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Cheap flights from Portland, Maine to Illinois from $110

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 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Portland, Maine to Illinois

Cheap round-trip flights

American Airlines Logo
3:28 pm - 5:24 pmPWM-ORD
2h 56mnonstop
American Airlines Logo
11:30 am - 2:56 pmORD-PWM
2h 26mnonstop
$225American Airlines
Find Deal
Tue, Oct 28 - Fri, Oct 31
United Airlines Logo
6:14 am - 8:05 amPWM-ORD
2h 51mnonstop
United Airlines Logo
11:05 am - 2:33 pmORD-PWM
2h 28mnonstop
$231United Airlines
Find Deal
Tue, Oct 21 - Wed, Oct 22
American Airlines Logo
3:38 pm - 9:10 pmPWM-ORD
6h 32m1 stop
American Airlines Logo
11:30 am - 2:56 pmORD-PWM
2h 26mnonstop
$235American Airlines
Find Deal
Tue, Oct 28 - Fri, Oct 31
JetBlue Logo
2:17 pm - 8:49 pmPWM-ORD
7h 32m1 stop
JetBlue Logo
1:36 pm - 11:04 pmORD-PWM
8h 28m1 stop
$237JetBlue
Find Deal
Thu, Oct 2 - Tue, Oct 7
Southwest Logo
4:45 pm - 6:20 pmPWM-MDW
2h 35mnonstop
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$241Southwest
Find Deal
Sat, Nov 1 - Tue, Nov 4
United Airlines Logo
7:25 pm - 11:15 pmPWM-ORD
4h 50m1 stop
United Airlines Logo
6:10 pm - 9:44 pmORD-PWM
2h 34mnonstop
$241United Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
5:25 pm - 8:50 pmPWM-MDW
4h 25m1 stop
Southwest Logo
12:50 pm - 4:00 pmMDW-PWM
2h 10mnonstop
$244Southwest
Find Deal
Tue, Oct 28 - Fri, Oct 31
JetBlue Logo
7:09 am - 6:23 pmPWM-ORD
12h 14m1 stop
JetBlue Logo
6:45 am - 1:22 pmORD-PWM
5h 37m1 stop
$247JetBlue
Find Deal
Sat, Oct 4 - Tue, Oct 7
Delta Logo
4:48 pm - 8:23 pmPWM-ORD
4h 35m1 stop
Delta Logo
6:45 am - 4:00 pmORD-PWM
8h 15m2 stops
$256Delta
Find Deal
Sat, Nov 8 - Wed, Nov 12
Delta Logo
12:45 pm - 6:25 pmPWM-MDW
6h 40m1 stop
Delta Logo
1:08 pm - 12:05 amMDW-PWM
9h 57m2 stops
$259Delta
Find Deal
Tue, Oct 28 - Fri, Oct 31

American Airlines flights from Portland, Maine to Illinois

Our best American Airlines deals on Portland, Maine to Illinois flight tickets
American Airlines
Oct 28
PWM3:28 pmPortland
2h 56m
ORD5:24 pmChicago O'Hare Intl
Oct 31
ORD11:30 amChicago O'Hare Intl
2h 26m
PWM2:56 pmPortland
$225
Find similar
American Airlines
Oct 28
PWM3:38 pmPortland
6h 32m
1 stop
ORD9:10 pmChicago O'Hare Intl
Oct 31
ORD11:30 amChicago O'Hare Intl
2h 26m
PWM2:56 pmPortland
$235
Find similar
American Airlines
Oct 28
PWM1:05 pmPortland
9h 20m
1 stop
ORD9:25 pmChicago O'Hare Intl
Oct 31
ORD8:20 pmChicago O'Hare Intl
14h 48m
1 stop
PWM12:08 pmPortland
$238
Find similar

JetBlue flights from Portland, Maine to Illinois

Our best JetBlue deals on Portland, Maine to Illinois flight tickets
JetBlue
Oct 2
PWM2:17 pmPortland
7h 32m
1 stop
ORD8:49 pmChicago O'Hare Intl
Oct 7
ORD1:36 pmChicago O'Hare Intl
8h 28m
1 stop
PWM11:04 pmPortland
$237
Find similar
JetBlue
Oct 4
PWM7:09 amPortland
12h 14m
1 stop
ORD6:23 pmChicago O'Hare Intl
Oct 7
ORD6:45 amChicago O'Hare Intl
5h 37m
1 stop
PWM1:22 pmPortland
$247
Find similar
JetBlue
Oct 15
PWM7:30 amPortland
5h 40m
1 stop
ORD12:10 pmChicago O'Hare Intl
Oct 21
ORD1:36 pmChicago O'Hare Intl
8h 28m
1 stop
PWM11:04 pmPortland
$269
Find similar

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 September 16, 2025.
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

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/28

3:28 pm-5:24 pm

Nonstop2h 56m

Chicago O'Hare Intl

Fri 10/31

11:30 am-2:56 pm

Nonstop2h 26m

$225

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/21

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Wed 10/22

11:05 am-2:33 pm

Nonstop2h 28m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/28

3:38 pm-9:10 pm

1 stop6h 32m

Chicago O'Hare Intl

Fri 10/31

11:30 am-2:56 pm

Nonstop2h 26m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 10/2

2:17 pm-8:49 pm

1 stop7h 32m

Chicago O'Hare Intl

Tue 10/7

1:36 pm-11:04 pm

1 stop8h 28m

$237

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 11/1

4:45 pm-6:20 pm

Nonstop2h 35m

Chicago Midway

Tue 11/4

6:40 am-12:10 pm

1 stop4h 30m

$241

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/14

7:25 pm-11:15 pm

1 stop4h 50m

Chicago O'Hare Intl

Tue 10/21

6:10 pm-9:44 pm

Nonstop2h 34m

$241

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

5:25 pm-8:50 pm

1 stop4h 25m

Chicago Midway

Fri 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$244

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 10/4

7:09 am-6:23 pm

1 stop12h 14m

Chicago O'Hare Intl

Tue 10/7

6:45 am-1:22 pm

1 stop5h 37m

$247

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 11/8

4:48 pm-8:23 pm

1 stop4h 35m

Chicago O'Hare Intl

Wed 11/12

6:45 am-4:00 pm

2 stops8h 15m

$256

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

12:45 pm-6:25 pm

1 stop6h 40m

Chicago Midway

Fri 10/31

1:08 pm-12:05 am

2 stops9h 57m

$259

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 $281, 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 May is also cheap. Prices for this month can be found on momondo for an average of $304.

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 Thursday when prices can be found for as low as $440. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $621. 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 $393. Flights in the morning are often more expensive with an average ticket price of $495.

What is the cheapest Portland to Illinois flight route?

Fly from Portland to Chicago Midway for the best Portland - Illinois flight prices

How far in advance should I book a flight 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 $379 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 $228 on momondo.

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

There are 4 cabin classes available to choose from on Portland 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

$203

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Illinois

2 airports
The best one-way flight to Illinois from Portland, Maine in the past 72 hours is $203. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $327.
The fastest flight from Portland, Maine to Illinois takes 2h 30m
Direct flights go from Portland, Maine to Illinois every day.
There are 2 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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
DeltaPriceFrom $124Free CancellationRating
7.9
7,957 reviews
Search Delta flights
American AirlinesPriceFrom $200Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,242 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.

An easier way to manage your Illinois trip

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