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Cheap flights from Portland, Maine to Chicago from $100

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

JetBlue Logo
2:19 pm - 10:28 pmPWM-ORD
9h 09m1 stop
JetBlue Logo
6:15 am - 1:23 pmORD-PWM
6h 08m1 stop
$183JetBlue
Find Deal
Mi, Aug 20 - So, Aug 24
JetBlue Logo
6:05 am - 11:18 amPWM-ORD
6h 13m1 stop
JetBlue Logo
6:10 am - 1:22 pmORD-PWM
6h 12m1 stop
$185JetBlue
Find Deal
Di, Aug 26 - Mi, Sep 3
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
$199American Airlines
Find Deal
Sa, Aug 30 - So, Aug 31
Southwest Logo
1:15 pm - 6:35 pmPWM-MDW
6h 20m1 stop
Southwest Logo
5:55 pm - 9:15 pmMDW-PWM
2h 20mnonstop
$209Southwest
Find Deal
Sa, Aug 30 - So, Aug 31
American Airlines Logo
12:08 pm - 2:10 pmPWM-ORD
3h 02mnonstop
American Airlines Logo
6:45 pm - 10:28 pmORD-PWM
2h 43mnonstop
$217American Airlines
Find Deal
Do, Aug 28 - Di, Sep 2
Southwest Logo
10:35 am - 12:05 pmPWM-MDW
2h 30mnonstop
Southwest Logo
11:40 am - 2:55 pmMDW-PWM
2h 15mnonstop
$217Southwest
Find Deal
Do, Aug 28 - Di, Sep 2
Delta Logo
5:30 pm - 11:56 pmPWM-ORD
7h 26m1 stop
Delta Logo
5:45 am - 12:29 pmORD-PWM
5h 44m1 stop
$219Delta
Find Deal
Sa, Aug 30 - So, Aug 31
Delta Logo
11:48 am - 8:23 pmPWM-ORD
9h 35m2 stops
Delta Logo
5:45 am - 12:29 pmORD-PWM
5h 44m1 stop
$224Delta
Find Deal
Sa, Aug 30 - So, Aug 31
United Airlines Logo
7:26 pm - 11:15 pmPWM-ORD
4h 49m1 stop
United Airlines Logo
10:58 am - 2:26 pmORD-PWM
2h 28mnonstop
$227United Airlines
Find Deal
Di, Sep 16 - Sa, Sep 20
United Airlines Logo
6:10 am - 8:05 amPWM-ORD
2h 55mnonstop
United Airlines Logo
6:30 pm - 10:01 pmORD-PWM
2h 31mnonstop
$283United Airlines
Find Deal
Mi, Aug 13 - So, Aug 17

JetBlue flights from Portland, Maine to Chicago

Our best JetBlue deals on Portland, Maine to Chicago flight tickets
JetBlue
Aug 20
PWM2:19 pmPortland
9h 09m
1 stop
ORD10:28 pmChicago O'Hare Intl
Aug 24
ORD6:15 amChicago O'Hare Intl
6h 08m
1 stop
PWM1:23 pmPortland
$183
Find similar
JetBlue
Aug 26
PWM6:05 amPortland
6h 13m
1 stop
ORD11:18 amChicago O'Hare Intl
Sep 3
ORD6:10 amChicago O'Hare Intl
6h 12m
1 stop
PWM1:22 pmPortland
$185
Find similar
JetBlue
Sep 11
PWM2:17 pmPortland
7h 32m
1 stop
ORD8:49 pmChicago O'Hare Intl
Sep 14
ORD6:45 amChicago O'Hare Intl
5h 37m
1 stop
PWM1:22 pmPortland
$201
Find similar

United Airlines flights from Portland, Maine to Chicago

Our best United Airlines deals on Portland, Maine to Chicago flight tickets
United Airlines
Sep 16
PWM7:26 pmPortland
4h 49m
1 stop
ORD11:15 pmChicago O'Hare Intl
Sep 20
ORD10:58 amChicago O'Hare Intl
2h 28m
PWM2:26 pmPortland
$227
Find similar
United Airlines
Aug 13
PWM6:10 amPortland
2h 55m
ORD8:05 amChicago O'Hare Intl
Aug 17
ORD6:30 pmChicago O'Hare Intl
2h 31m
PWM10:01 pmPortland
$283
Find similar
United Airlines
Aug 28
PWM4:56 pmPortland
2h 51m
ORD6:47 pmChicago O'Hare Intl
Sep 3
ORD4:50 pmChicago O'Hare Intl
5h 13m
1 stop
PWM11:03 pmPortland
$297
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 August 1, 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

Mi 8/20

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

So 8/24

6:15 am-1:23 pm

1 stop6h 08m

$183

PortlandChicago

PWM - ORD

PWMORD

Portland

Di 8/26

6:05 am-11:18 am

1 stop6h 13m

Chicago O'Hare Intl

Mi 9/3

6:10 am-1:22 pm

1 stop6h 12m

$185

PortlandChicago

PWM - ORD

PWMORD

Portland

Sa 8/30

6:30 am-8:32 am

Nonstop3h 02m

Chicago O'Hare Intl

So 8/31

8:13 pm-11:59 pm

Nonstop2h 46m

$199

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sa 8/30

1:15 pm-6:35 pm

1 stop6h 20m

Chicago Midway

So 8/31

5:55 pm-9:15 pm

Nonstop2h 20m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Do 8/28

12:08 pm-2:10 pm

Nonstop3h 02m

Chicago O'Hare Intl

Di 9/2

6:45 pm-10:28 pm

Nonstop2h 43m

$217

PortlandChicago

PWM - MDW

PWMMDW

Portland

Do 8/28

10:35 am-12:05 pm

Nonstop2h 30m

Chicago Midway

Di 9/2

11:40 am-2:55 pm

Nonstop2h 15m

$217

PortlandChicago

PWM - ORD

PWMORD

Portland

Sa 8/30

5:30 pm-11:56 pm

1 stop7h 26m

Chicago O'Hare Intl

So 8/31

5:45 am-12:29 pm

1 stop5h 44m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sa 8/30

11:48 am-8:23 pm

2 stops9h 35m

Chicago O'Hare Intl

So 8/31

5:45 am-12:29 pm

1 stop5h 44m

$224

PortlandChicago

PWM - ORD

PWMORD

Portland

Di 9/16

7:26 pm-11:15 pm

1 stop4h 49m

Chicago O'Hare Intl

Sa 9/20

10:58 am-2:26 pm

Nonstop2h 28m

$227

PortlandChicago

PWM - ORD

PWMORD

Portland

Mi 8/13

6:10 am-8:05 am

Nonstop2h 55m

Chicago O'Hare Intl

So 8/17

6:30 pm-10:01 pm

Nonstop2h 31m

$283

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 cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Portland, Maine, with most prices found around $283. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Portland, Maine to Chicago during September average around $283.

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 Thursday when prices can be found for as low as $446. 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 $633.

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 at noon. Flights from Portland, Maine to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $498.

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 $376 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 $228 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 August 2025, prices for Portland, Maine to Chicago flights are approximately 54% 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

$100

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $100. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours is $183.
The fastest flight from Portland, Maine to Chicago takes 2h 30m
Direct flights go from Portland, Maine to Chicago every day.
There are 2 airports near Chicago: 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 30m, 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
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $204Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $226Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Portland, Maine to Chicago

    Southwest is one of the most popular airlines flying from Portland, Maine to Chicago, operating 3 flights/week on average for this route. A good Southwest flight deal for Portland, Maine to Chicago starts from $264 round-trip, up to an average price of $390. Our users have rated Southwest at 8.0/10.

  • United Airlines Flights From Portland, Maine to Chicago

    United Airlines (7.4/10 from 8,900 reviews) operates around 14 flights from Portland, Maine to Chicago in any given week. The average United Airlines airfare for this route is around $385, with deals from around $226 rare but found on momondo. Referenced prices are for round-trip Portland, Maine to Chicago flight searches in the last 72 hours.

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
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.

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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