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Cheap flights from Portland, Maine to Chicago O'Hare Intl Airport from $60

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 O'Hare Intl Airport departing on 12/17. 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

These are some of the best round-trip flight deals from Portland, Maine to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Portland, Maine to Chicago.

Cheap last minute flights

Planning a quick getaway from Portland, Maine to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Portland, Maine to Chicago

Find recent round-trip train or bus tickets from Portland, Maine to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:23 am - 10:50 pmPWM-ORD
12h 27m1 stop
10:59 am - 8:12 pmORD-PWM
8h 13m1 stop
$188Frontier
Find Deal
Mon, Jan 6 - Fri, Jan 10
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
2:20 pm - 10:30 pmORD-PWM
7h 10m1 stop
$219United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
4:46 pm - 8:53 pmPWM-ORD
5h 07m1 stop
7:00 am - 2:22 pmORD-PWM
6h 22m1 stop
$228Delta
Find Deal
Thu, Jan 9 - Mon, Jan 13
5:25 pm - 10:36 pmPWM-ORD
6h 11m1 stop
6:55 am - 4:43 pmORD-PWM
8h 48m2 stops
$233Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
11:05 am - 2:37 pmORD-PWM
2h 32mnonstop
$236United Airlines
Find Deal
Wed, Dec 25 - Tue, Dec 31
5:03 pm - 10:08 pmPWM-ORD
6h 05m1 stop
4:21 pm - 10:46 pmORD-PWM
5h 25m1 stop
$248American Airlines
Find Deal
Fri, Dec 6 - Mon, Dec 9
5:50 am - 10:57 amPWM-ORD
6h 07m1 stop
5:15 pm - 10:46 pmORD-PWM
4h 31m1 stop
$257American Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
11:23 am - 10:50 pmPWM-ORD
12h 27m1 stop
6:30 am - 10:23 amORD-PWM
26h 53m1 stop
$363Frontier
Find Deal
Mon, Dec 23 - Sun, Dec 29
1:15 pm - 10:00 pmPWM-ORD
9h 45m2 stops
4:00 pm - 12:05 amORD-PWM
7h 05m1 stop
$373Southwest
Find Deal
Mon, Dec 16 - Mon, Dec 23
6:00 am - 1:00 pmPWM-ORD
8h 00m2 stops
5:45 am - 12:35 pmORD-PWM
5h 50m1 stop
$377Southwest
Find Deal
Tue, Dec 31 - Wed, Jan 1
8:01 pm - 9:24 amPWM-ORD
14h 23m1 stop
$60Frontier
Find Deal
Tue, Dec 17
11:23 am - 10:50 pmPWM-ORD
12h 27m1 stop
$80Frontier
Find Deal
Mon, Dec 23
5:56 pm - 4:06 pmPWM-ORD
23h 10m2 stops
Mon, Dec 9
5:25 pm - 10:36 pmPWM-ORD
6h 11m1 stop
$114Delta
Find Deal
Wed, Feb 19
6:05 am - 4:30 pmPWM-ORD
11h 25m2 stops
$119Delta
Find Deal
Wed, Dec 18
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
$131United Airlines
Find Deal
Wed, Dec 25
6:01 am - 11:40 amPWM-ORD
6h 39m1 stop
$134United Airlines
Find Deal
Sat, Mar 8
6:14 pm - 7:47 amPWM-ORD
14h 33m2 stops
Mon, Jan 6
5:39 am - 12:07 pmPWM-ORD
7h 28m1 stop
$163American Airlines
Find Deal
Sat, Jan 4
5:50 am - 11:13 amPWM-ORD
6h 23m1 stop
$203American Airlines
Find Deal
Thu, Nov 28
6:00 am - 10:50 amPWM-ORD
5h 50m1 stop
5:45 pm - 11:47 pmORD-PWM
5h 02m1 stop
$358Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
5:00 am - 12:50 pmPWM-ORD
8h 50m2 stops
3:35 pm - 11:47 pmORD-PWM
7h 12m1 stop
$363Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
6:10 am - 4:33 pmPWM-ORD
11h 23m2 stops
1:31 pm - 11:09 pmORD-PWM
8h 38m2 stops
$368Delta
Find Deal
Mon, Nov 25 - Wed, Nov 27
5:30 am - 9:49 amPWM-ORD
5h 19m1 stop
6:00 pm - 9:30 pmORD-PWM
2h 30mnonstop
$409United Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:00 am - 10:04 amPWM-ORD
6h 04m1 stop
8:25 am - 4:18 pmORD-PWM
6h 53m1 stop
$418Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24
11:25 am - 3:43 pmPWM-ORD
5h 18m1 stop
6:00 pm - 9:30 pmORD-PWM
2h 30mnonstop
$419United Airlines
Find Deal
Sat, Nov 23 - Wed, Nov 27
5:30 am - 1:00 pmPWM-ORD
8h 30m2 stops
11:25 am - 11:55 pmORD-PWM
11h 30m2 stops
$428Southwest
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:30 am - 2:00 pmPWM-ORD
9h 30m1 stop
7:30 am - 12:05 amORD-PWM
15h 35m2 stops
$433Southwest
Find Deal
Sun, Nov 24 - Mon, Dec 2
12:30 pm - 7:17 pmPWM-ORD
7h 47m1 stop
5:25 pm - 10:47 pmORD-PWM
4h 22m1 stop
$447American Airlines
Find Deal
Sun, Nov 24 - Mon, Dec 2
12:59 pm - 5:29 pmPWM-ORD
5h 30m1 stop
2:55 pm - 10:47 pmORD-PWM
6h 52m1 stop
$533American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
11:05 am - 2:37 pmORD-PWM
2h 32mnonstop
$236United Airlines
Find Deal
Wed, Dec 25 - Tue, Dec 31
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$244United Airlines
Find Deal
Thu, Jan 9 - Sat, Jan 11
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$258United Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$265United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$269United Airlines
Find Deal
Wed, Jan 8 - Sat, Jan 11
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$279United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$280United Airlines
Find Deal
Sat, Dec 14 - Wed, Dec 18
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$301United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$314United Airlines
Find Deal
Tue, Dec 31 - Sat, Jan 4
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$324United Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10

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

Our best Frontier deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
Frontier
Jan 6
PWM11:23 amPortland
12h 27m
1 stop
ORD10:50 pmChicago O'Hare Intl
Jan 10
ORD10:59 amChicago O'Hare Intl
8h 13m
1 stop
PWM8:12 pmPortland
Frontier
Dec 23
PWM11:23 amPortland
12h 27m
1 stop
ORD10:50 pmChicago O'Hare Intl
Dec 29
ORD6:30 amChicago O'Hare Intl
26h 53m
1 stop
PWM10:23 amPortland
Frontier
Dec 23
PWM11:23 amPortland
12h 27m
1 stop
ORD10:50 pmChicago O'Hare Intl
Dec 26
ORD10:59 amChicago O'Hare Intl
6h 50m
1 stop
PWM6:49 pmPortland

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
Jan 11
PWM4:10 pmPortland
3h 14m
ORD6:24 pmChicago O'Hare Intl
Jan 18
ORD2:20 pmChicago O'Hare Intl
7h 10m
1 stop
PWM10:30 pmPortland
United Airlines
Dec 25
PWM7:30 amPortland
3h 14m
ORD9:44 amChicago O'Hare Intl
Dec 31
ORD11:05 amChicago O'Hare Intl
2h 32m
PWM2:37 pmPortland
United Airlines
Jan 8
PWM4:10 pmPortland
3h 14m
ORD6:24 pmChicago O'Hare Intl
Jan 11
ORD9:10 amChicago O'Hare Intl
6h 42m
1 stop
PWM4:52 pmPortland

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 $319.

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 $321. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $413.

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 $127 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $386. 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?

In general, most travelers find the cheapest time to book a flight to Chicago O'Hare Intl Airport is about 57 days prior to their departure date when tickets on average are $401. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $94.

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.

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

You could potentially save up to 23% 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 November 2024, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 10% 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

$60

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 $60. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $188.
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.

  • 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
FrontierPriceFrom $38Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $204Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $206Free CancellationRating
8.0
8,755 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 14 times per week, with 9,172 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 $204 (round-trip), much lower than the average airfare cost of $409 for United Airlines flights on this route.


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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