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Cheap flights from Portland, Maine to Chicago from $129

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 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Portland, Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:20 am - 10:00 amPWM  Portland-MDW Chicago Midway
5h 40m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 10:55 amMDW  Chicago Midway-PWM Portland
2h 10mnonstop
$240Southwest
Mon, Oct 26 - Wed, Oct 28
Southwest Logo
10:30 am - 4:40 pmPWM  Portland-MDW Chicago Midway
7h 10m1 stop Baltimore/Washington
Southwest Logo
6:30 pm - 9:45 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$245Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
10:30 am - 5:10 pmPWM  Portland-MDW Chicago Midway
7h 40m2 stops Baltimore/Washington Greater Rochester Intl
Southwest Logo
6:30 pm - 9:45 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$250Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
5:20 am - 8:50 amPWM  Portland-MDW Chicago Midway
4h 30m1 stop Baltimore/Washington
Southwest Logo
8:10 am - 3:30 pmMDW  Chicago Midway-PWM Portland
6h 20m1 stop Baltimore/Washington
$250Southwest
Mon, Oct 26 - Wed, Oct 28
Southwest Logo
7:40 am - 9:10 amPWM  Portland-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:50 pm - 10:10 pmMDW  Chicago Midway-PWM Portland
2h 20mnonstop
$251Southwest
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
12:55 pm - 7:30 pmPWM  Portland-MDW Chicago Midway
7h 35m2 stops Baltimore/Washington Greater Rochester Intl
Southwest Logo
7:30 am - 1:05 pmMDW  Chicago Midway-PWM Portland
4h 35m1 stop Baltimore/Washington
$254Southwest
Wed, Oct 28 - Mon, Nov 2
Delta Logo
6:30 am - 4:15 pmPWM  Portland-MDW Chicago Midway
10h 45m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
Delta Logo
5:11 pm - 11:28 pmMDW  Chicago Midway-PWM Portland
5h 17m1 stop Atlanta Hartsfield-Jackson
$255Delta
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
5:20 am - 8:50 amPWM  Portland-MDW Chicago Midway
4h 30m1 stop Baltimore/Washington
Southwest Logo
1:35 pm - 8:30 pmMDW  Chicago Midway-PWM Portland
5h 55m2 stops Cleveland Hopkins Intl Baltimore/Washington
$255Southwest
Mon, Oct 26 - Wed, Oct 28
Southwest Logo
6:30 am - 8:05 amPWM  Portland-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:40 pm - 9:50 pmMDW  Chicago Midway-PWM Portland
2h 10mnonstop
$257Southwest
Thu, Oct 1 - Mon, Oct 5
Delta Logo
6:25 am - 4:47 pmPWM  Portland-MDW Chicago Midway
11h 22m2 stops New York LaGuardia Minneapolis St Paul
Delta Logo
6:04 am - 1:02 pmMDW  Chicago Midway-PWM Portland
5h 58m1 stop Atlanta Hartsfield-Jackson
$258Delta
Sat, Oct 24 - Tue, Oct 27

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Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Oct 26
PWM5:20 amPortland
5h 40m
1 stop
MDW10:00 amChicago Midway
Oct 28
MDW7:45 amChicago Midway
2h 10m
PWM10:55 amPortland
$240
Southwest
Sep 5
PWM10:30 amPortland
7h 40m
2 stops
MDW5:10 pmChicago Midway
Sep 6
MDW6:30 pmChicago Midway
2h 15m
PWM9:45 pmPortland
$250
Southwest
Sep 4
PWM7:40 amPortland
2h 30m
MDW9:10 amChicago Midway
Sep 8
MDW6:50 pmChicago Midway
2h 20m
PWM10:10 pmPortland
$251

Delta flights from Portland, Maine to Chicago Midway Airport

Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta
Sep 16
PWM6:30 amPortland
10h 45m
2 stops
MDW4:15 pmChicago Midway
Sep 22
MDW5:11 pmChicago Midway
5h 17m
1 stop
PWM11:28 pmPortland
$255
Delta
Oct 24
PWM6:25 amPortland
11h 22m
2 stops
MDW4:47 pmChicago Midway
Oct 27
MDW5:15 pmChicago Midway
5h 20m
1 stop
PWM11:35 pmPortland
$258
Delta
Sep 16
PWM6:30 amPortland
10h 45m
2 stops
MDW4:15 pmChicago Midway
Sep 22
MDW1:00 pmChicago Midway
9h 56m
2 stops
PWM11:56 pmPortland
$260

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 14, 2026.
Use the filters below to find and compare flights from Portland, Maine to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Mon 10/26

5:20 am-10:00 am

1 stop5h 40m

Chicago Midway

Wed 10/28

7:45 am-10:55 am

Nonstop2h 10m

$240

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Sat 9/5

10:30 am-4:40 pm

1 stop7h 10m

Chicago Midway

Sun 9/6

6:30 pm-9:45 pm

Nonstop2h 15m

$245

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Sat 9/5

10:30 am-5:10 pm

2 stops7h 40m

Chicago Midway

Sun 9/6

6:30 pm-9:45 pm

Nonstop2h 15m

$250

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Mon 10/26

5:20 am-8:50 am

1 stop4h 30m

Chicago Midway

Wed 10/28

8:10 am-3:30 pm

1 stop6h 20m

$250

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Fri 9/4

7:40 am-9:10 am

Nonstop2h 30m

Chicago Midway

Tue 9/8

6:50 pm-10:10 pm

Nonstop2h 20m

$251

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 10/28

12:55 pm-7:30 pm

2 stops7h 35m

Chicago Midway

Mon 11/2

7:30 am-1:05 pm

1 stop4h 35m

$254

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 9/16

6:30 am-4:15 pm

2 stops10h 45m

Chicago Midway

Tue 9/22

5:11 pm-11:28 pm

1 stop5h 17m

$255

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Mon 10/26

5:20 am-8:50 am

1 stop4h 30m

Chicago Midway

Wed 10/28

1:35 pm-8:30 pm

2 stops5h 55m

$255
Quickest round-trip

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Thu 10/1

6:30 am-8:05 am

Nonstop2h 35m

Chicago Midway

Mon 10/5

6:40 pm-9:50 pm

Nonstop2h 10m

$257

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Sat 10/24

6:25 am-4:47 pm

2 stops11h 22m

Chicago Midway

Tue 10/27

6:04 am-1:02 pm

1 stop5h 58m

$258

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 Midway 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 day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Friday departure recently was $414. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $631.

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

Flying to Chicago Midway Airport from Portland, Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $487. 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 Midway flight route?

Fly from Portland to Chicago Midway for the best Portland - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Portland, Maine to Chicago Midway 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 Midway Airport flights?

You could potentially save up to 26% on your flight if you consider stops on a Portland, Maine to Chicago Midway Airport flight.

When to book flights from Portland, Maine to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to Chicago Midway 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 Midway Airport (PWM to MDW) flight deals and tips

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

Best Price Found

$260

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Portland, Maine in the past 72 hours is $260. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $366.
The fastest flight from Portland, Maine to Chicago Midway Airport takes 2h 30m
Direct flights go from Portland, Maine to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Portland, Maine to Chicago Midway Airport

  • How far is Portland to Chicago Midway by plane?

    The straight-line distance from Portland to Chicago Midway is 894.8 mi. Typically, this will take 2h 30m by plane in normal conditions.

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

    Prices for flights from Portland Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

    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 Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. 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 Midway Airport?

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

Best airlines flying from Portland, Maine to Chicago Midway Airport

Compare and see reviews for airlines that fly from Portland, Maine to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $267Free CancellationRating
8.0
4,218 reviews
Search Southwest flights

  • Southwest Flights From Portland, Maine to Chicago Midway Airport

    Southwest flies from Portland, Maine to Chicago Midway Airport around 6 times per week, with 4,218 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Portland, Maine to Chicago Midway Airport in the last 72 hours was $267 (round-trip), much lower than the average airfare cost of $378 for Southwest flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Schererville
Munster
Chesterton
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Saint John

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?

Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Chicago?

Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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