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Cheap flights from Portland, Maine to Chicago from $58

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 8/20. 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 Portland, Maine to Chicago

Cheap round-trip flights

United Airlines Logo
6:20 pm - 8:25 pmPWM-ORD
3h 05mnonstop
United Airlines Logo
6:30 pm - 10:01 pmORD-PWM
2h 31mnonstop
$115United Airlines
Find Deal
Thu, Aug 7 - Sat, Aug 9
United Airlines Logo
4:56 pm - 6:47 pmPWM-ORD
2h 51mnonstop
United Airlines Logo
6:25 pm - 9:59 pmORD-PWM
2h 34mnonstop
$123United Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
$131American Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Southwest Logo
5:50 am - 11:50 amPWM-ORD
7h 00m1 stop
Southwest Logo
1:50 pm - 8:00 pmORD-PWM
5h 10m1 stop
$150Southwest
Find Deal
Tue, Sep 9 - Thu, Sep 11
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
$151American Airlines
Find Deal
Fri, Aug 22 - Mon, Aug 25
Southwest Logo
9:05 am - 9:30 pmPWM-ORD
13h 25m2 stops
Southwest Logo
1:50 pm - 8:00 pmORD-PWM
5h 10m1 stop
$155Southwest
Find Deal
Tue, Sep 9 - Thu, Sep 11
JetBlue Logo
2:17 pm - 8:49 pmPWM-ORD
7h 32m1 stop
JetBlue Logo
6:45 am - 1:22 pmORD-PWM
5h 37m1 stop
$183JetBlue
Find Deal
Fri, Sep 5 - Mon, Sep 8
JetBlue Logo
6:05 am - 11:18 amPWM-ORD
6h 13m1 stop
JetBlue Logo
6:10 am - 1:23 pmORD-PWM
6h 13m1 stop
$193JetBlue
Find Deal
Wed, Jul 30 - Tue, Aug 5
Delta Logo
2:36 pm - 9:53 pmPWM-ORD
8h 17m1 stop
Delta Logo
3:30 pm - 12:03 amORD-PWM
7h 33m1 stop
$217Delta
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Fri, Aug 22 - Mon, Aug 25
Delta Logo
5:00 pm - 11:56 pmPWM-ORD
7h 56m2 stops
Delta Logo
7:15 am - 12:08 pmORD-PWM
3h 53m1 stop
$222Delta
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Fri, Aug 22 - Sun, Aug 24

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
Aug 27
PWM6:30 amPortland
3h 02m
ORD8:32 amChicago O'Hare Intl
Aug 30
ORD8:13 pmChicago O'Hare Intl
2h 46m
PWM11:59 pmPortland
$131
Find similar
American Airlines
Aug 22
PWM6:30 amPortland
3h 02m
ORD8:32 amChicago O'Hare Intl
Aug 25
ORD8:13 pmChicago O'Hare Intl
2h 46m
PWM11:59 pmPortland
$151
Find similar
American Airlines
Sep 17
PWM7:05 amPortland
9h 55m
1 stop
ORD4:00 pmChicago O'Hare Intl
Oct 8
ORD11:30 amChicago O'Hare Intl
2h 26m
PWM2:56 pmPortland
$166
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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 22
PWM2:36 pmPortland
8h 17m
1 stop
ORD9:53 pmChicago O'Hare Intl
Aug 25
ORD3:30 pmChicago O'Hare Intl
7h 33m
1 stop
PWM12:03 amPortland
$217
Find similar
Delta
Aug 22
PWM5:00 pmPortland
7h 56m
2 stops
ORD11:56 pmChicago O'Hare Intl
Aug 24
ORD7:15 amChicago O'Hare Intl
3h 53m
1 stop
PWM12:08 pmPortland
$222
Find similar
Delta
Aug 27
PWM6:00 amPortland
7h 45m
2 stops
ORD12:45 pmChicago O'Hare Intl
Aug 30
ORD2:00 pmChicago O'Hare Intl
9h 03m
2 stops
PWM12:03 amPortland
$227
Find similar

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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $303.

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 Thursday when prices can be found for as low as $443. 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 $636.

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 $158 when looking at flights departing in the evening. 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 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 $375 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 $155 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 July 2025, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 46% 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

$58

Fastest flight time

2h 51m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland, Maine in the past 72 hours is $58. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $115.
The fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 51m
Direct flights go from Portland, Maine to Chicago O'Hare Intl Airport every day.
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  • 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 51m.

  • 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
FrontierPriceFrom $39Free CancellationRating
5.9
3,271 reviews
Search Frontier flights
DeltaPriceFrom $124Free CancellationRating
8.0
7,952 reviews
Search Delta flights
American AirlinesPriceFrom $186Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
8,846 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 16 times per week, with 8,846 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 $209 (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 $186 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $311. American Airlines operates 14 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.2/10 across 10,000 reviews.

Traveling to a place near Chicago?

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

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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