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Cheap flights from Portland, Maine to Chicago 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 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.
9:13 pm - 10:28 amPWM-ORD
14h 15m1 stop
6:30 am - 10:23 amORD-PWM
26h 53m1 stop
$158Frontier
Find Deal
Mon, Dec 16 - Thu, Dec 19
9:13 pm - 5:54 pmPWM-MDW
21h 41m1 stop
5:52 pm - 10:23 amMDW-PWM
15h 31m1 stop
$158Frontier
Find Deal
Mon, Dec 16 - Thu, Dec 19
5:24 am - 11:03 amPWM-ORD
6h 39m1 stop
4:06 pm - 11:59 pmORD-PWM
6h 53m1 stop
$178American Airlines
Find Deal
Mon, Dec 9 - Wed, Dec 11
5:24 am - 10:58 amPWM-ORD
6h 34m1 stop
4:45 pm - 10:24 pmORD-PWM
4h 39m1 stop
$198American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
6:00 pm - 9:27 pmORD-PWM
2h 27mnonstop
$209United Airlines
Find Deal
Tue, May 6 - Sat, May 10
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
2:45 pm - 8:28 pmORD-PWM
4h 43m1 stop
$219United Airlines
Find Deal
Tue, May 6 - Sat, May 10
5:05 am - 8:50 amPWM-MDW
4h 45m1 stop
5:03 pm - 12:10 amMDW-PWM
6h 07m1 stop
$228Delta
Find Deal
Tue, Dec 31 - Sat, Jan 4
5:05 am - 9:24 amPWM-ORD
5h 19m1 stop
1:45 pm - 12:08 amORD-PWM
9h 23m2 stops
$233Delta
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:10 pm - 10:00 pmPWM-MDW
4h 50m1 stop
10:05 am - 3:15 pmMDW-PWM
4h 10m1 stop
$343Southwest
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:10 pm - 11:05 pmPWM-MDW
8h 55m2 stops
7:20 am - 12:35 pmMDW-PWM
4h 15m1 stop
$348Southwest
Find Deal
Fri, Dec 13 - Tue, Dec 17
8:01 pm - 9:24 amPWM-ORD
14h 23m1 stop
$60Frontier
Find Deal
Tue, Dec 17
8:01 pm - 9:55 amPWM-MDW
14h 54m1 stop
$61Frontier
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Tue, Dec 17
4:50 pm - 10:04 pmPWM-ORD
6h 14m1 stop
$84American Airlines
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Tue, Jan 7
5:50 am - 12:20 pmPWM-ORD
7h 30m1 stop
$99American Airlines
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Sat, Dec 14
5:25 pm - 10:36 pmPWM-ORD
6h 11m1 stop
$114Delta
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Tue, Feb 11
5:05 am - 8:58 amPWM-MDW
4h 53m1 stop
$114Delta
Find Deal
Sat, Dec 14
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
$133United Airlines
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Tue, Dec 31
7:16 pm - 11:25 pmPWM-ORD
5h 09m1 stop
$148United Airlines
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Thu, Dec 26
4:20 pm - 9:30 pmPWM-ORD
6h 10m1 stop
$154Southwest
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Tue, Feb 18
3:35 pm - 9:25 pmPWM-MDW
6h 50m1 stop
$154Southwest
Find Deal
Fri, Jan 24
6:00 am - 2:15 pmPWM-MDW
9h 15m1 stop
5:25 am - 10:40 amMDW-PWM
4h 15m1 stop
$343Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 26
1:15 pm - 9:25 pmPWM-MDW
9h 10m2 stops
5:25 am - 10:40 amMDW-PWM
4h 15m1 stop
$348Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 26
5:54 pm - 5:41 pmPWM-ORD
24h 47m1 stop
5:05 am - 7:12 pmORD-PWM
13h 07m1 stop
$398Frontier
Find Deal
Fri, Nov 15 - Sun, Nov 17
3:10 pm - 9:30 pmPWM-ORD
7h 20m1 stop
5:45 am - 11:05 amORD-PWM
4h 20m1 stop
$403Southwest
Find Deal
Mon, Nov 18 - Fri, Nov 22
5:18 pm - 10:05 pmPWM-ORD
5h 47m1 stop
6:01 am - 12:00 pmORD-PWM
4h 59m1 stop
$418American Airlines
Find Deal
Fri, Nov 15 - Mon, Nov 18
6:00 am - 1:53 pmPWM-MDW
8h 53m1 stop
5:42 pm - 11:09 pmMDW-PWM
4h 27m1 stop
$418Delta
Find Deal
Sat, Nov 16 - Mon, Nov 18
6:00 am - 12:21 pmPWM-ORD
7h 21m1 stop
1:35 pm - 11:47 pmORD-PWM
9h 12m2 stops
$423Delta
Find Deal
Sat, Nov 16 - Mon, Nov 18
4:30 pm - 6:42 pmPWM-ORD
3h 12mnonstop
6:14 pm - 11:59 pmORD-PWM
4h 45m1 stop
$479United Airlines
Find Deal
Sat, Nov 16 - Mon, Nov 18
4:30 pm - 6:42 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$609United Airlines
Find Deal
Sat, Nov 16 - Mon, Nov 18
5:18 pm - 10:05 pmPWM-ORD
5h 47m1 stop
8:43 am - 4:40 pmORD-PWM
6h 57m2 stops
$741American Airlines
Find Deal
Fri, Nov 15 - Mon, Nov 18
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
6:00 pm - 9:27 pmORD-PWM
2h 27mnonstop
$209United Airlines
Find Deal
Tue, May 6 - Sat, May 10
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$279United Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$280United Airlines
Find Deal
Thu, Jan 2 - Mon, Jan 6
6:00 am - 8:05 amPWM-ORD
3h 05mnonstop
6:00 pm - 9:27 pmORD-PWM
2h 27mnonstop
$314United Airlines
Find Deal
Thu, Mar 27 - Mon, Mar 31
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$317United Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
4:30 pm - 6:42 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$322United Airlines
Find Deal
Sun, Nov 24 - Fri, Nov 29
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$333United Airlines
Find Deal
Tue, Dec 31 - Sat, Jan 4
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
11:05 am - 2:37 pmORD-PWM
2h 32mnonstop
$336United Airlines
Find Deal
Fri, Dec 20 - Tue, Dec 24
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$369United Airlines
Find Deal
Fri, Dec 6 - Mon, Dec 9
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
$374United Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17

United Airlines flights from Portland, Maine to Chicago

Our best United Airlines deals on Portland, Maine to Chicago flight tickets
United Airlines
May 6
PWM6:00 amPortland
2h 57m
ORD7:57 amChicago O'Hare Intl
May 10
ORD6:00 pmChicago O'Hare Intl
2h 27m
PWM9:27 pmPortland
United Airlines
May 6
PWM6:00 amPortland
2h 57m
ORD7:57 amChicago O'Hare Intl
May 10
ORD2:45 pmChicago O'Hare Intl
4h 43m
1 stop
PWM8:28 pmPortland
United Airlines
Dec 10
PWM11:24 amPortland
5h 30m
1 stop
ORD3:54 pmChicago O'Hare Intl
Dec 11
ORD2:50 pmChicago O'Hare Intl
7h 00m
1 stop
PWM10:50 pmPortland

Delta flights from Portland, Maine to Chicago

Our best Delta deals on Portland, Maine to Chicago flight tickets
Delta
Dec 31
PWM5:05 amPortland
4h 45m
1 stop
MDW8:50 amChicago Midway
Jan 4
MDW5:03 pmChicago Midway
6h 07m
1 stop
PWM12:10 amPortland
Delta
Dec 12
PWM5:05 amPortland
5h 19m
1 stop
ORD9:24 amChicago O'Hare Intl
Dec 16
ORD1:45 pmChicago O'Hare Intl
9h 23m
2 stops
PWM12:08 amPortland
Delta
Dec 10
PWM6:05 amPortland
6h 53m
1 stop
MDW11:58 amChicago Midway
Dec 11
MDW5:50 pmChicago Midway
4h 27m
1 stop
PWM11:17 pmPortland

How to get the cheapest flight ticket from Portland, Maine to Chicago

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 from Portland, Maine to Chicago?

September. The cheapest time of year to fly to Chicago from Portland, Maine is September. Most expensive is April

What is the cheapest day to depart Portland, Maine for Chicago?

Thursday. The cheapest day of the week is typically Thursday. The most expensive is typically Monday

When is the cheapest time to fly from Portland, Maine to Chicago?

In the evening. Portland, Maine to Chicago flights are approximately 67% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago from Portland, Maine?

Frontier. Frontier, Delta, and American Airlines are the most popular carriers operating from Portland, Maine to Chicago

What is the cheapest Portland, Maine to Chicago flight route?

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

How far in advance should you book Portland, Maine to Chicago flights?

39 days before. The cheapest time to buy a flight from Portland, Maine to Chicago is approximately 39 days to departure

How many flights depart from Portland, Maine to Chicago on average per day?

4 flights are operational weekly from Portland, Maine to Chicago as of November 2024. The most popular departure time for this route is 9:00AM, with 50% of flights per day taking off at noon.

How many flights depart from Portland, Maine to Chicago on average per week?

As of November 2024, 28 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Sunday, with 14% of weekly flights taking off on this day.

What cabin class options are available on Portland, Maine to Chicago flights?

There are 3 cabin classes available to choose from on Portland, Maine to Chicago 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 flights?

You could potentially save up to 54% on your flight if you consider stops on a Portland, Maine to Chicago flight.

How have Portland, Maine to Chicago flight prices changed over time?

As of November 2024, prices for Portland, Maine to Chicago flights are approximately 22% cheaper when compared to flights at the same time last year.

When to book flights from Portland, Maine to Chicago

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

Cheap Portland, Maine to Chicago (PWM to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago

Best Price Found

$60

Fastest flight time

2h 57m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $60. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours is $158.
The fastest flight from Portland, Maine to Chicago takes 2h 57m
Direct flights go from Portland, Maine to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Portland to Chicago by plane?

    There are 887.4 mi between Portland and Chicago. Flights usually cover this in 2h 57m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Portland Airport to Chicago?

    Prices for flights from Portland Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Portland Airport to Chicago?

  • How old do you have to be to fly from Portland Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Portland, Maine to Chicago?

  • What is the most popular airline from Portland, Maine to Chicago?


Best airlines flying from Portland, Maine to Chicago

Compare and see reviews for airlines that fly from Portland, Maine to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $38Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $201Free CancellationRating
8.0
8,788 reviews
Search Delta flights
United AirlinesPriceFrom $206Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
  • United Airlines Flights From Portland, Maine to Chicago

    United Airlines is one of the most popular airlines flying from Portland, Maine to Chicago, operating 14 flights/week on average for this route. A good United Airlines flight deal for Portland, Maine to Chicago starts from $206 round-trip, up to an average price of $411. Our users have rated United Airlines at 7.4/10.


Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Chicago from Portland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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?

Of course. momondo tracks the price of Portland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago