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Cheap flights from Illinois to Portland from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Portland departing on 11/27. 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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Find the cheapest flights from Illinois to Portland

Cheap round-trip flights

JetBlue Logo
1:36 pm - 10:02 pmORD-PWM
7h 26m1 stop
JetBlue Logo
7:09 am - 12:10 pmPWM-ORD
6h 01m1 stop
$183JetBlue
Find Deal
Fri, Sep 5 - Tue, Sep 9
JetBlue Logo
6:10 am - 1:22 pmORD-PWM
6h 12m1 stop
JetBlue Logo
7:30 am - 12:10 pmPWM-ORD
5h 40m1 stop
$193JetBlue
Find Deal
Wed, Sep 3 - Tue, Sep 9
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
American Airlines Logo
2:13 pm - 4:10 pmPWM-ORD
2h 57mnonstop
$215American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
American Airlines Logo
6:00 am - 11:06 amPWM-ORD
6h 06m1 stop
$225American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
United Airlines Logo
1:55 pm - 5:42 pmORD-PWM
2h 47mnonstop
United Airlines Logo
6:23 pm - 8:23 pmPWM-ORD
3h 00mnonstop
$229United Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
1:40 pm - 4:50 pmMDW-PWM
2h 10mnonstop
Southwest Logo
4:45 pm - 6:20 pmPWM-MDW
2h 35mnonstop
$231Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
Delta Logo
3:30 pm - 12:03 amORD-PWM
7h 33m1 stop
Delta Logo
7:00 am - 1:09 pmPWM-ORD
7h 09m1 stop
$235Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
United Airlines Logo
6:25 pm - 9:59 pmORD-PWM
2h 34mnonstop
United Airlines Logo
7:40 pm - 11:15 pmPWM-ORD
4h 35m1 stop
$239United Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Delta Logo
3:30 pm - 12:03 amORD-PWM
7h 33m1 stop
Delta Logo
7:00 am - 4:38 pmPWM-ORD
10h 38m2 stops
$240Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Southwest Logo
5:35 am - 11:15 amMDW-PWM
4h 40m1 stop
Southwest Logo
4:45 pm - 6:20 pmPWM-MDW
2h 35mnonstop
$241Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25

JetBlue flights from Illinois to Portland, Maine

Our best JetBlue deals on Illinois to Portland, Maine flight tickets
JetBlue
Sep 5
ORD1:36 pmChicago O'Hare Intl
7h 26m
1 stop
PWM10:02 pmPortland
Sep 9
PWM7:09 amPortland
6h 01m
1 stop
ORD12:10 pmChicago O'Hare Intl
$183
Find similar
JetBlue
Sep 3
ORD6:10 amChicago O'Hare Intl
6h 12m
1 stop
PWM1:22 pmPortland
Sep 9
PWM7:30 amPortland
5h 40m
1 stop
ORD12:10 pmChicago O'Hare Intl
$193
Find similar
JetBlue
Sep 22
ORD6:45 amChicago O'Hare Intl
5h 37m
1 stop
PWM1:22 pmPortland
Sep 29
PWM7:09 amPortland
6h 12m
1 stop
ORD12:21 pmChicago O'Hare Intl
$198
Find similar

American Airlines flights from Illinois to Portland, Maine

Our best American Airlines deals on Illinois to Portland, Maine flight tickets
American Airlines
Aug 30
ORD8:13 pmChicago O'Hare Intl
2h 46m
PWM11:59 pmPortland
Sep 6
PWM2:13 pmPortland
2h 57m
ORD4:10 pmChicago O'Hare Intl
$215
Find similar
American Airlines
Aug 30
ORD8:13 pmChicago O'Hare Intl
2h 46m
PWM11:59 pmPortland
Sep 6
PWM6:00 amPortland
6h 06m
1 stop
ORD11:06 amChicago O'Hare Intl
$225
Find similar
American Airlines
Sep 2
ORD6:45 pmChicago O'Hare Intl
2h 43m
PWM10:28 pmPortland
Sep 9
PWM6:01 amPortland
2h 56m
ORD7:57 amChicago O'Hare Intl
$231
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Portland, Maine 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 11, 2025.
Use the filters below to find and compare flights from Illinois to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

Portland

Tue 9/9

7:09 am-12:10 pm

1 stop6h 01m

$183

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

6:10 am-1:22 pm

1 stop6h 12m

Portland

Tue 9/9

7:30 am-12:10 pm

1 stop5h 40m

$193

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

8:13 pm-11:59 pm

Nonstop2h 46m

Portland

Sat 9/6

2:13 pm-4:10 pm

Nonstop2h 57m

$215

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

8:13 pm-11:59 pm

Nonstop2h 46m

Portland

Sat 9/6

6:00 am-11:06 am

1 stop6h 06m

$225

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/27

1:55 pm-5:42 pm

Nonstop2h 47m

Portland

Sat 8/30

6:23 pm-8:23 pm

Nonstop3h 00m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 10/22

1:40 pm-4:50 pm

Nonstop2h 10m

Portland

Sat 10/25

4:45 pm-6:20 pm

Nonstop2h 35m

$231

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

3:30 pm-12:03 am

1 stop7h 33m

Portland

Sat 9/6

7:00 am-1:09 pm

1 stop7h 09m

$235

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/27

6:25 pm-9:59 pm

Nonstop2h 34m

Portland

Sat 8/30

7:40 pm-11:15 pm

1 stop4h 35m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

3:30 pm-12:03 am

1 stop7h 33m

Portland

Sat 9/6

7:00 am-4:38 pm

2 stops10h 38m

$240

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 10/22

5:35 am-11:15 am

1 stop4h 40m

Portland

Sat 10/25

4:45 pm-6:20 pm

Nonstop2h 35m

$241

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 Portland from

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

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 Portland, Maine?

The cheapest month to fly to Portland, Maine from Illinois is in February. Flight prices, which tend to average around $285, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $303.

What is the cheapest day to depart on your flight to Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Illinois is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $334. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $402.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the evening is the cheapest time of day to fly from Illinois to Portland, Maine when you can find flight prices for as low as $303. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $377. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Illinois to Portland flight route?

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

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

You are more likely to see cheaper flights to Portland, Maine from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $400 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Illinois for as low as $282 on momondo.

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

There are 4 cabin classes available to choose from on Illinois to Portland 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 Illinois to Portland, Maine flights?

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

Cheap Illinois to Portland, Maine flight deals and tips

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

Best Price Found

$100

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Portland, Maine

1 airport
The best one-way flight to Portland, Maine from Illinois in the past 72 hours is $100. The best round-trip flight deal from Illinois to Portland, Maine found on momondo in the last 72 hours is $183.
The fastest flight from Illinois to Portland, Maine takes 2h 10m
Direct flights go from Illinois to Portland, Maine every day.
There is 1 airport near Portland, Maine: Portland (PWM)
Search flight deals

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The required travel and health documents for your Portland Airport 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 Portland Airport. 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 Illinois to Portland, Maine?

Best airlines flying from Illinois to Portland, Maine

Compare and see reviews for airlines that fly from Illinois to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $163Free CancellationRating
8.0
7,979 reviews
Search Delta flights
SouthwestPriceFrom $191Free CancellationRating
8.0
4,248 reviews
Search Southwest flights
United AirlinesPriceFrom $223Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
American AirlinesPriceFrom $230Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Bartlett
Gorham
Brunswick
Auburn
Intervale
Windham
Bath
Falmouth
Georgetown
Oxford
Tamworth

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Portland. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Illinois to Portland 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 Illinois to Portland?

momondo helps you find the best flight between Illinois and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Portland, momondo offers a useful price alert feature which will track prices for flights to Portland from Illinois and alert you when they change.

An easier way to manage your Portland, Maine trip

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