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Cheap flights from Portland, Maine to Chicago from $160

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.
Delta Logo
12:59 pm - 5:44 pmPWM  Portland-MDW Chicago Midway
5h 45m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:56 am - 9:10 pmMDW  Chicago Midway-PWM Portland
10h 14m2 stops Minneapolis St Paul New York LaGuardia
$349Delta
Fri, Dec 25 - Sat, Jan 9
Delta Logo
12:59 pm - 5:44 pmPWM  Portland-MDW Chicago Midway
5h 45m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 4:34 pmMDW  Chicago Midway-PWM Portland
9h 34m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$349Delta
Fri, Dec 25 - Tue, Jan 5
Southwest Logo
12:55 pm - 6:20 pmPWM  Portland-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
8:45 am - 2:50 pmMDW  Chicago Midway-PWM Portland
5h 05m1 stop Baltimore/Washington
$354Southwest
Wed, Jan 13 - Sun, Jan 17
Southwest Logo
12:55 pm - 6:35 pmPWM  Portland-MDW Chicago Midway
6h 40m2 stops Baltimore/Washington Greater Rochester Intl
Southwest Logo
6:35 am - 2:50 pmMDW  Chicago Midway-PWM Portland
7h 15m1 stop Baltimore/Washington
$359Southwest
Wed, Jan 13 - Sun, Jan 17
Delta Logo
12:45 pm - 6:04 pmPWM  Portland-MDW Chicago Midway
6h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:12 pm - 11:33 pmMDW  Chicago Midway-PWM Portland
5h 21m1 stop Atlanta Hartsfield-Jackson
$359Delta
Wed, Nov 18 - Wed, Dec 9
Delta Logo
6:00 am - 11:59 amPWM  Portland-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:41 pm - 11:20 pmMDW  Chicago Midway-PWM Portland
8h 39m2 stops Detroit Metropolitan Wayne County New York LaGuardia
$364Delta
Wed, Nov 18 - Wed, Dec 9
Southwest Logo
12:55 pm - 6:20 pmPWM  Portland-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
8:45 am - 2:50 pmMDW  Chicago Midway-PWM Portland
5h 05m1 stop Baltimore/Washington
$364Southwest
Wed, Jan 13 - Sun, Jan 17
Delta Logo
12:47 pm - 6:00 pmPWM  Portland-MDW Chicago Midway
6h 13m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 pm - 11:26 pmMDW  Chicago Midway-PWM Portland
5h 16m1 stop Atlanta Hartsfield-Jackson
$369Delta
Tue, Jan 12 - Sat, Jan 16
Delta Logo
12:50 pm - 6:37 pmPWM  Portland-MDW Chicago Midway
6h 47m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 4:13 pmMDW  Chicago Midway-PWM Portland
5h 43m1 stop Detroit Metropolitan Wayne County
$369Delta
Mon, Mar 22 - Thu, Mar 25
Southwest Logo
3:25 pm - 8:50 pmPWM  Portland-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
Southwest Logo
6:35 am - 12:15 pmMDW  Chicago Midway-PWM Portland
4h 40m1 stop Baltimore/Washington
$369Southwest
Wed, Jan 13 - Sun, Jan 17

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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
Dec 25
PWM12:59 pmPortland
5h 45m
1 stop
MDW5:44 pmChicago Midway
Jan 5
MDW6:00 amChicago Midway
9h 34m
2 stops
PWM4:34 pmPortland
$349
Delta
Nov 18
PWM12:45 pmPortland
6h 19m
1 stop
MDW6:04 pmChicago Midway
Dec 9
MDW5:12 pmChicago Midway
5h 21m
1 stop
PWM11:33 pmPortland
$359
Delta
Nov 18
PWM6:00 amPortland
6h 59m
1 stop
MDW11:59 amChicago Midway
Dec 9
MDW1:41 pmChicago Midway
8h 39m
2 stops
PWM11:20 pmPortland
$364

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Jan 13
PWM12:55 pmPortland
6h 25m
1 stop
MDW6:20 pmChicago Midway
Jan 17
MDW8:45 amChicago Midway
5h 05m
1 stop
PWM2:50 pmPortland
$354
Southwest
Jan 13
PWM12:55 pmPortland
6h 40m
2 stops
MDW6:35 pmChicago Midway
Jan 17
MDW6:35 amChicago Midway
7h 15m
1 stop
PWM2:50 pmPortland
$369
Southwest
Dec 2
PWM10:25 amPortland
9h 40m
2 stops
MDW7:05 pmChicago Midway
Dec 9
MDW1:15 pmChicago Midway
7h 35m
2 stops
PWM9:50 pmPortland
$379

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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Fri 12/25

12:59 pm-5:44 pm

1 stop5h 45m

Chicago Midway

Sat 1/9

9:56 am-9:10 pm

2 stops10h 14m

$349

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Fri 12/25

12:59 pm-5:44 pm

1 stop5h 45m

Chicago Midway

Tue 1/5

6:00 am-4:34 pm

2 stops9h 34m

$349

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 1/13

12:55 pm-6:20 pm

1 stop6h 25m

Chicago Midway

Sun 1/17

8:45 am-2:50 pm

1 stop5h 05m

$354

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 1/13

12:55 pm-6:35 pm

2 stops6h 40m

Chicago Midway

Sun 1/17

6:35 am-2:50 pm

1 stop7h 15m

$359

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 11/18

12:45 pm-6:04 pm

1 stop6h 19m

Chicago Midway

Wed 12/9

5:12 pm-11:33 pm

1 stop5h 21m

$359

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 11/18

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Wed 12/9

1:41 pm-11:20 pm

2 stops8h 39m

$364

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 1/13

12:55 pm-6:20 pm

1 stop6h 25m

Chicago Midway

Sun 1/17

8:45 am-2:50 pm

1 stop5h 05m

$364

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Tue 1/12

12:47 pm-6:00 pm

1 stop6h 13m

Chicago Midway

Sat 1/16

5:10 pm-11:26 pm

1 stop5h 16m

$369

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Mon 3/22

12:50 pm-6:37 pm

1 stop6h 47m

Chicago Midway

Thu 3/25

9:30 am-4:13 pm

1 stop5h 43m

$369
Quickest round-trip

PortlandChicago

PWM Portland - MDW Chicago Midway

PWMMDW

Portland

Wed 1/13

3:25 pm-8:50 pm

1 stop6h 25m

Chicago Midway

Sun 1/17

6:35 am-12:15 pm

1 stop4h 40m

$369

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $694.

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 $498 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $506. 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

$160

Fastest flight time

4h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Portland, Maine in the past 72 hours is $160. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $349.
The fastest flight from Portland, Maine to Chicago Midway Airport takes 4h 45m
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

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 4h 45m 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
4,214 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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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