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Cheap flights from Chicago Midway Airport to Portland 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 Chicago Midway Airport to Portland departing on 6/8. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:25 pm - 11:10 pm
MDW
-
PWM
4h 45m
1 stop
Southwest Logo
4:35 pm - 8:40 pm
PWM
-
MDW
5h 05m
1 stop
$209Southwest
Sat, May 23 - Sat, May 30
Southwest Logo
6:15 pm - 9:30 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
3:55 pm - 5:40 pm
PWM
-
MDW
2h 45mnonstop
$239Southwest
Tue, Jun 9 - Sat, Jun 13
Southwest Logo
6:55 pm - 10:10 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
3:55 pm - 5:40 pm
PWM
-
MDW
2h 45mnonstop
$248Southwest
Mon, Jun 8 - Sat, Jun 13
Southwest Logo
6:55 pm - 10:10 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
6:45 am - 8:20 am
PWM
-
MDW
2h 35mnonstop
$249Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
5:50 pm - 11:25 pm
MDW
-
PWM
4h 35m
1 stop
Southwest Logo
5:30 am - 1:10 pm
PWM
-
MDW
8h 40m
2 stops
$254Southwest
Fri, May 29 - Mon, Jun 1
Southwest Logo
12:45 pm - 11:10 pm
MDW
-
PWM
9h 25m
2 stops
Southwest Logo
4:35 pm - 8:40 pm
PWM
-
MDW
5h 05m
1 stop
$258Southwest
Sat, May 23 - Sat, May 30
Southwest Logo
7:00 pm - 12:05 am
MDW
-
PWM
4h 05m
1 stop
Southwest Logo
6:45 am - 8:20 am
PWM
-
MDW
2h 35mnonstop
$259Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
2:40 pm - 12:05 am
MDW
-
PWM
8h 25m
2 stops
Southwest Logo
6:45 am - 8:20 am
PWM
-
MDW
2h 35mnonstop
$264Southwest
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
7:00 pm - 12:05 am
MDW
-
PWM
4h 05m
1 stop
Southwest Logo
1:00 pm - 9:55 pm
PWM
-
MDW
9h 55m
1 stop
$265Southwest
Thu, Jun 11 - Mon, Jun 15
Delta Logo
1:05 pm - 10:33 pm
MDW
-
PWM
8h 28m
1 stop
Delta Logo
12:50 pm - 6:31 pm
PWM
-
MDW
6h 41m
1 stop
$268Delta
Wed, Aug 26 - Fri, Sep 4

Southwest flights from Chicago Midway Airport to Portland, Maine

Our best Southwest deals on Chicago Midway Airport to Portland, Maine flight tickets
Southwest
May 23
MDW5:25 pmChicago Midway
4h 45m
1 stop
PWM11:10 pmPortland
May 30
PWM4:35 pmPortland
5h 05m
1 stop
MDW8:40 pmChicago Midway
$209
Southwest
Jun 9
MDW6:15 pmChicago Midway
2h 15m
PWM9:30 pmPortland
Jun 13
PWM3:55 pmPortland
2h 45m
MDW5:40 pmChicago Midway
$239
Southwest
Jun 8
MDW6:55 pmChicago Midway
2h 15m
PWM10:10 pmPortland
Jun 13
PWM3:55 pmPortland
2h 45m
MDW5:40 pmChicago Midway
$248

Delta flights from Chicago Midway Airport to Portland, Maine

Our best Delta deals on Chicago Midway Airport to Portland, Maine flight tickets
Delta
Aug 26
MDW1:05 pmChicago Midway
8h 28m
1 stop
PWM10:33 pmPortland
Sep 5
PWM11:38 amPortland
7h 27m
1 stop
MDW6:05 pmChicago Midway
$268
Delta
May 12
MDW12:51 pmChicago Midway
10h 52m
2 stops
PWM12:43 amPortland
May 20
PWM2:05 pmPortland
8h 04m
1 stop
MDW9:09 pmChicago Midway
$274
Delta
May 13
MDW12:51 pmChicago Midway
10h 52m
2 stops
PWM12:43 amPortland
May 19
PWM6:25 amPortland
10h 47m
2 stops
MDW4:12 pmChicago Midway
$279

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Portland, Maine 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 March 13, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 5/23

5:25 pm-11:10 pm

1 stop4h 45m

Portland

Sat 5/30

4:35 pm-8:40 pm

1 stop5h 05m

$209

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 6/9

6:15 pm-9:30 pm

Nonstop2h 15m

Portland

Sat 6/13

3:55 pm-5:40 pm

Nonstop2h 45m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 6/8

6:55 pm-10:10 pm

Nonstop2h 15m

Portland

Sat 6/13

3:55 pm-5:40 pm

Nonstop2h 45m

$248
Quickest round-trip

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/4

6:55 pm-10:10 pm

Nonstop2h 15m

Portland

Sun 6/7

6:45 am-8:20 am

Nonstop2h 35m

$249

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 5/29

5:50 pm-11:25 pm

1 stop4h 35m

Portland

Mon 6/1

5:30 am-1:10 pm

2 stops8h 40m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 5/23

12:45 pm-11:10 pm

2 stops9h 25m

Portland

Sat 5/30

4:35 pm-8:40 pm

1 stop5h 05m

$258

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/4

7:00 pm-12:05 am

1 stop4h 05m

Portland

Sun 6/7

6:45 am-8:20 am

Nonstop2h 35m

$259

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/4

2:40 pm-12:05 am

2 stops8h 25m

Portland

Sun 6/7

6:45 am-8:20 am

Nonstop2h 35m

$264

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 6/11

7:00 pm-12:05 am

1 stop4h 05m

Portland

Mon 6/15

1:00 pm-9:55 pm

1 stop9h 55m

$265

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 8/26

1:05 pm-10:33 pm

1 stop8h 28m

Portland

Fri 9/4

12:50 pm-6:31 pm

1 stop6h 41m

$268

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 Portland from

How to get the cheapest flight ticket from Chicago Midway Airport to Portland, Maine

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 Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $301. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $387.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Portland, Maine when you can find flight prices for as low as $314. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the afternoon because they tend to be around $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago Midway - Portland flight prices

What cabin class options are available on Chicago Midway to Portland flights?

There is only 1 cabin class available to choose from on Chicago Midway to Portland 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 Chicago Midway Airport to Portland, Maine flights?

You could potentially save up to 75% on your flight if you consider stops on a Chicago Midway Airport to Portland, Maine flight.

When to book flights from Chicago Midway Airport to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Portland, Maine (MDW to PWM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Portland, Maine

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Portland, Maine

1 airport
The fastest flight from Chicago Midway Airport to Portland, Maine takes 2h 15m
Direct flights go from Chicago Midway Airport to Portland, Maine every day.
There is 1 airport in Portland, Maine. From Chicago Midway Airport there are direct flights to Portland (PWM).
Search flight deals

  • How far is Chicago Midway to Portland by plane?

    The straight-line distance from Chicago Midway to Portland is 894.8 mi. By plane, this route typically takes 2h 15m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Portland Airport?

    Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Portland Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Portland 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 Chicago Midway Airport to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The necessary travel and health documents for your Portland Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Portland, Maine?

  • What is the most popular airline from Chicago Midway Airport to Portland, Maine?

Best airlines flying from Chicago Midway Airport to Portland, Maine

Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $259Free CancellationRating
8.0
4,318 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Portland, Maine

    The lowest priced Southwest flight from Chicago Midway Airport to Portland, Maine from the last 72 hours was $259. Generally, Southwest has 3 flights on this route every week with an average price of $490. Southwest is rated 8.0/10 by our users.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Oxford
Bath
Georgetown
Falmouth
Tamworth

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Portland. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

momondo does allow users to show only those flights to Portland from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Portland?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Portland from Chicago.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Portland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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