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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 2/26. 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.
6:48 pm - 1:20 pmPWM-ORD
19h 32m1 stop
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
$192Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
6:48 pm - 1:20 pmPWM-ORD
19h 32m1 stop
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
$193Frontier
Find Deal
Wed, Feb 19 - Wed, Feb 26
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$209United Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
6:01 am - 10:46 amPWM-ORD
5h 45m1 stop
11:10 am - 2:32 pmORD-PWM
2h 22mnonstop
$219United Airlines
Find Deal
Wed, Feb 19 - Wed, Feb 26
4:46 pm - 9:15 pmPWM-ORD
5h 29m1 stop
12:15 pm - 11:51 pmORD-PWM
10h 36m2 stops
$233Delta
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:00 am - 1:28 pmPWM-ORD
8h 28m2 stops
6:15 am - 4:06 pmORD-PWM
8h 51m2 stops
$238Delta
Find Deal
Sat, Jan 18 - Sat, Jan 25
5:24 am - 10:47 amPWM-ORD
6h 23m1 stop
6:00 am - 12:06 pmORD-PWM
5h 06m1 stop
$253American Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
$258American Airlines
Find Deal
Fri, Jun 6 - Thu, Jun 12
6:00 am - 6:10 pmPWM-ORD
13h 10m2 stops
4:35 pm - 10:15 pmORD-PWM
4h 40m1 stop
$338Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
6:00 am - 6:10 pmPWM-ORD
13h 10m2 stops
7:30 am - 11:55 pmORD-PWM
15h 25m2 stops
$343Southwest
Find Deal
Thu, Feb 20 - Fri, Feb 28
6:48 pm - 10:46 pmPWM-MDW
28h 58m1 stop
$60Frontier
Find Deal
Wed, Feb 26
11:23 am - 12:29 pmPWM-MDW
26h 06m1 stop
$65Frontier
Find Deal
Mon, Jan 6
5:23 am - 9:55 amPWM-ORD
5h 32m1 stop
$114Delta
Find Deal
Thu, Jan 23
5:34 am - 11:59 amPWM-MDW
7h 25m1 stop
$114Delta
Find Deal
Wed, Jan 22
5:17 pm - 10:05 pmPWM-ORD
5h 48m1 stop
$124American Airlines
Find Deal
Mon, Jan 6
3:55 pm - 11:09 pmPWM-ORD
8h 14m1 stop
$132United Airlines
Find Deal
Fri, Mar 14
3:55 pm - 11:09 pmPWM-ORD
8h 14m1 stop
$133United Airlines
Find Deal
Fri, Mar 14
12:31 pm - 7:23 pmPWM-ORD
7h 52m1 stop
$134American Airlines
Find Deal
Tue, Feb 18
6:00 am - 3:00 pmPWM-ORD
10h 00m2 stops
$154Southwest
Find Deal
Sun, Jan 26
5:35 am - 10:35 pmPWM-ORD
18h 00m2 stops
$160Southwest
Find Deal
Thu, Feb 27
5:39 am - 12:12 pmPWM-ORD
7h 33m1 stop
6:00 am - 11:53 amORD-PWM
4h 53m1 stop
$323American Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
5:39 am - 12:12 pmPWM-ORD
7h 33m1 stop
6:00 am - 11:53 amORD-PWM
4h 53m1 stop
$372American Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
6:05 am - 1:42 pmPWM-ORD
8h 37m1 stop
5:30 pm - 11:22 pmORD-PWM
4h 52m1 stop
$418Delta
Find Deal
Mon, Dec 23 - Thu, Dec 26
6:05 am - 4:40 pmPWM-ORD
11h 35m2 stops
5:30 pm - 11:22 pmORD-PWM
4h 52m1 stop
$423Delta
Find Deal
Tue, Dec 24 - Thu, Dec 26
6:00 am - 6:10 pmPWM-ORD
13h 10m2 stops
1:45 pm - 12:05 amORD-PWM
9h 20m2 stops
$473Southwest
Find Deal
Tue, Dec 24 - Thu, Dec 26
5:30 am - 2:00 pmPWM-ORD
9h 30m1 stop
2:55 pm - 12:05 amORD-PWM
8h 10m2 stops
$493Southwest
Find Deal
Mon, Dec 23 - Fri, Dec 27
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$609United Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
5:20 am - 9:55 amPWM-ORD
5h 35m1 stop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$619United Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
5:56 pm - 4:06 pmPWM-ORD
23h 10m2 stops
7:30 pm - 5:08 pmORD-PWM
20h 38m2 stops
Fri, Dec 27 - Mon, Dec 30
5:56 pm - 4:06 pmPWM-ORD
23h 10m2 stops
7:53 pm - 5:16 pmORD-PWM
20h 23m3 stops
Fri, Dec 27 - Sun, Dec 29
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$209United Airlines
Find Deal
Sat, Jan 18 - Sat, Jan 25
4:04 pm - 6:10 pmPWM-ORD
3h 06mnonstop
11:10 am - 2:32 pmORD-PWM
2h 22mnonstop
$240United Airlines
Find Deal
Wed, Feb 19 - Wed, Feb 26
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
$258American Airlines
Find Deal
Fri, Jun 6 - Thu, Jun 12
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
12:25 pm - 2:25 pmPWM-ORD
3h 00mnonstop
7:30 am - 10:47 amORD-PWM
2h 17mnonstop
$292United Airlines
Find Deal
Fri, Apr 25 - Fri, May 2
11:58 am - 1:55 pmPWM-ORD
2h 57mnonstop
7:30 am - 10:47 amORD-PWM
2h 17mnonstop
$314United Airlines
Find Deal
Thu, May 8 - Sun, May 11
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
$349United Airlines
Find Deal
Wed, Jan 1 - Sun, Jan 5
4:04 pm - 6:10 pmPWM-ORD
3h 06mnonstop
11:59 am - 3:21 pmORD-PWM
2h 22mnonstop
$374United Airlines
Find Deal
Thu, Feb 20 - Fri, Feb 28
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
$409United Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:40 pm - 9:15 pmPWM-MDW
2h 35mnonstop
9:20 am - 12:35 pmMDW-PWM
2h 15mnonstop
$502Southwest
Find Deal
Fri, Jun 6 - Thu, Jun 12

Delta flights from Portland, Maine to Chicago

Our best Delta deals on Portland, Maine to Chicago flight tickets
Delta
Jan 18
PWM4:46 pmPortland
5h 29m
1 stop
ORD9:15 pmChicago O'Hare Intl
Jan 21
ORD12:15 pmChicago O'Hare Intl
10h 36m
2 stops
PWM11:51 pmPortland
Delta
Jan 18
PWM6:00 amPortland
8h 28m
2 stops
ORD1:28 pmChicago O'Hare Intl
Jan 25
ORD6:15 amChicago O'Hare Intl
8h 51m
2 stops
PWM4:06 pmPortland
Delta
Jan 7
PWM5:23 amPortland
5h 32m
1 stop
ORD9:55 amChicago O'Hare Intl
Jan 9
ORD11:50 amChicago O'Hare Intl
11h 01m
2 stops
PWM11:51 pmPortland

United Airlines flights from Portland, Maine to Chicago

Our best United Airlines deals on Portland, Maine to Chicago flight tickets
United Airlines
Jan 18
PWM4:10 pmPortland
3h 14m
ORD6:24 pmChicago O'Hare Intl
Jan 25
ORD11:10 amChicago O'Hare Intl
2h 32m
PWM2:42 pmPortland
United Airlines
Feb 19
PWM6:01 amPortland
5h 45m
1 stop
ORD10:46 amChicago O'Hare Intl
Feb 26
ORD11:10 amChicago O'Hare Intl
2h 22m
PWM2:32 pmPortland
United Airlines
Jan 18
PWM1:38 pmPortland
6h 17m
1 stop
ORD6:55 pmChicago O'Hare Intl
Jan 25
ORD4:08 pmChicago O'Hare Intl
5h 22m
1 stop
PWM10:30 pmPortland

See travel insights to Chicago from

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 typical price of a round-trip flight between Portland, Maine and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Portland, Maine, with most prices found around $289. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Portland, Maine to Chicago during August average around $310.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Portland, Maine to Chicago for around $441.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Portland, Maine to Chicago during this time can be as low as $128. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $361.

What is the cheapest Portland to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Portland, Maine is 57 days out, which is when prices tend to be around $395. 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 flights?

There are 4 cabin classes available to choose from on Portland 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 73% 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 December 2024, prices for Portland, Maine to Chicago flights are approximately 29% more expensive 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 35m

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 $192.
The fastest flight from Portland, Maine to Chicago takes 2h 35m
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 35m, 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
3,472 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $201Free CancellationRating
8.0
8,594 reviews
Search Delta flights
United AirlinesPriceFrom $206Free CancellationRating
7.4
9,028 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.1
4,804 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 12 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 $409. 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago