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Cheap flights from Portland, Maine to Chicago from $125

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 6/4. 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

Enter your travel dates to find the best prices.
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$249Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
7:40 am - 9:15 am
PWM
-
MDW
2h 35mnonstop
Southwest Logo
5:05 am - 10:55 am
MDW
-
PWM
4h 50m
1 stop
$259Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
5:20 pm - 12:40 am
PWM
-
MDW
8h 20m
2 stops
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$264Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
Southwest Logo
7:30 am - 2:10 pm
MDW
-
PWM
5h 40m
1 stop
$269Southwest
Mon, Apr 13 - Fri, Apr 17
Southwest Logo
5:20 pm - 12:40 am
PWM
-
MDW
8h 20m
2 stops
Southwest Logo
5:05 am - 10:55 am
MDW
-
PWM
4h 50m
1 stop
$274Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
2:50 pm - 10:20 pm
PWM
-
MDW
8h 30m
1 stop
Southwest Logo
7:30 am - 2:10 pm
MDW
-
PWM
5h 40m
1 stop
$275Southwest
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
3:55 pm - 7:30 pm
PWM
-
MDW
4h 35m
1 stop
Southwest Logo
5:50 pm - 11:25 pm
MDW
-
PWM
4h 35m
1 stop
$279Southwest
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
5:20 pm - 12:40 am
PWM
-
MDW
8h 20m
2 stops
Southwest Logo
2:10 pm - 9:00 pm
MDW
-
PWM
5h 50m
2 stops
$280Southwest
Thu, Jun 4 - Sat, Jun 6
Southwest Logo
5:20 pm - 1:00 am
PWM
-
MDW
8h 40m
2 stops
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$284Southwest
Fri, Jun 5 - Sun, Jun 7
Southwest Logo
5:30 am - 11:00 am
PWM
-
MDW
6h 30m
1 stop
Southwest Logo
6:15 pm - 9:30 pm
MDW
-
PWM
2h 15mnonstop
$288Southwest
Tue, Jul 14 - Wed, Jul 15

Delta flights from Portland, Maine to Chicago Midway Airport

Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta
Apr 1
PWM12:51 pmPortland
6h 03m
1 stop
MDW5:54 pmChicago Midway
Apr 3
MDW9:35 amChicago Midway
5h 31m
1 stop
PWM4:06 pmPortland
$329
Delta
Apr 3
PWM12:51 pmPortland
6h 03m
1 stop
MDW5:54 pmChicago Midway
Apr 5
MDW9:35 amChicago Midway
5h 31m
1 stop
PWM4:06 pmPortland
$344
Delta
Apr 9
PWM5:23 amPortland
7h 39m
1 stop
MDW12:02 pmChicago Midway
Apr 13
MDW9:27 amChicago Midway
5h 30m
1 stop
PWM3:57 pmPortland
$354

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Jun 4
PWM7:40 amPortland
2h 35m
MDW9:15 amChicago Midway
Jun 7
MDW7:55 pmChicago Midway
2h 15m
PWM11:10 pmPortland
$249
Southwest
Jun 4
PWM7:40 amPortland
2h 35m
MDW9:15 amChicago Midway
Jun 6
MDW1:10 pmChicago Midway
6h 50m
1 stop
PWM9:00 pmPortland
$259
Southwest
Jun 4
PWM7:40 amPortland
2h 35m
MDW9:15 amChicago Midway
Jun 6
MDW2:10 pmChicago Midway
8h 30m
2 stops
PWM11:40 pmPortland
$264

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 March 18, 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
Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/4

7:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Sun 6/7

7:55 pm-11:10 pm

Nonstop2h 15m

$249

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/4

7:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Sun 6/7

5:05 am-10:55 am

1 stop4h 50m

$259

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/4

5:20 pm-12:40 am

2 stops8h 20m

Chicago Midway

Sun 6/7

7:55 pm-11:10 pm

Nonstop2h 15m

$264

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 4/13

4:50 pm-10:20 pm

1 stop6h 30m

Chicago Midway

Fri 4/17

7:30 am-2:10 pm

1 stop5h 40m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/4

5:20 pm-12:40 am

2 stops8h 20m

Chicago Midway

Sun 6/7

5:05 am-10:55 am

1 stop4h 50m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 4/9

2:50 pm-10:20 pm

1 stop8h 30m

Chicago Midway

Thu 4/16

7:30 am-2:10 pm

1 stop5h 40m

$275

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 4/14

3:55 pm-7:30 pm

1 stop4h 35m

Chicago Midway

Thu 4/16

5:50 pm-11:25 pm

1 stop4h 35m

$279

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 6/4

5:20 pm-12:40 am

2 stops8h 20m

Chicago Midway

Sat 6/6

2:10 pm-9:00 pm

2 stops5h 50m

$280

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 6/5

5:20 pm-1:00 am

2 stops8h 40m

Chicago Midway

Sun 6/7

7:55 pm-11:10 pm

Nonstop2h 15m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 7/14

5:30 am-11:00 am

1 stop6h 30m

Chicago Midway

Wed 7/15

6:15 pm-9:30 pm

Nonstop2h 15m

$288

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, Tuesday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Tuesday departure recently was $325. 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 $454. 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?

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

$218

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 $218. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $499.
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

  • 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 $264Free CancellationRating
8.0
4,320 reviews
Search Southwest 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
Munster
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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