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Cheap flights from Portland, Maine to Chicago from $179

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
6:30 am - 8:05 amPWM  Portland-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:40 pm - 9:55 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$337Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
5:20 am - 8:50 amPWM  Portland-MDW Chicago Midway
4h 30m1 stop Baltimore/Washington
Southwest Logo
6:40 pm - 9:55 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$347Southwest
Thu, Oct 15 - Thu, Oct 29
Southwest Logo
5:20 am - 8:50 amPWM  Portland-MDW Chicago Midway
4h 30m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 10:55 amMDW  Chicago Midway-PWM Portland
2h 10mnonstop
$347Southwest
Mon, Oct 26 - Wed, Oct 28
Southwest Logo
6:00 pm - 7:35 pmPWM  Portland-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
7:30 am - 1:05 pmMDW  Chicago Midway-PWM Portland
4h 35m1 stop Baltimore/Washington
$347Southwest
Tue, Oct 27 - Mon, Nov 2
Southwest Logo
5:20 am - 8:50 amPWM  Portland-MDW Chicago Midway
4h 30m1 stop Baltimore/Washington
Southwest Logo
7:45 am - 10:55 amMDW  Chicago Midway-PWM Portland
2h 10mnonstop
$347Southwest
Thu, Oct 15 - Tue, Oct 20
Southwest Logo
6:30 am - 8:05 amPWM  Portland-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:25 pm - 11:55 pmMDW  Chicago Midway-PWM Portland
4h 30m1 stop Baltimore/Washington
$347Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
5:40 am - 11:20 amPWM  Portland-MDW Chicago Midway
6h 40m1 stop Baltimore/Washington
Southwest Logo
4:10 pm - 7:25 pmMDW  Chicago Midway-PWM Portland
2h 15mnonstop
$347Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
6:00 pm - 7:35 pmPWM  Portland-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
12:55 pm - 11:50 pmMDW  Chicago Midway-PWM Portland
9h 55m2 stops Tampa Baltimore/Washington
$352Southwest
Tue, Oct 27 - Mon, Nov 2
Delta Logo
6:00 am - 11:59 amPWM  Portland-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 4:10 pmMDW  Chicago Midway-PWM Portland
5h 40m1 stop Detroit Metropolitan Wayne County
$357Delta
Tue, Nov 17 - Wed, Nov 18
Delta Logo
6:00 am - 11:59 amPWM  Portland-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 11:31 pmMDW  Chicago Midway-PWM Portland
5h 18m1 stop Atlanta Hartsfield-Jackson
$357Delta
Wed, Nov 18 - Sat, Nov 21

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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
Nov 14
PWM12:45 pmPortland
6h 19m
1 stop
MDW6:04 pmChicago Midway
Nov 23
MDW5:13 pmChicago Midway
5h 18m
1 stop
PWM11:31 pmPortland
$357
Delta
Nov 17
PWM12:45 pmPortland
11h 09m
2 stops
MDW10:54 pmChicago Midway
Nov 21
MDW5:13 pmChicago Midway
5h 18m
1 stop
PWM11:31 pmPortland
$372
Delta
Nov 13
PWM6:00 amPortland
6h 59m
1 stop
MDW11:59 amChicago Midway
Nov 21
MDW5:13 pmChicago Midway
5h 18m
1 stop
PWM11:31 pmPortland
$373

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Oct 1
PWM6:30 amPortland
2h 35m
MDW8:05 amChicago Midway
Oct 5
MDW6:40 pmChicago Midway
2h 15m
PWM9:55 pmPortland
$337
Southwest
Oct 15
PWM5:20 amPortland
4h 30m
1 stop
MDW8:50 amChicago Midway
Oct 29
MDW6:40 pmChicago Midway
2h 15m
PWM9:55 pmPortland
$347
Southwest
Oct 21
PWM5:40 amPortland
9h 45m
2 stops
MDW2:25 pmChicago Midway
Oct 24
MDW4:10 pmChicago Midway
2h 15m
PWM7:25 pmPortland
$352

momondo Fare Finder

 
Use the filters below to find and compare flights from Portland, Maine to Chicago Midway Airport that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip
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-9:55 pm

Nonstop2h 15m

$337

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Thu 10/15

5:20 am-8:50 am

1 stop4h 30m

Chicago Midway

Thu 10/29

6:40 pm-9:55 pm

Nonstop2h 15m

$347

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

7:45 am-10:55 am

Nonstop2h 10m

$347

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Tue 10/27

6:00 pm-7:35 pm

Nonstop2h 35m

Chicago Midway

Mon 11/2

7:30 am-1:05 pm

1 stop4h 35m

$347

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Thu 10/15

5:20 am-8:50 am

1 stop4h 30m

Chicago Midway

Tue 10/20

7:45 am-10:55 am

Nonstop2h 10m

$347

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Thu 10/1

6:30 am-8:05 am

Nonstop2h 35m

Chicago Midway

Mon 10/5

6:25 pm-11:55 pm

1 stop4h 30m

$347

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 10/21

5:40 am-11:20 am

1 stop6h 40m

Chicago Midway

Sat 10/24

4:10 pm-7:25 pm

Nonstop2h 15m

$347

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Tue 10/27

6:00 pm-7:35 pm

Nonstop2h 35m

Chicago Midway

Mon 11/2

12:55 pm-11:50 pm

2 stops9h 55m

$352

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Tue 11/17

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Wed 11/18

9:30 am-4:10 pm

1 stop5h 40m

$357

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 11/18

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Sat 11/21

5:13 pm-11:31 pm

1 stop5h 18m

$357

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 $418. 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 in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $422 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $488. 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 7% 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

$179

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 $179. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $337.
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
4,195 reviews
Search Southwest flights

  • Southwest Flights From Portland, Maine to Chicago Midway Airport

    Southwest flies from Portland, Maine to Chicago Midway Airport around 2 times per week, with 4,195 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 $374 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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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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