Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Portland, Maine to Chicago from $99

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 5/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Portland, Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
Delta Logo
12:52 pm - 12:46 am
MDW
-
PWM
10h 54m
2 stops
$218Delta
Sat, May 2 - Wed, May 6
Delta Logo
12:46 pm - 10:28 pm
PWM
-
MDW
10h 42m
2 stops
Delta Logo
12:52 pm - 12:46 am
MDW
-
PWM
10h 54m
2 stops
$223Delta
Sat, May 2 - Wed, May 6
Delta Logo
12:51 pm - 5:54 pm
PWM
-
MDW
6h 03m
1 stop
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
$229Delta
Wed, Apr 8 - Sun, Apr 12
Delta Logo
6:03 am - 12:29 pm
PWM
-
MDW
7h 26m
2 stops
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
$234Delta
Tue, Apr 7 - Sun, Apr 12
Delta Logo
6:03 am - 12:29 pm
PWM
-
MDW
7h 26m
2 stops
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
$245Delta
Tue, Apr 7 - Sun, Apr 12
Southwest Logo
12:30 pm - 4:00 pm
PWM
-
MDW
4h 30m
1 stop
Southwest Logo
6:30 am - 11:55 am
MDW
-
PWM
4h 25m
1 stop
$249Southwest
Tue, Mar 17 - Wed, Mar 25
Southwest Logo
12:30 pm - 7:30 pm
PWM
-
MDW
8h 00m
2 stops
Southwest Logo
6:30 am - 11:55 am
MDW
-
PWM
4h 25m
1 stop
$254Southwest
Tue, Mar 17 - Wed, Mar 25
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
Delta Logo
9:27 am - 3:57 pm
MDW
-
PWM
5h 30m
1 stop
$258Delta
Sat, May 2 - Wed, May 6
Southwest Logo
1:00 pm - 9:55 pm
PWM
-
MDW
9h 55m
1 stop
Southwest Logo
7:15 am - 2:30 pm
MDW
-
PWM
6h 15m
1 stop
$273Southwest
Fri, Jun 12 - Mon, Jun 15
Delta Logo
12:51 pm - 5:54 pm
PWM
-
MDW
6h 03m
1 stop
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
$274Delta
Tue, Apr 7 - Sun, Apr 12

Delta flights from Portland, Maine to Chicago Midway Airport

Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta
May 2
PWM12:46 pmPortland
6h 12m
1 stop
MDW5:58 pmChicago Midway
May 6
MDW12:52 pmChicago Midway
10h 54m
2 stops
PWM12:46 amPortland
$218
Delta
May 2
PWM12:46 pmPortland
10h 42m
2 stops
MDW10:28 pmChicago Midway
May 6
MDW12:52 pmChicago Midway
10h 54m
2 stops
PWM12:46 amPortland
$223
Delta
Apr 8
PWM12:51 pmPortland
6h 03m
1 stop
MDW5:54 pmChicago Midway
Apr 12
MDW9:35 amChicago Midway
5h 31m
1 stop
PWM4:06 pmPortland
$229

Southwest flights from Portland, Maine to Chicago Midway Airport

Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Southwest
Mar 17
PWM12:30 pmPortland
4h 30m
1 stop
MDW4:00 pmChicago Midway
Mar 25
MDW6:30 amChicago Midway
4h 25m
1 stop
PWM11:55 amPortland
$249
Southwest
Mar 17
PWM12:30 pmPortland
8h 00m
2 stops
MDW7:30 pmChicago Midway
Mar 25
MDW6:30 amChicago Midway
4h 25m
1 stop
PWM11:55 amPortland
$254
Southwest
Jun 12
PWM1:00 pmPortland
9h 55m
1 stop
MDW9:55 pmChicago Midway
Jun 15
MDW7:15 amChicago Midway
6h 15m
1 stop
PWM2:30 pmPortland
$273

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 February 15, 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

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 5/2

12:46 pm-5:58 pm

1 stop6h 12m

Chicago Midway

Wed 5/6

12:52 pm-12:46 am

2 stops10h 54m

$218

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 5/2

12:46 pm-10:28 pm

2 stops10h 42m

Chicago Midway

Wed 5/6

12:52 pm-12:46 am

2 stops10h 54m

$223

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/8

12:51 pm-5:54 pm

1 stop6h 03m

Chicago Midway

Sun 4/12

9:35 am-4:06 pm

1 stop5h 31m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 4/7

6:03 am-12:29 pm

2 stops7h 26m

Chicago Midway

Sun 4/12

9:35 am-4:06 pm

1 stop5h 31m

$234

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 4/7

6:03 am-12:29 pm

2 stops7h 26m

Chicago Midway

Sun 4/12

9:35 am-4:06 pm

1 stop5h 31m

$245

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 3/17

12:30 pm-4:00 pm

1 stop4h 30m

Chicago Midway

Wed 3/25

6:30 am-11:55 am

1 stop4h 25m

$249

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 3/17

12:30 pm-7:30 pm

2 stops8h 00m

Chicago Midway

Wed 3/25

6:30 am-11:55 am

1 stop4h 25m

$254

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 5/2

12:46 pm-5:58 pm

1 stop6h 12m

Chicago Midway

Wed 5/6

9:27 am-3:57 pm

1 stop5h 30m

$258

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 6/12

1:00 pm-9:55 pm

1 stop9h 55m

Chicago Midway

Mon 6/15

7:15 am-2:30 pm

1 stop6h 15m

$273

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 4/7

12:51 pm-5:54 pm

1 stop6h 03m

Chicago Midway

Sun 4/12

9:35 am-4:06 pm

1 stop5h 31m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, Saturday 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 $552.

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 $413 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 62% 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

$482

Fastest flight time

2h 35m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The best flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $482
The fastest flight from Portland, Maine to Chicago Midway Airport takes 2h 35m
Direct flights go from Portland, Maine to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
SouthwestPriceFrom $246Free CancellationRating
8.0
4,285 reviews
Search Southwest flights
DeltaPriceFrom $262Free CancellationRating
7.9
8,204 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
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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 3/17
Tue 3/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago