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Cheap flights from Portland, Maine to Chicago from $96

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 4/6. 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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Cheap round-trip flights

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Multiple Airlines Logo
5:40 pm - 8:16 amPWM-ORD
15h 36m1 stop
Multiple Airlines Logo
5:25 am - 9:06 amORD-PWM
26h 41m1 stop
$269Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Multiple Airlines Logo
2:36 pm - 11:28 pmPWM-ORD
9h 52m2 stops
Multiple Airlines Logo
5:25 am - 9:06 amORD-PWM
26h 41m1 stop
$278Multiple Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
Delta Logo
2:35 pm - 11:54 pmPWM-ORD
10h 19m2 stops
Delta Logo
2:45 pm - 9:59 pmORD-PWM
6h 14m1 stop
$304Delta
Find Deal
Sat, Jan 17 - Mon, Jan 19
American Airlines Logo
5:37 pm - 7:50 pmPWM-ORD
3h 13mnonstop
American Airlines Logo
1:40 pm - 5:05 pmORD-PWM
2h 25mnonstop
$311American Airlines
Find Deal
Mon, Nov 10 - Mon, Nov 17
Delta Logo
2:30 pm - 9:55 amPWM-ORD
20h 25m1 stop
Delta Logo
2:35 pm - 11:19 pmORD-PWM
7h 44m1 stop
$313Delta
Find Deal
Thu, Nov 13 - Tue, Nov 18
American Airlines Logo
5:37 pm - 7:50 pmPWM-ORD
3h 13mnonstop
American Airlines Logo
1:40 pm - 5:05 pmORD-PWM
2h 25mnonstop
$316American Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
United Airlines Logo
5:45 am - 7:57 amPWM-ORD
3h 12mnonstop
United Airlines Logo
5:50 pm - 9:14 pmORD-PWM
2h 24mnonstop
$319United Airlines
Find Deal
Fri, Feb 20 - Sun, Mar 1
Southwest Logo
5:30 am - 2:45 pmPWM-ORD
10h 15m2 stops
Southwest Logo
1:45 pm - 12:20 amORD-PWM
9h 35m2 stops
$334Southwest
Find Deal
Wed, Nov 12 - Thu, Nov 13
United Airlines Logo
5:00 pm - 6:55 pmPWM-ORD
2h 55mnonstop
United Airlines Logo
10:53 am - 2:12 pmORD-PWM
2h 19mnonstop
$336United Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Southwest Logo
12:45 pm - 9:50 pmPWM-ORD
10h 05m2 stops
Southwest Logo
6:05 am - 10:15 pmORD-PWM
15h 10m2 stops
$357Southwest
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Wed, Nov 12 - Mon, Nov 17

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
Oct 23
PWM1:05 pmPortland
9h 20m
1 stop
ORD9:25 pmChicago O'Hare Intl
Oct 27
ORD11:13 amChicago O'Hare Intl
8h 01m
1 stop
PWM8:14 pmPortland
$304
Find similar
American Airlines
Nov 10
PWM5:37 pmPortland
3h 13m
ORD7:50 pmChicago O'Hare Intl
Nov 17
ORD1:40 pmChicago O'Hare Intl
2h 25m
PWM5:05 pmPortland
$311
Find similar
American Airlines
Nov 8
PWM5:37 pmPortland
3h 13m
ORD7:50 pmChicago O'Hare Intl
Nov 12
ORD1:40 pmChicago O'Hare Intl
2h 25m
PWM5:05 pmPortland
$316
Find similar

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
Jan 17
PWM2:35 pmPortland
10h 19m
2 stops
ORD11:54 pmChicago O'Hare Intl
Jan 19
ORD2:45 pmChicago O'Hare Intl
6h 14m
1 stop
PWM9:59 pmPortland
$304
Find similar
Delta
Nov 13
PWM2:30 pmPortland
20h 25m
1 stop
ORD9:55 amChicago O'Hare Intl
Nov 18
ORD2:35 pmChicago O'Hare Intl
7h 44m
1 stop
PWM11:19 pmPortland
$313
Find similar
Delta
Nov 13
PWM2:30 pmPortland
28h 23m
1 stop
ORD5:53 pmChicago O'Hare Intl
Nov 17
ORD2:35 pmChicago O'Hare Intl
7h 44m
1 stop
PWM11:19 pmPortland
$318
Find similar

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 October 14, 2025.
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

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 10/30

5:40 pm-8:16 am

1 stop15h 36m

Chicago O'Hare Intl

Sun 11/2

5:25 am-9:06 am

1 stop26h 41m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/31

2:36 pm-11:28 pm

2 stops9h 52m

Chicago O'Hare Intl

Sun 11/2

5:25 am-9:06 am

1 stop26h 41m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/17

2:35 pm-11:54 pm

2 stops10h 19m

Chicago O'Hare Intl

Mon 1/19

2:45 pm-9:59 pm

1 stop6h 14m

$304

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 11/10

5:37 pm-7:50 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 11/17

1:40 pm-5:05 pm

Nonstop2h 25m

$311

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/13

2:30 pm-9:55 am

1 stop20h 25m

Chicago O'Hare Intl

Tue 11/18

2:35 pm-11:19 pm

1 stop7h 44m

$313

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 11/8

5:37 pm-7:50 pm

Nonstop3h 13m

Chicago O'Hare Intl

Wed 11/12

1:40 pm-5:05 pm

Nonstop2h 25m

$316

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 2/20

5:45 am-7:57 am

Nonstop3h 12m

Chicago O'Hare Intl

Sun 3/1

5:50 pm-9:14 pm

Nonstop2h 24m

$319

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 11/12

5:30 am-2:45 pm

2 stops10h 15m

Chicago O'Hare Intl

Thu 11/13

1:45 pm-12:20 am

2 stops9h 35m

$334

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 11/14

5:00 pm-6:55 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 11/17

10:53 am-2:12 pm

Nonstop2h 19m

$336

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 11/12

12:45 pm-9:50 pm

2 stops10h 05m

Chicago O'Hare Intl

Mon 11/17

6:05 am-10:15 pm

2 stops15h 10m

$357

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $297.

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 Friday when prices can be found for as low as $321. 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 $434.

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 in the evening is the least expensive time of day to depart. momondo users have found prices as low as $265 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $353. 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 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 $370 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 $228 on momondo.

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

There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl 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 October 2025, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 19% cheaper 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

$177

Fastest flight time

2h 53m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland, Maine in the past 72 hours is $177. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $325.
The fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 53m
Direct flights go from Portland, Maine to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 55m.

  • 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
DeltaPriceFrom $124Free CancellationRating
7.9
7,975 reviews
Search Delta flights
American AirlinesPriceFrom $203Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
8,976 reviews
Search United Airlines 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 15 times per week, with 8,976 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 $378 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 $203 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $304. American Airlines operates 21 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.2/10 across 11,042 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
Benton Harbor

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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