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Cheap flights from Portland, Maine to Illinois from $128

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Illinois departing on 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:45 pm - 8:30 pmPWM  Portland-ORD Chicago O'Hare Intl
4h 45m1 stop Detroit Metropolitan Wayne County
Delta Logo
3:40 pm - 11:28 pmORD  Chicago O'Hare Intl-PWM Portland
6h 48m1 stop Atlanta Hartsfield-Jackson
$238Delta
Fri, Sep 11 - Tue, Sep 22
American Airlines Logo
6:00 am - 12:50 pmPWM  Portland-ORD Chicago O'Hare Intl
7h 50m1 stop Washington, D.C. Reagan-National
American Airlines Logo
7:59 pm - 11:47 pmORD  Chicago O'Hare Intl-PWM Portland
2h 48mnonstop
$239American Airlines
Thu, Oct 1 - Sat, Oct 3
United Airlines Logo
7:25 pm - 11:31 pmPWM  Portland-ORD Chicago O'Hare Intl
5h 06m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
6:59 am - 10:40 amORD  Chicago O'Hare Intl-PWM Portland
2h 41mnonstop
$239United Airlines
Sat, Oct 17 - Thu, Oct 22
American Airlines Logo
4:40 pm - 10:30 pmPWM  Portland-ORD Chicago O'Hare Intl
6h 50m1 stop Philadelphia
American Airlines Logo
1:29 pm - 5:04 pmORD  Chicago O'Hare Intl-PWM Portland
2h 35mnonstop
$239American Airlines
Thu, Oct 22 - Sat, Oct 24
Southwest Logo
5:20 am - 10:00 amPWM  Portland-MDW Chicago Midway
5h 40m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 10:55 amMDW  Chicago Midway-PWM Portland
2h 10mnonstop
$240Southwest
Mon, Oct 26 - Wed, Oct 28
Delta Logo
4:20 pm - 9:37 pmPWM  Portland-ORD Chicago O'Hare Intl
6h 17m1 stop New York John F Kennedy Intl
Delta Logo
1:55 pm - 11:17 pmORD  Chicago O'Hare Intl-PWM Portland
8h 22m2 stops Detroit Metropolitan Wayne County New York LaGuardia
$243Delta
Fri, Sep 11 - Tue, Sep 22
Southwest Logo
10:30 am - 4:40 pmPWM  Portland-MDW Chicago Midway
7h 10m1 stop Baltimore/Washington
Southwest Logo
6:30 pm - 9:45 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$245Southwest
Sat, Sep 5 - Sun, Sep 6
United Airlines Logo
7:40 am - 9:43 amPWM  Portland-ORD Chicago O'Hare Intl
3h 03mnonstop
United Airlines Logo
5:50 pm - 9:23 pmORD  Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
$246United Airlines
Thu, Sep 3 - Sun, Sep 6
Multiple Airlines Logo
5:09 pm - 7:44 pmPWM  Portland-ORD Chicago O'Hare Intl
27h 35m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:26 am - 9:08 amORD  Chicago O'Hare Intl-PWM Portland
22h 42m1 stop Orlando
$323Multiple Airlines
Tue, Oct 27 - Sun, Nov 1
JetBlue Logo
6:00 am - 9:58 amPWM  Portland-ORD Chicago O'Hare Intl
4h 58m1 stop New York John F Kennedy Intl
JetBlue Logo
9:38 am - 11:54 pmORD  Chicago O'Hare Intl-PWM Portland
13h 16m2 stops Boston Logan Intl New York John F Kennedy Intl
$328JetBlue
Sat, Sep 19 - Sat, Sep 26

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Delta flights from Portland, Maine to Illinois

Our best Delta deals on Portland, Maine to Illinois flight tickets
Delta
Sep 11
PWM4:45 pmPortland
4h 45m
1 stop
ORD8:30 pmChicago O'Hare Intl
Sep 22
ORD3:40 pmChicago O'Hare Intl
6h 48m
1 stop
PWM11:28 pmPortland
$238
Delta
Sep 11
PWM4:20 pmPortland
6h 17m
1 stop
ORD9:37 pmChicago O'Hare Intl
Sep 22
ORD1:55 pmChicago O'Hare Intl
8h 22m
2 stops
PWM11:17 pmPortland
$243
Delta
Sep 5
PWM6:00 amPortland
11h 51m
2 stops
ORD4:51 pmChicago O'Hare Intl
Sep 9
ORD1:55 pmChicago O'Hare Intl
9h 01m
2 stops
PWM11:56 pmPortland
$248

American Airlines flights from Portland, Maine to Illinois

Our best American Airlines deals on Portland, Maine to Illinois flight tickets
American Airlines
Sep 9
PWM2:03 pmPortland
2h 56m
ORD3:59 pmChicago O'Hare Intl
Sep 16
ORD5:54 pmChicago O'Hare Intl
4h 51m
1 stop
PWM11:45 pmPortland
$239
American Airlines
Sep 5
PWM12:09 pmPortland
3h 00m
ORD2:09 pmChicago O'Hare Intl
Sep 6
ORD8:19 amChicago O'Hare Intl
7h 45m
1 stop
PWM5:04 pmPortland
$245
American Airlines
Sep 19
PWM5:38 pmPortland
3h 21m
ORD7:59 pmChicago O'Hare Intl
Sep 26
ORD9:29 amChicago O'Hare Intl
2h 36m
PWM1:05 pmPortland
$251

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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, momondo users made 832,500 searches. Data last updated August 13, 2026.
Use the filters below to find and compare flights from Portland, Maine to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Fri 9/11

4:45 pm-8:30 pm

1 stop4h 45m

Chicago O'Hare Intl

Tue 9/22

3:40 pm-11:28 pm

1 stop6h 48m

$238

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 10/1

6:00 am-12:50 pm

1 stop7h 50m

Chicago O'Hare Intl

Sat 10/3

7:59 pm-11:47 pm

Nonstop2h 48m

$239

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Sat 10/17

7:25 pm-11:31 pm

1 stop5h 06m

Chicago O'Hare Intl

Thu 10/22

6:59 am-10:40 am

Nonstop2h 41m

$239

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 10/22

4:40 pm-10:30 pm

1 stop6h 50m

Chicago O'Hare Intl

Sat 10/24

1:29 pm-5:04 pm

Nonstop2h 35m

$239

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Mon 10/26

5:20 am-10:00 am

1 stop5h 40m

Chicago Midway

Wed 10/28

7:45 am-10:55 am

Nonstop2h 10m

$240

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Fri 9/11

4:20 pm-9:37 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 9/22

1:55 pm-11:17 pm

2 stops8h 22m

$243

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Sat 9/5

10:30 am-4:40 pm

1 stop7h 10m

Chicago Midway

Sun 9/6

6:30 pm-9:45 pm

Nonstop2h 15m

$245
Quickest round-trip

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 9/3

7:40 am-9:43 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 9/6

5:50 pm-9:23 pm

Nonstop2h 33m

$246

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Tue 10/27

5:09 pm-7:44 pm

2 stops27h 35m

Chicago O'Hare Intl

Sun 11/1

9:26 am-9:08 am

1 stop22h 42m

$323

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Sat 9/19

6:00 am-9:58 am

1 stop4h 58m

Chicago O'Hare Intl

Sat 9/26

9:38 am-11:54 pm

2 stops13h 16m

$328

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Portland, Maine to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Portland, Maine is in September. Flight prices, which tend to average around $324, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $329.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Portland, Maine to Illinois is on a Wednesday when prices can be found for as low as $437. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $623. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Portland, Maine to Illinois during this time can be as low as $391. Flights in the morning are often more expensive with an average ticket price of $497.

What is the cheapest Portland to Illinois flight route?

Fly from Portland to Chicago O'Hare Intl for the best Portland - Illinois flight prices

How far in advance should I book a flight from Portland, Maine to Illinois?

You are more likely to see cheaper flights to Illinois from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $364 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Portland, Maine for as low as $282 on momondo.

What cabin class options are available on Portland, Maine to Illinois flights?

There are 4 cabin classes available to choose from on Portland, Maine to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Portland, Maine to Illinois flights?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Illinois.

Cheap Portland, Maine to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Illinois

Best Price Found

$236

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Portland, Maine in the past 72 hours is $236. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $366.
The fastest flight from Portland, Maine to Illinois takes 2h 30m
Direct flights go from Portland, Maine to Illinois every day.
There are 98 airports in Illinois. From Portland, Maine there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Portland, Maine to Illinois

  • When did momondo last update prices for flights from Portland Airport to Illinois?

    Prices for flights from Portland Airport to Illinois are updated daily.

  • How many operators does momondo search for flights from Portland Airport to Illinois?

  • How old do you have to be to fly from Portland Airport to Illinois?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Portland, Maine to Illinois?

Best airlines flying from Portland, Maine to Illinois

Compare and see reviews for airlines that fly from Portland, Maine to Illinois with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,923 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
10,112 reviews
Search United Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.8
8,502 reviews
Search Delta flights
SouthwestPriceFrom $267Free CancellationRating
8.0
4,219 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Illinois?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Illinois for you.

Can I find flights from Portland to Illinois with flexible booking policies on momondo?

Flights from Portland to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Illinois?

Once you have performed a search for Portland to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Portland to Illinois right now. Can momondo alert me if prices change?

Price alerts on flights to Illinois from Portland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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