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Cheap flights from Portland, Maine to Chicago from $115

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 3/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland, Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:45 am - 11:35 am
PWM
-
MDW
6h 50m1 stop
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
$269Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
5:45 am - 1:55 pm
PWM
-
MDW
9h 10m2 stops
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
$274Southwest
Wed, Jan 7 - Wed, Jan 14
Delta Logo
12:50 pm - 6:31 pm
PWM
-
MDW
6h 41m1 stop
Delta Logo
9:30 am - 4:15 pm
MDW
-
PWM
5h 45m1 stop
$279Delta
Tue, May 5 - Tue, May 12
Delta Logo
12:50 pm - 10:07 pm
PWM
-
MDW
10h 17m2 stops
Delta Logo
1:26 pm - 11:22 pm
MDW
-
PWM
8h 56m2 stops
$289Delta
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
3:55 pm - 9:25 pm
PWM
-
MDW
6h 30m1 stop
Southwest Logo
9:50 am - 2:55 pm
MDW
-
PWM
4h 05m1 stop
$294Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
5:45 am - 11:35 am
PWM
-
MDW
6h 50m1 stop
Southwest Logo
1:15 pm - 10:15 pm
MDW
-
PWM
8h 00m1 stop
$299Southwest
Fri, Jan 9 - Fri, Jan 9
Delta Logo
2:35 pm - 10:22 pm
PWM
-
MDW
8h 47m2 stops
Delta Logo
9:33 am - 7:38 pm
MDW
-
PWM
9h 05m2 stops
$300Delta
Sun, Jan 25 - Sat, Jan 31
Southwest Logo
1:00 pm - 7:35 pm
PWM
-
MDW
7h 35m2 stops
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
$316Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
5:30 am - 12:10 pm
PWM
-
MDW
7h 40m1 stop
Southwest Logo
6:35 am - 2:15 pm
MDW
-
PWM
6h 40m1 stop
$319Southwest
Fri, Mar 6 - Thu, Mar 12
Southwest Logo
5:30 am - 12:10 pm
PWM
-
MDW
7h 40m1 stop
Southwest Logo
8:00 am - 2:15 pm
MDW
-
PWM
5h 15m2 stops
$320Southwest
Fri, Mar 6 - Thu, Mar 12

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Jan 7
PWM5:45 amPortland
6h 50m
1 stop
MDW11:35 amChicago Midway
Jan 14
MDW6:50 amChicago Midway
4h 20m
1 stop
PWM12:10 pmPortland
$269
Find similar
Southwest
Jan 7
PWM5:45 amPortland
9h 10m
2 stops
MDW1:55 pmChicago Midway
Jan 14
MDW6:50 amChicago Midway
4h 20m
1 stop
PWM12:10 pmPortland
$274
Find similar
Southwest
Jan 15
PWM3:55 pmPortland
6h 30m
1 stop
MDW9:25 pmChicago Midway
Jan 18
MDW9:50 amChicago Midway
4h 05m
1 stop
PWM2:55 pmPortland
$294
Find similar

Delta flights from Portland, Maine to Chicago Midway Airport

Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta
May 5
PWM12:50 pmPortland
6h 41m
1 stop
MDW6:31 pmChicago Midway
May 12
MDW9:30 amChicago Midway
5h 45m
1 stop
PWM4:15 pmPortland
$279
Find similar
Delta
Jan 17
PWM12:50 pmPortland
10h 17m
2 stops
MDW10:07 pmChicago Midway
Jan 19
MDW1:26 pmChicago Midway
8h 56m
2 stops
PWM11:22 pmPortland
$289
Find similar
Delta
Jan 25
PWM2:35 pmPortland
8h 47m
2 stops
MDW10:22 pmChicago Midway
Jan 31
MDW9:33 amChicago Midway
9h 05m
2 stops
PWM7:38 pmPortland
$300
Find similar

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 December 17, 2025.
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

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/7

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Wed 1/14

6:50 am-12:10 pm

1 stop4h 20m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/7

5:45 am-1:55 pm

2 stops9h 10m

Chicago Midway

Wed 1/14

6:50 am-12:10 pm

1 stop4h 20m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 5/5

12:50 pm-6:31 pm

1 stop6h 41m

Chicago Midway

Tue 5/12

9:30 am-4:15 pm

1 stop5h 45m

$279

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 1/17

12:50 pm-10:07 pm

2 stops10h 17m

Chicago Midway

Mon 1/19

1:26 pm-11:22 pm

2 stops8h 56m

$289

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 1/15

3:55 pm-9:25 pm

1 stop6h 30m

Chicago Midway

Sun 1/18

9:50 am-2:55 pm

1 stop4h 05m

$294

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 1/9

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Fri 1/9

1:15 pm-10:15 pm

1 stop8h 00m

$299

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sun 1/25

2:35 pm-10:22 pm

2 stops8h 47m

Chicago Midway

Sat 1/31

9:33 am-7:38 pm

2 stops9h 05m

$300

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 1/15

1:00 pm-7:35 pm

2 stops7h 35m

Chicago Midway

Sun 1/18

6:50 am-12:10 pm

1 stop4h 20m

$316

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 3/6

5:30 am-12:10 pm

1 stop7h 40m

Chicago Midway

Thu 3/12

6:35 am-2:15 pm

1 stop6h 40m

$319

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 3/6

5:30 am-12:10 pm

1 stop7h 40m

Chicago Midway

Thu 3/12

8:00 am-2:15 pm

2 stops5h 15m

$320

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Wednesday departure recently was $281. 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 $413.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $269 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $344. 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 to Chicago Midway flights?

There is only 1 cabin class available to choose from on Portland to Chicago Midway 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 23% 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

Fastest flight time

6h 05m

Direct flights

Mon
The fastest flight from Portland, Maine to Chicago Midway Airport takes 6h 05m
Direct flights go from Portland, Maine to Chicago Midway Airport on Monday. There are no airlines offering direct flights.
Search flight deals

  • 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 6h 05m 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 $246Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
DeltaPriceFrom $253Free CancellationRating
7.9
8,008 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
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.

An easier way to manage your Chicago Midway Airport trip

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