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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 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Delta Logo
12:48 pm - 6:08 pmPWM-MDW
6h 20m1 stop
Delta Logo
6:00 am - 12:30 pmMDW-PWM
5h 30m1 stop
$269Delta
Find Deal
Sat, Nov 15 - Sun, Nov 16
Southwest Logo
5:30 am - 10:10 amPWM-MDW
5h 40m1 stop
Southwest Logo
12:55 pm - 10:15 pmMDW-PWM
8h 20m1 stop
$274Southwest
Find Deal
Wed, Nov 19 - Wed, Nov 19
Southwest Logo
5:30 am - 1:00 pmPWM-MDW
8h 30m2 stops
Southwest Logo
2:30 pm - 10:15 pmMDW-PWM
6h 45m2 stops
$279Southwest
Find Deal
Wed, Nov 19 - Wed, Nov 19
Southwest Logo
5:30 am - 1:00 pmPWM-MDW
8h 30m2 stops
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$284Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
11:50 am - 3:50 pmPWM-MDW
5h 00m1 stop
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$299Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Southwest Logo
3:00 pm - 8:30 pmPWM-MDW
6h 30m2 stops
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$304Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
5:31 am - 12:01 pmPWM-MDW
7h 30m1 stop
Delta Logo
1:28 pm - 11:22 pmMDW-PWM
8h 54m2 stops
$309Delta
Find Deal
Thu, Feb 26 - Mon, Mar 2
Delta Logo
2:34 pm - 11:47 pmPWM-MDW
10h 13m2 stops
Delta Logo
1:14 pm - 10:23 pmMDW-PWM
8h 09m2 stops
$314Delta
Find Deal
Thu, Dec 4 - Sat, Dec 6
Multiple Airlines Logo
9:46 am - 10:10 pmPWM-MDW
13h 24m1 stop
Multiple Airlines Logo
1:56 pm - 5:38 pmMDW-PWM
26h 42m2 stops
$320Multiple Airlines
Find Deal
Fri, Nov 14 - Tue, Nov 18
Delta Logo
6:00 am - 11:52 amPWM-MDW
6h 52m1 stop
Delta Logo
9:32 am - 4:07 pmMDW-PWM
5h 35m1 stop
$324Delta
Find Deal
Tue, Nov 18 - Sat, Nov 22

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Nov 15
PWM12:40 pmPortland
6h 50m
1 stop
MDW6:30 pmChicago Midway
Nov 16
MDW5:05 amChicago Midway
5h 05m
1 stop
PWM11:10 amPortland
$269
Find similar
Southwest
Nov 19
PWM5:30 amPortland
5h 40m
1 stop
MDW10:10 amChicago Midway
Nov 19
MDW12:55 pmChicago Midway
8h 20m
1 stop
PWM10:15 pmPortland
$274
Find similar
Southwest
Nov 19
PWM5:30 amPortland
8h 30m
2 stops
MDW1:00 pmChicago Midway
Nov 19
MDW2:30 pmChicago Midway
6h 45m
2 stops
PWM10:15 pmPortland
$279
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
Nov 15
PWM12:48 pmPortland
6h 20m
1 stop
MDW6:08 pmChicago Midway
Nov 16
MDW6:00 amChicago Midway
5h 30m
1 stop
PWM12:30 pmPortland
$269
Find similar
Delta
Nov 15
PWM6:35 amPortland
10h 08m
2 stops
MDW3:43 pmChicago Midway
Nov 16
MDW6:00 amChicago Midway
5h 30m
1 stop
PWM12:30 pmPortland
$274
Find similar
Delta
Feb 26
PWM5:31 amPortland
7h 30m
1 stop
MDW12:01 pmChicago Midway
Mar 2
MDW1:28 pmChicago Midway
8h 54m
2 stops
PWM11:22 pmPortland
$309
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 November 3, 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

Sat 11/15

12:48 pm-6:08 pm

1 stop6h 20m

Chicago Midway

Sun 11/16

6:00 am-12:30 pm

1 stop5h 30m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/19

5:30 am-10:10 am

1 stop5h 40m

Chicago Midway

Wed 11/19

12:55 pm-10:15 pm

1 stop8h 20m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/19

5:30 am-1:00 pm

2 stops8h 30m

Chicago Midway

Wed 11/19

2:30 pm-10:15 pm

2 stops6h 45m

$279

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 12/2

5:30 am-1:00 pm

2 stops8h 30m

Chicago Midway

Tue 12/9

6:40 am-12:10 pm

1 stop4h 30m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 11/13

11:50 am-3:50 pm

1 stop5h 00m

Chicago Midway

Mon 11/17

6:40 am-12:10 pm

1 stop4h 30m

$299

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 11/13

3:00 pm-8:30 pm

2 stops6h 30m

Chicago Midway

Mon 11/17

6:40 am-12:10 pm

1 stop4h 30m

$304

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

5:31 am-12:01 pm

1 stop7h 30m

Chicago Midway

Mon 3/2

1:28 pm-11:22 pm

2 stops8h 54m

$309

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 12/4

2:34 pm-11:47 pm

2 stops10h 13m

Chicago Midway

Sat 12/6

1:14 pm-10:23 pm

2 stops8h 09m

$314

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 11/14

9:46 am-10:10 pm

1 stop13h 24m

Chicago Midway

Tue 11/18

1:56 pm-5:38 pm

2 stops26h 42m

$320

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 11/18

6:00 am-11:52 am

1 stop6h 52m

Chicago Midway

Sat 11/22

9:32 am-4:07 pm

1 stop5h 35m

$324

Flights are sorted by cheapest round-trip flights 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, Thursday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Thursday departure recently was $393. 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 $581.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $394 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $462. 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 74% 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

Direct flights

None
There are no direct flights from Portland, Maine to Chicago Midway Airport. Popular non-direct route for this connection is Portland Airport - Chicago Midway Airport.
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 4h 40m 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
8.0
4,238 reviews
Search Southwest flights
DeltaPriceFrom $253Free CancellationRating
7.9
8,002 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
Schererville
Valparaiso
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.

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