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Cheap flights from Portland, Maine to Chicago 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 Portland, Maine to Chicago departing on 1/13. 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

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Find the cheapest flights from Portland, Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:46 pm - 11:35 pm
PWM
-
ORD
5h 49m1 stop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$255United Airlines
Fri, Jan 2 - Wed, Jan 7
JetBlue Logo
6:00 am - 7:26 pm
PWM
-
ORD
14h 26m2 stops
JetBlue Logo
3:15 pm - 11:36 pm
ORD
-
PWM
7h 21m1 stop
$259JetBlue
Wed, May 6 - Tue, May 12
American Airlines Logo
5:30 pm - 7:20 pm
PWM
-
ORD
2h 50mnonstop
American Airlines Logo
6:45 am - 12:00 pm
ORD
-
PWM
4h 15m1 stop
$264American Airlines
Fri, May 8 - Mon, May 11
United Airlines Logo
6:46 pm - 11:35 pm
PWM
-
ORD
5h 49m1 stop
United Airlines Logo
6:00 am - 2:31 pm
ORD
-
PWM
7h 31m1 stop
$265United Airlines
Fri, Jan 2 - Wed, Jan 7
American Airlines Logo
12:09 pm - 5:52 pm
PWM
-
ORD
6h 43m1 stop
American Airlines Logo
1:30 pm - 10:25 pm
ORD
-
PWM
7h 55m1 stop
$269American Airlines
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
5:45 am - 11:35 am
PWM
-
MDW
6h 50m1 stop
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
$269Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
5:45 am - 1:55 pm
PWM
-
MDW
9h 10m2 stops
Southwest Logo
6:50 am - 12:10 pm
MDW
-
PWM
4h 20m1 stop
$274Southwest
Wed, Jan 7 - Wed, Jan 14
Delta Logo
5:30 am - 1:16 pm
PWM
-
ORD
8h 46m2 stops
Delta Logo
7:10 am - 12:00 pm
ORD
-
PWM
3h 50m1 stop
$274Delta
Tue, Apr 7 - Sun, Apr 12
United Airlines Logo
3:05 pm - 7:53 pm
PWM
-
ORD
5h 48m1 stop
United Airlines Logo
11:48 am - 3:14 pm
ORD
-
PWM
2h 26mnonstop
$278United Airlines
Sat, Feb 14 - Tue, Feb 17
Delta Logo
5:30 am - 1:40 pm
PWM
-
ORD
9h 10m1 stop
Delta Logo
6:25 pm - 12:26 am
ORD
-
PWM
5h 01m1 stop
$279Delta
Sun, Jan 11 - Tue, Jan 13

United Airlines flights from Portland, Maine to Chicago

Our best United Airlines deals on Portland, Maine to Chicago flight tickets
United Airlines
Jan 2
PWM6:46 pmPortland
5h 49m
1 stop
ORD11:35 pmChicago O'Hare Intl
Jan 7
ORD11:00 amChicago O'Hare Intl
2h 39m
PWM2:39 pmPortland
$255
Find similar
United Airlines
Mar 6
PWM6:00 amPortland
5h 51m
1 stop
ORD10:51 amChicago O'Hare Intl
Mar 12
ORD11:48 amChicago O'Hare Intl
2h 26m
PWM3:14 pmPortland
$263
Find similar
United Airlines
Jan 2
PWM6:46 pmPortland
5h 49m
1 stop
ORD11:35 pmChicago O'Hare Intl
Jan 7
ORD6:00 amChicago O'Hare Intl
7h 31m
1 stop
PWM2:31 pmPortland
$265
Find similar

American Airlines flights from Portland, Maine to Chicago

Our best American Airlines deals on Portland, Maine to Chicago flight tickets
American Airlines
May 8
PWM5:30 pmPortland
2h 50m
ORD7:20 pmChicago O'Hare Intl
May 11
ORD6:45 amChicago O'Hare Intl
4h 15m
1 stop
PWM12:00 pmPortland
$264
Find similar
American Airlines
Apr 9
PWM12:09 pmPortland
6h 43m
1 stop
ORD5:52 pmChicago O'Hare Intl
Apr 13
ORD1:30 pmChicago O'Hare Intl
7h 55m
1 stop
PWM10:25 pmPortland
$269
Find similar
American Airlines
Jun 12
PWM7:30 pmPortland
3h 08m
ORD9:38 pmChicago O'Hare Intl
Jun 15
ORD6:30 pmChicago O'Hare Intl
2h 31m
PWM10:01 pmPortland
$300
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Chicago 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 December 18, 2025.
Use the filters below to find and compare flights from Portland, Maine to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

6:46 pm-11:35 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 1/7

11:00 am-2:39 pm

Nonstop2h 39m

$255

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 5/6

6:00 am-7:26 pm

2 stops14h 26m

Chicago O'Hare Intl

Tue 5/12

3:15 pm-11:36 pm

1 stop7h 21m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/8

5:30 pm-7:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 5/11

6:45 am-12:00 pm

1 stop4h 15m

$264

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

6:46 pm-11:35 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 1/7

6:00 am-2:31 pm

1 stop7h 31m

$265

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/9

12:09 pm-5:52 pm

1 stop6h 43m

Chicago O'Hare Intl

Mon 4/13

1:30 pm-10:25 pm

1 stop7h 55m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/7

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Wed 1/14

6:50 am-12:10 pm

1 stop4h 20m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 1/7

5:45 am-1:55 pm

2 stops9h 10m

Chicago Midway

Wed 1/14

6:50 am-12:10 pm

1 stop4h 20m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

5:30 am-1:16 pm

2 stops8h 46m

Chicago O'Hare Intl

Sun 4/12

7:10 am-12:00 pm

1 stop3h 50m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/14

3:05 pm-7:53 pm

1 stop5h 48m

Chicago O'Hare Intl

Tue 2/17

11:48 am-3:14 pm

Nonstop2h 26m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 1/11

5:30 am-1:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Tue 1/13

6:25 pm-12:26 am

1 stop5h 01m

$279

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

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 typical price of a round-trip flight between Portland, Maine and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Portland, Maine, with most prices found around $279. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Portland, Maine to Chicago during May average around $309.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $316. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland, Maine to Chicago for around $420.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Portland, Maine to Chicago during this time can be as low as $271. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $352.

What is the cheapest Portland to Chicago flight route?

Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $366 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland, Maine for as low as $234 on momondo.

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

There are 4 cabin classes available to choose from on Portland to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Chicago.

How have Portland, Maine to Chicago flight prices changed over time?

As of December 2025, prices for Portland, Maine to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.

When to book flights from Portland, Maine to Chicago

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

Cheap Portland, Maine to Chicago (PWM to CHI) flight deals and tips

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

Best Price Found

$298

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $298. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours is $400.
The fastest flight from Portland, Maine to Chicago takes 2h 35m
Direct flights go from Portland, Maine to Chicago every day.
There are 3 airports in Chicago. From Portland, Maine there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • How far is Portland to Chicago by plane?

    There are 887.4 mi between Portland and Chicago. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Portland Airport to Chicago are updated daily.

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

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

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago 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. 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?

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

Best airlines flying from Portland, Maine to Chicago

Compare and see reviews for airlines that fly from Portland, Maine to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $124Free CancellationRating
7.9
8,005 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $234Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
SouthwestPriceFrom $246Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

  • United Airlines Flights From Portland, Maine to Chicago

    United Airlines is one of the most popular airlines flying from Portland, Maine to Chicago, operating 13 flights/week on average for this route. A good United Airlines flight deal for Portland, Maine to Chicago starts from $234 round-trip, up to an average price of $375. Our users have rated United Airlines at 7.4/10.

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
Valparaiso
Schererville
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?

Yes. All flights to Chicago from Portland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Portland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

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

An easier way to manage your Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport