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Cheap flights from Portland, Maine to Chicago from $134

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 Chicago departing on 9/13. 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 Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:30 am - 1:00 pm
PWM
-
ORD
7h 30m
1 stop
Delta Logo
6:40 am - 1:07 pm
ORD
-
PWM
5h 27m
1 stop
$299Delta
Wed, Aug 12 - Wed, Aug 19
Delta Logo
4:47 pm - 11:57 pm
PWM
-
ORD
8h 10m
2 stops
Delta Logo
5:40 pm - 11:30 pm
ORD
-
PWM
4h 50m
1 stop
$304Delta
Mon, Aug 17 - Mon, Aug 24
Delta Logo
6:30 am - 3:05 pm
PWM
-
ORD
9h 35m
2 stops
Delta Logo
6:40 am - 4:49 pm
ORD
-
PWM
9h 09m
2 stops
$309Delta
Sat, Sep 26 - Tue, Sep 29
Delta Logo
6:00 am - 11:06 am
PWM
-
ORD
6h 06m
1 stop
Delta Logo
8:55 am - 4:10 pm
ORD
-
PWM
6h 15m
1 stop
$313Delta
Thu, Dec 24 - Wed, Dec 30
United Airlines Logo
6:03 am - 8:00 am
PWM
-
ORD
2h 57mnonstop
United Airlines Logo
5:50 pm - 9:23 pm
ORD
-
PWM
2h 33mnonstop
$315United Airlines
Thu, Aug 13 - Wed, Aug 19
JetBlue Logo
2:40 pm - 9:58 pm
PWM
-
ORD
8h 18m
1 stop
JetBlue Logo
6:00 am - 12:30 pm
ORD
-
PWM
5h 30m
1 stop
$318JetBlue
Wed, Aug 12 - Mon, Aug 17
United Airlines Logo
5:08 pm - 7:05 pm
PWM
-
ORD
2h 57mnonstop
United Airlines Logo
10:55 am - 2:20 pm
ORD
-
PWM
2h 25mnonstop
$323United Airlines
Thu, Nov 5 - Sun, Nov 8
United Airlines Logo
5:15 am - 9:38 am
PWM
-
ORD
5h 23m
1 stop
United Airlines Logo
2:00 pm - 5:42 pm
ORD
-
PWM
2h 42mnonstop
$325United Airlines
Wed, Aug 12 - Tue, Aug 18
Delta Logo
6:00 am - 5:01 pm
PWM
-
ORD
12h 01m
1 stop
Delta Logo
7:05 am - 12:10 pm
ORD
-
PWM
4h 05m
1 stop
$326Delta
Thu, Sep 3 - Fri, Sep 11
United Airlines Logo
5:03 pm - 7:00 pm
PWM
-
ORD
2h 57mnonstop
United Airlines Logo
11:00 am - 2:34 pm
ORD
-
PWM
2h 34mnonstop
$327United Airlines
Thu, Aug 20 - Mon, Aug 24

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Delta flights from Portland, Maine to Chicago O'Hare Intl Airport

Our best Delta deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
Delta
Aug 12
PWM6:30 amPortland
7h 30m
1 stop
ORD1:00 pmChicago O'Hare Intl
Aug 19
ORD6:40 amChicago O'Hare Intl
5h 27m
1 stop
PWM1:07 pmPortland
$299
Delta
Aug 17
PWM4:47 pmPortland
8h 10m
2 stops
ORD11:57 pmChicago O'Hare Intl
Aug 24
ORD5:40 pmChicago O'Hare Intl
4h 50m
1 stop
PWM11:30 pmPortland
$304
Delta
Sep 26
PWM6:30 amPortland
9h 35m
2 stops
ORD3:05 pmChicago O'Hare Intl
Sep 29
ORD6:40 amChicago O'Hare Intl
9h 09m
2 stops
PWM4:49 pmPortland
$309

American Airlines flights from Portland, Maine to Chicago O'Hare Intl Airport

Our best American Airlines deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 4
PWM5:13 pmPortland
5h 58m
1 stop
ORD10:11 pmChicago O'Hare Intl
Sep 6
ORD1:59 pmChicago O'Hare Intl
2h 33m
PWM5:32 pmPortland
$328
American Airlines
Aug 12
PWM6:02 amPortland
5h 28m
1 stop
ORD10:30 amChicago O'Hare Intl
Aug 18
ORD5:00 amChicago O'Hare Intl
4h 31m
1 stop
PWM10:31 amPortland
$335
American Airlines
Sep 5
PWM4:07 pmPortland
3h 07m
ORD6:14 pmChicago O'Hare Intl
Sep 8
ORD7:13 pmChicago O'Hare Intl
2h 35m
PWM10:48 pmPortland
$336

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Chicago O'Hare Intl Airport 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 July 21, 2026.
Use the filters below to find and compare flights from Portland, Maine to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/12

6:30 am-1:00 pm

1 stop7h 30m

Chicago O'Hare Intl

Wed 8/19

6:40 am-1:07 pm

1 stop5h 27m

$299

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 8/17

4:47 pm-11:57 pm

2 stops8h 10m

Chicago O'Hare Intl

Mon 8/24

5:40 pm-11:30 pm

1 stop4h 50m

$304

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 9/26

6:30 am-3:05 pm

2 stops9h 35m

Chicago O'Hare Intl

Tue 9/29

6:40 am-4:49 pm

2 stops9h 09m

$309

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 12/24

6:00 am-11:06 am

1 stop6h 06m

Chicago O'Hare Intl

Wed 12/30

8:55 am-4:10 pm

1 stop6h 15m

$313

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 8/13

6:03 am-8:00 am

Nonstop2h 57m

Chicago O'Hare Intl

Wed 8/19

5:50 pm-9:23 pm

Nonstop2h 33m

$315

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/12

2:40 pm-9:58 pm

1 stop8h 18m

Chicago O'Hare Intl

Mon 8/17

6:00 am-12:30 pm

1 stop5h 30m

$318
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/5

5:08 pm-7:05 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 11/8

10:55 am-2:20 pm

Nonstop2h 25m

$323

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/12

5:15 am-9:38 am

1 stop5h 23m

Chicago O'Hare Intl

Tue 8/18

2:00 pm-5:42 pm

Nonstop2h 42m

$325

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/3

6:00 am-5:01 pm

1 stop12h 01m

Chicago O'Hare Intl

Fri 9/11

7:05 am-12:10 pm

1 stop4h 05m

$326

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 8/20

5:03 pm-7:00 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 8/24

11:00 am-2:34 pm

Nonstop2h 34m

$327

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 Chicago from

How to get the cheapest flight ticket from Portland, Maine to Chicago O'Hare Intl Airport

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 typical price of a round-trip flight between Portland, Maine and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $308.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $433. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Portland, Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $619.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Portland, Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $388 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $497. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Portland to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $362 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland, Maine for as low as $282 on momondo.

What cabin class options are available on Portland, Maine to Chicago O'Hare Intl Airport flights?

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

How have Portland, Maine to Chicago O'Hare Intl Airport flight prices changed over time?

As of July 2026, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 117% more expensive when compared to flights at the same time last year.

When to book flights from Portland, Maine to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland, Maine to Chicago O'Hare Intl Airport (PWM to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago O'Hare Intl Airport

Best Price Found

$241

Fastest flight time

2h 57m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland, Maine in the past 72 hours is $241. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $404.
The fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 57m
Direct flights go from Portland, Maine to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Portland, Maine to Chicago O'Hare Intl Airport

  • How far is Portland to Chicago O'Hare Intl by plane?

    There are 899.6 mi between Portland and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 57m.

  • When did momondo last update prices for flights from Portland Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Portland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Portland Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland, Maine to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Portland, Maine to Chicago O'Hare Intl Airport?

Best airlines flying from Portland, Maine to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Portland, Maine to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,832 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
10,011 reviews
Search United Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.8
8,473 reviews
Search Delta flights

  • United Airlines Flights From Portland, Maine to Chicago O'Hare Intl Airport

    United Airlines flies from Portland, Maine to Chicago O'Hare Intl Airport around 9 times per week, with 10,011 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Portland, Maine to Chicago O'Hare Intl Airport in the last 72 hours was $229 (round-trip), much lower than the average airfare cost of $359 for United Airlines flights on this route.

  • American Airlines Flights From Portland, Maine to Chicago O'Hare Intl Airport

    American Airlines is also a popular choice for this route. American Airlines flight deals for Portland, Maine to Chicago O'Hare Intl Airport start from as low as $209 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $327. American Airlines operates 11 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.1/10 across 11,832 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Schaumburg
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Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
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Hammond
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Evanston
South Holland

Why use momondo?

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

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 Chicago for you.

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

momondo does allow users to show only those flights to Chicago from Portland which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Portland to Chicago 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 Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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