pm

1 stop8h 43m

Chicago Midway

mié. 5/28

4:15 pm-11:59 pm

1 stop6h 44m

$248

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 7/9

5:30 am-12:45 pm

2 stops8h 15m

Chicago O'Hare Intl

jue. 7/10

1:50 pm-12:05 am

1 stop9h 15m

$275

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

mié. 4/30

7:20 am-11:32 am

1 stop5h 12m

Lambert-St Louis

mié. 5/7

4:01 pm-11:55 pm

1 stop6h 54m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 36 results
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Best time to book a flight from Portland to Illinois

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

Cheapflights Insights

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

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

Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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 IL?

Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Illinois as you normally would.

Rainfall in Illinois by month

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

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

Temperature in Illinois by month

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

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

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated abril 2, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Avelo Airlines from Portland to Illinois by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
8,616 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
2,921 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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 Portland to Illinois. 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 Illinois?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Illinois. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $90. American Airlines flights start at $99 while deals on JetBlue start at $102 one-way.

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

    The most popular route from Portland, Maine to Illinois is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Portland - Lambert-St Louis.

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

    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 Illinois on time: Emirates (92%), Air New Zealand (90%), Republic Airways (87%).

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

    Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $194 on average our data indicates $872 when flying from Portland, Maine to Illinois.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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 Portland to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Portland to Illinois

Discover the top 5 airlines that operate flights from Portland to Illinois. 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 abril 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$109FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$399FlexibilityNo cancel feeOn-time71%
DeltaCheapest$189Average$361FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$193Average$441FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$390FlexibilityNo cancel feeOn-time63%

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