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Cheap flights from Portland, Maine to Chicago from $149

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.
United Airlines Logo
6:00 am - 7:57 amPWM  Portland-ORD Chicago O'Hare Intl
2h 57mnonstop
United Airlines Logo
10:00 am - 7:24 pmORD  Chicago O'Hare Intl-PWM Portland
8h 24m2 stops New York LaGuardia Washington, D.C. Dulles Intl
$311United Airlines
Tue, Oct 20 - Tue, Oct 20
American Airlines Logo
5:38 pm - 7:59 pmPWM  Portland-ORD Chicago O'Hare Intl
3h 21mnonstop
American Airlines Logo
7:59 pm - 11:43 pmORD  Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
$336American Airlines
Wed, Sep 30 - Wed, Oct 7
United Airlines Logo
5:08 pm - 7:05 pmPWM  Portland-ORD Chicago O'Hare Intl
2h 57mnonstop
United Airlines Logo
6:18 pm - 9:51 pmORD  Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
$337United Airlines
Wed, Nov 4 - Wed, Nov 11
American Airlines Logo
6:30 am - 8:38 amPWM  Portland-ORD Chicago O'Hare Intl
3h 08mnonstop
American Airlines Logo
7:59 pm - 11:47 pmORD  Chicago O'Hare Intl-PWM Portland
2h 48mnonstop
$337American Airlines
Thu, Sep 24 - Sat, Sep 26
United Airlines Logo
8:32 am - 10:32 amPWM  Portland-ORD Chicago O'Hare Intl
3h 00mnonstop
United Airlines Logo
6:18 pm - 9:51 pmORD  Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
$337United Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
7:00 am - 9:04 amPWM  Portland-ORD Chicago O'Hare Intl
3h 04mnonstop
American Airlines Logo
7:59 pm - 11:43 pmORD  Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
$337American Airlines
Thu, Oct 15 - Sat, Oct 17
Multiple Airlines Logo
7:12 pm - 9:48 amPWM  Portland-ORD Chicago O'Hare Intl
15h 36m1 stop Tampa
Multiple Airlines Logo
10:52 am - 9:21 amORD  Chicago O'Hare Intl-PWM Portland
21h 29m1 stop Fort Myers SW Florida Intl
$348Multiple Airlines
Wed, Dec 2 - Mon, Dec 7
Multiple Airlines Logo
10:31 am - 6:14 pmPWM  Portland-ORD Chicago O'Hare Intl
8h 43m1 stop Fort Myers SW Florida Intl
Multiple Airlines Logo
10:52 am - 9:21 amORD  Chicago O'Hare Intl-PWM Portland
21h 29m1 stop Fort Myers SW Florida Intl
$356Multiple Airlines
Thu, Dec 10 - Mon, Dec 14
Delta Logo
6:28 am - 1:08 pmPWM  Portland-ORD Chicago O'Hare Intl
7h 40m1 stop New York LaGuardia
Delta Logo
7:00 am - 11:57 amORD  Chicago O'Hare Intl-PWM Portland
3h 57m1 stop Detroit Metropolitan Wayne County
$357Delta
Thu, Oct 29 - Wed, Nov 4
Delta Logo
1:10 pm - 4:26 pmPWM  Portland-ORD Chicago O'Hare Intl
4h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 pm - 12:10 amORD  Chicago O'Hare Intl-PWM Portland
5h 10m1 stop New York John F Kennedy Intl
$357Delta
Sat, Oct 31 - Mon, Nov 2

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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 30
PWM5:38 pmPortland
3h 21m
ORD7:59 pmChicago O'Hare Intl
Oct 7
ORD7:59 pmChicago O'Hare Intl
2h 44m
PWM11:43 pmPortland
$336
American Airlines
Oct 15
PWM7:00 amPortland
3h 04m
ORD9:04 amChicago O'Hare Intl
Oct 20
ORD8:00 pmChicago O'Hare Intl
2h 40m
PWM11:40 pmPortland
$337
American Airlines
Sep 30
PWM6:00 amPortland
5h 10m
1 stop
ORD10:10 amChicago O'Hare Intl
Oct 7
ORD7:59 pmChicago O'Hare Intl
2h 44m
PWM11:43 pmPortland
$346

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

Our best United Airlines deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 20
PWM6:00 amPortland
2h 57m
ORD7:57 amChicago O'Hare Intl
Oct 20
ORD10:00 amChicago O'Hare Intl
8h 24m
2 stops
PWM7:24 pmPortland
$311
United Airlines
Sep 9
PWM6:00 amPortland
2h 57m
ORD7:57 amChicago O'Hare Intl
Sep 11
ORD11:00 amChicago O'Hare Intl
2h 34m
PWM2:34 pmPortland
$337
United Airlines
Sep 9
PWM6:06 amPortland
7h 02m
1 stop
ORD12:08 pmChicago O'Hare Intl
Sep 11
ORD11:00 amChicago O'Hare Intl
2h 34m
PWM2:34 pmPortland
$347

momondo Fare Finder

 
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 Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Tue 10/20

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Tue 10/20

10:00 am-7:24 pm

2 stops8h 24m

$311

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Wed 9/30

5:38 pm-7:59 pm

Nonstop3h 21m

Chicago O'Hare Intl

Wed 10/7

7:59 pm-11:43 pm

Nonstop2h 44m

$336
Quickest round-trip

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Wed 11/4

5:08 pm-7:05 pm

Nonstop2h 57m

Chicago O'Hare Intl

Wed 11/11

6:18 pm-9:51 pm

Nonstop2h 33m

$337

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 9/24

6:30 am-8:38 am

Nonstop3h 08m

Chicago O'Hare Intl

Sat 9/26

7:59 pm-11:47 pm

Nonstop2h 48m

$337

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Wed 10/28

8:32 am-10:32 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 11/4

6:18 pm-9:51 pm

Nonstop2h 33m

$337

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 10/15

7:00 am-9:04 am

Nonstop3h 04m

Chicago O'Hare Intl

Sat 10/17

7:59 pm-11:43 pm

Nonstop2h 44m

$337

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Wed 12/2

7:12 pm-9:48 am

1 stop15h 36m

Chicago O'Hare Intl

Mon 12/7

10:52 am-9:21 am

1 stop21h 29m

$348

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 12/10

10:31 am-6:14 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 12/14

10:52 am-9:21 am

1 stop21h 29m

$356

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Thu 10/29

6:28 am-1:08 pm

1 stop7h 40m

Chicago O'Hare Intl

Wed 11/4

7:00 am-11:57 am

1 stop3h 57m

$357

PortlandChicago

PWM Portland - ORD Chicago O'Hare Intl

PWMORD

Portland

Sat 10/31

1:10 pm-4:26 pm

1 stop4h 16m

Chicago O'Hare Intl

Mon 11/2

6:00 pm-12:10 am

1 stop5h 10m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

Prices are currently typical for flights on this route.

Typical prices usually range from $279 to $426.
The lowest price recently found on this route was $311.

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 $435. 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 $622.

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 $501. 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 $368 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.

Can stopping save me money on Portland, Maine to Chicago O'Hare Intl Airport flights?

You could potentially save up to 9% on your flight if you consider stops on a Portland, Maine to Chicago O'Hare Intl Airport flight.

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

As of September 2026, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 3% 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

$149

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 $149. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $311.
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
12,044 reviews
Search American Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.8
8,560 reviews
Search Delta flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
10,169 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 17 times per week, with 10,168 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 $235 (round-trip), much lower than the average airfare cost of $376 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 $336. American Airlines operates 18 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.1/10 across 12,043 reviews.

Traveling to a place near Chicago?

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

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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