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Cheap flights from Portland, Maine to Chicago from $110

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 10/31. 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

Southwest Logo
4:00 pm - 5:35 pmPWM-MDW
2h 35mnonstop
Southwest Logo
12:50 pm - 4:00 pmMDW-PWM
2h 10mnonstop
$225Southwest
Find Deal
Wed, Oct 29 - Fri, Oct 31
Southwest Logo
5:45 am - 12:00 pmPWM-MDW
7h 15m1 stop
Southwest Logo
12:50 pm - 4:00 pmMDW-PWM
2h 10mnonstop
$235Southwest
Find Deal
Wed, Oct 29 - Fri, Oct 31
Southwest Logo
5:45 am - 12:05 pmPWM-MDW
7h 20m2 stops
Southwest Logo
12:50 pm - 4:00 pmMDW-PWM
2h 10mnonstop
$240Southwest
Find Deal
Wed, Oct 29 - Fri, Oct 31
Southwest Logo
4:45 pm - 6:20 pmPWM-MDW
2h 35mnonstop
Southwest Logo
6:40 am - 12:10 pmMDW-PWM
4h 30m1 stop
$241Southwest
Find Deal
Sat, Nov 1 - Tue, Nov 4
Southwest Logo
5:25 pm - 8:50 pmPWM-MDW
4h 25m1 stop
Southwest Logo
12:50 pm - 4:00 pmMDW-PWM
2h 10mnonstop
$244Southwest
Find Deal
Tue, Oct 28 - Fri, Oct 31
Southwest Logo
5:25 pm - 8:50 pmPWM-MDW
4h 25m1 stop
Southwest Logo
4:05 pm - 9:25 pmMDW-PWM
4h 20m1 stop
$245Southwest
Find Deal
Tue, Oct 28 - Fri, Oct 31
Delta Logo
12:45 pm - 6:25 pmPWM-MDW
6h 40m1 stop
Delta Logo
1:08 pm - 12:05 amMDW-PWM
9h 57m2 stops
$259Delta
Find Deal
Tue, Oct 28 - Fri, Oct 31
Delta Logo
5:42 am - 12:28 pmPWM-MDW
7h 46m2 stops
Delta Logo
1:08 pm - 12:05 amMDW-PWM
9h 57m2 stops
$264Delta
Find Deal
Tue, Oct 28 - Fri, Oct 31
Delta Logo
12:45 pm - 6:25 pmPWM-MDW
6h 40m1 stop
Delta Logo
6:00 am - 12:30 pmMDW-PWM
5h 30m1 stop
$275Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Multiple Airlines Logo
6:18 pm - 3:58 pmPWM-MDW
22h 40m2 stops
Multiple Airlines Logo
10:13 am - 9:06 amMDW-PWM
21h 53m1 stop
$347Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Oct 29
PWM4:00 pmPortland
2h 35m
MDW5:35 pmChicago Midway
Oct 31
MDW12:50 pmChicago Midway
2h 10m
PWM4:00 pmPortland
$225
Find similar
Southwest
Oct 29
PWM5:45 amPortland
7h 15m
1 stop
MDW12:00 pmChicago Midway
Oct 31
MDW12:50 pmChicago Midway
2h 10m
PWM4:00 pmPortland
$235
Find similar
Southwest
Oct 29
PWM5:45 amPortland
7h 20m
2 stops
MDW12:05 pmChicago Midway
Oct 31
MDW12:50 pmChicago Midway
2h 10m
PWM4:00 pmPortland
$240
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
Oct 28
PWM12:45 pmPortland
6h 40m
1 stop
MDW6:25 pmChicago Midway
Oct 31
MDW1:08 pmChicago Midway
9h 57m
2 stops
PWM12:05 amPortland
$259
Find similar
Delta
Oct 28
PWM5:42 amPortland
7h 46m
2 stops
MDW12:28 pmChicago Midway
Oct 31
MDW1:08 pmChicago Midway
9h 57m
2 stops
PWM12:05 amPortland
$264
Find similar
Delta
Nov 8
PWM12:45 pmPortland
6h 40m
1 stop
MDW6:25 pmChicago Midway
Nov 11
MDW6:00 amChicago Midway
5h 30m
1 stop
PWM12:30 pmPortland
$275
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 September 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 10/29

4:00 pm-5:35 pm

Nonstop2h 35m

Chicago Midway

Fri 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$225

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 10/29

5:45 am-12:00 pm

1 stop7h 15m

Chicago Midway

Fri 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$235

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 10/29

5:45 am-12:05 pm

2 stops7h 20m

Chicago Midway

Fri 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$240

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 11/1

4:45 pm-6:20 pm

Nonstop2h 35m

Chicago Midway

Tue 11/4

6:40 am-12:10 pm

1 stop4h 30m

$241

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

5:25 pm-8:50 pm

1 stop4h 25m

Chicago Midway

Fri 10/31

12:50 pm-4:00 pm

Nonstop2h 10m

$244

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

5:25 pm-8:50 pm

1 stop4h 25m

Chicago Midway

Fri 10/31

4:05 pm-9:25 pm

1 stop4h 20m

$245

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

12:45 pm-6:25 pm

1 stop6h 40m

Chicago Midway

Fri 10/31

1:08 pm-12:05 am

2 stops9h 57m

$259

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 10/28

5:42 am-12:28 pm

2 stops7h 46m

Chicago Midway

Fri 10/31

1:08 pm-12:05 am

2 stops9h 57m

$264

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 11/8

12:45 pm-6:25 pm

1 stop6h 40m

Chicago Midway

Tue 11/11

6:00 am-12:30 pm

1 stop5h 30m

$275

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 10/1

6:18 pm-3:58 pm

2 stops22h 40m

Chicago Midway

Sun 10/5

10:13 am-9:06 am

1 stop21h 53m

$347

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, 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 $391. 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 $582.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Portland, Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing at noon. 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.

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

$203

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 $203. The best round-trip flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $393.
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 35m 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
DeltaPriceFrom $253Free CancellationRating
7.9
7,961 reviews
Search Delta flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Portland, Maine to Chicago Midway Airport

    Southwest flies from Portland, Maine to Chicago Midway Airport around 5 times per week, with 4,242 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 $264 (round-trip), much lower than the average airfare cost of $397 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
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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