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Cheap flights from Portland, Maine to Chicago from $161

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
5:40 am - 10:40 am
PWM
-
MDW
6h 00m
1 stop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
$317Southwest
Sat, Sep 26 - Wed, Sep 30
Southwest Logo
7:40 am - 9:10 am
PWM
-
MDW
2h 30mnonstop
Southwest Logo
6:10 pm - 9:30 pm
MDW
-
PWM
2h 20mnonstop
$318Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
3:25 pm - 11:10 pm
PWM
-
MDW
8h 45m
2 stops
Southwest Logo
8:00 am - 4:55 pm
MDW
-
PWM
7h 55m
2 stops
$320Southwest
Fri, Oct 23 - Mon, Oct 26
Southwest Logo
5:40 am - 1:05 pm
PWM
-
MDW
8h 25m
2 stops
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
$322Southwest
Sat, Sep 26 - Wed, Sep 30
Southwest Logo
5:40 am - 10:40 am
PWM
-
MDW
6h 00m
1 stop
Southwest Logo
8:15 am - 3:00 pm
MDW
-
PWM
5h 45m
2 stops
$323Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
5:45 am - 11:50 am
PWM
-
MDW
7h 05m
2 stops
Southwest Logo
3:10 pm - 10:55 pm
MDW
-
PWM
6h 45m
1 stop
$324Southwest
Tue, Aug 25 - Sun, Aug 30
Southwest Logo
7:40 am - 9:10 am
PWM
-
MDW
2h 30mnonstop
Southwest Logo
6:10 pm - 9:30 pm
MDW
-
PWM
2h 20mnonstop
$326Southwest
Fri, Aug 28 - Sun, Aug 30
Southwest Logo
9:25 am - 4:10 pm
PWM
-
MDW
7h 45m
1 stop
Southwest Logo
3:05 pm - 10:35 pm
MDW
-
PWM
6h 30m
2 stops
$327Southwest
Sat, Oct 10 - Tue, Oct 13
Southwest Logo
10:30 am - 4:15 pm
PWM
-
MDW
6h 45m
1 stop
Southwest Logo
6:10 pm - 9:30 pm
MDW
-
PWM
2h 20mnonstop
$328Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
5:45 am - 1:05 pm
PWM
-
MDW
8h 20m
2 stops
Southwest Logo
7:55 am - 4:35 pm
MDW
-
PWM
7h 40m
2 stops
$329Southwest
Tue, Aug 25 - Sun, Aug 30

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Delta flights from Portland, Maine to Chicago Midway Airport

Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta
Sep 22
PWM6:30 amPortland
10h 46m
2 stops
MDW4:16 pmChicago Midway
Sep 30
MDW10:48 amChicago Midway
11h 29m
2 stops
PWM11:17 pmPortland
$335
Delta
Jul 14
PWM12:40 pmPortland
6h 45m
1 stop
MDW6:25 pmChicago Midway
Aug 4
MDW1:25 pmChicago Midway
9h 05m
2 stops
PWM11:30 pmPortland
$358
Delta
Sep 19
PWM6:30 amPortland
9h 55m
2 stops
MDW3:25 pmChicago Midway
Sep 21
MDW5:11 pmChicago Midway
5h 19m
1 stop
PWM11:30 pmPortland
$380

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Sep 26
PWM5:40 amPortland
6h 00m
1 stop
MDW10:40 amChicago Midway
Sep 30
MDW6:50 pmChicago Midway
2h 15m
PWM10:05 pmPortland
$317
Southwest
Sep 4
PWM7:40 amPortland
2h 30m
MDW9:10 amChicago Midway
Sep 7
MDW6:10 pmChicago Midway
2h 20m
PWM9:30 pmPortland
$318
Southwest
Oct 23
PWM3:25 pmPortland
8h 45m
2 stops
MDW11:10 pmChicago Midway
Oct 26
MDW8:00 amChicago Midway
7h 55m
2 stops
PWM4:55 pmPortland
$320

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 July 13, 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 - MDW

PWMMDW

Portland

Sat 9/26

5:40 am-10:40 am

1 stop6h 00m

Chicago Midway

Wed 9/30

6:50 pm-10:05 pm

Nonstop2h 15m

$317
Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 9/4

7:40 am-9:10 am

Nonstop2h 30m

Chicago Midway

Mon 9/7

6:10 pm-9:30 pm

Nonstop2h 20m

$318

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/23

3:25 pm-11:10 pm

2 stops8h 45m

Chicago Midway

Mon 10/26

8:00 am-4:55 pm

2 stops7h 55m

$320

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 9/26

5:40 am-1:05 pm

2 stops8h 25m

Chicago Midway

Wed 9/30

6:50 pm-10:05 pm

Nonstop2h 15m

$322

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 9/5

5:40 am-10:40 am

1 stop6h 00m

Chicago Midway

Mon 9/7

8:15 am-3:00 pm

2 stops5h 45m

$323

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 8/25

5:45 am-11:50 am

2 stops7h 05m

Chicago Midway

Sun 8/30

3:10 pm-10:55 pm

1 stop6h 45m

$324

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 8/28

7:40 am-9:10 am

Nonstop2h 30m

Chicago Midway

Sun 8/30

6:10 pm-9:30 pm

Nonstop2h 20m

$326

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 10/10

9:25 am-4:10 pm

1 stop7h 45m

Chicago Midway

Tue 10/13

3:05 pm-10:35 pm

2 stops6h 30m

$327

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 9/4

10:30 am-4:15 pm

1 stop6h 45m

Chicago Midway

Mon 9/7

6:10 pm-9:30 pm

Nonstop2h 20m

$328

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 8/25

5:45 am-1:05 pm

2 stops8h 20m

Chicago Midway

Sun 8/30

7:55 am-4:35 pm

2 stops7h 40m

$329

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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 $426. 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 $628.

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

Flying to Chicago Midway Airport from Portland, Maine in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $389 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $489. 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?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Chicago Midway Airport.

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

$233

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 $233. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $399.
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
4,249 reviews
Search Southwest flights

  • Southwest Flights From Portland, Maine to Chicago Midway Airport

    Southwest flies from Portland, Maine to Chicago Midway Airport around 5 times per week, with 4,249 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 $397 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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New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
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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