Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 5/19. 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.
American Airlines Logo
6:01 pm - 8:14 pm
PWM
-
ORD
3h 13mnonstop
American Airlines Logo
7:49 pm - 11:27 pm
ORD
-
PWM
2h 38mnonstop
$209American Airlines
Tue, Apr 7 - Sun, Apr 12
American Airlines Logo
5:29 am - 10:57 am
PWM
-
ORD
6h 28m
1 stop
American Airlines Logo
8:02 pm - 11:34 pm
ORD
-
PWM
2h 32mnonstop
$214American Airlines
Sat, Mar 21 - Sat, Mar 28
JetBlue Logo
2:18 pm - 10:57 pm
PWM
-
ORD
9h 39m
1 stop
JetBlue Logo
6:00 am - 1:23 pm
ORD
-
PWM
6h 23m
1 stop
$218JetBlue
Sat, May 23 - Mon, May 25
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
3:53 pm - 11:51 pm
ORD
-
PWM
6h 58m
1 stop
$219United Airlines
Fri, May 22 - Fri, Jun 5
United Airlines Logo
6:00 am - 10:51 am
PWM
-
ORD
5h 51m
1 stop
United Airlines Logo
5:47 pm - 9:04 pm
ORD
-
PWM
2h 17mnonstop
$223United Airlines
Thu, Mar 26 - Sat, Mar 28
Delta Logo
12:52 pm - 6:13 pm
PWM
-
ORD
6h 21m
1 stop
Delta Logo
7:00 am - 11:57 am
ORD
-
PWM
3h 57m
1 stop
$229Delta
Fri, May 22 - Mon, May 25
American Airlines Logo
6:01 am - 12:58 pm
PWM
-
ORD
7h 57m
1 stop
American Airlines Logo
7:49 pm - 11:27 pm
ORD
-
PWM
2h 38mnonstop
$230American Airlines
Tue, Apr 7 - Sun, Apr 12
American Airlines Logo
6:17 am - 8:34 am
PWM
-
ORD
3h 17mnonstop
American Airlines Logo
8:02 pm - 11:34 pm
ORD
-
PWM
2h 32mnonstop
$231American Airlines
Wed, Mar 25 - Wed, Mar 25
Delta Logo
12:52 pm - 6:13 pm
PWM
-
ORD
6h 21m
1 stop
Delta Logo
1:44 pm - 12:34 am
ORD
-
PWM
9h 50m
2 stops
$234Delta
Thu, May 21 - Sat, Jun 6
United Airlines Logo
6:25 pm - 8:34 pm
PWM
-
ORD
3h 09mnonstop
United Airlines Logo
6:18 pm - 9:51 pm
ORD
-
PWM
2h 33mnonstop
$237United Airlines
Wed, Jul 8 - Sun, Jul 12

American Airlines flights from Portland, Maine to Chicago O'Hare Intl Airport

Our best American Airlines deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
American Airlines
Apr 7
PWM6:01 pmPortland
3h 13m
ORD8:14 pmChicago O'Hare Intl
Apr 12
ORD7:49 pmChicago O'Hare Intl
2h 38m
PWM11:27 pmPortland
$209
American Airlines
Mar 21
PWM5:29 amPortland
6h 28m
1 stop
ORD10:57 amChicago O'Hare Intl
Mar 28
ORD8:02 pmChicago O'Hare Intl
2h 32m
PWM11:34 pmPortland
$214
American Airlines
Apr 7
PWM6:01 amPortland
7h 57m
1 stop
ORD12:58 pmChicago O'Hare Intl
Apr 12
ORD7:49 pmChicago O'Hare Intl
2h 38m
PWM11:27 pmPortland
$230

United Airlines flights from Portland, Maine to Chicago O'Hare Intl Airport

Our best United Airlines deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 22
PWM6:00 amPortland
3h 00m
ORD8:00 amChicago O'Hare Intl
Jun 5
ORD3:53 pmChicago O'Hare Intl
6h 58m
1 stop
PWM11:51 pmPortland
$219
United Airlines
Mar 26
PWM6:00 amPortland
5h 51m
1 stop
ORD10:51 amChicago O'Hare Intl
Mar 28
ORD5:47 pmChicago O'Hare Intl
2h 17m
PWM9:04 pmPortland
$223
United Airlines
Jul 8
PWM6:25 pmPortland
3h 09m
ORD8:34 pmChicago O'Hare Intl
Jul 12
ORD6:18 pmChicago O'Hare Intl
2h 33m
PWM9:51 pmPortland
$237

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Chicago O'Hare Intl 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 23, 2026.
Use the filters below to find and compare flights from Portland, Maine to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

6:01 pm-8:14 pm

Nonstop3h 13m

Chicago O'Hare Intl

Sun 4/12

7:49 pm-11:27 pm

Nonstop2h 38m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 3/21

5:29 am-10:57 am

1 stop6h 28m

Chicago O'Hare Intl

Sat 3/28

8:02 pm-11:34 pm

Nonstop2h 32m

$214

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/23

2:18 pm-10:57 pm

1 stop9h 39m

Chicago O'Hare Intl

Mon 5/25

6:00 am-1:23 pm

1 stop6h 23m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Fri 6/5

3:53 pm-11:51 pm

1 stop6h 58m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 3/26

6:00 am-10:51 am

1 stop5h 51m

Chicago O'Hare Intl

Sat 3/28

5:47 pm-9:04 pm

Nonstop2h 17m

$223

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

12:52 pm-6:13 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 5/25

7:00 am-11:57 am

1 stop3h 57m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

6:01 am-12:58 pm

1 stop7h 57m

Chicago O'Hare Intl

Sun 4/12

7:49 pm-11:27 pm

Nonstop2h 38m

$230

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 3/25

6:17 am-8:34 am

Nonstop3h 17m

Chicago O'Hare Intl

Wed 3/25

8:02 pm-11:34 pm

Nonstop2h 32m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/21

12:52 pm-6:13 pm

1 stop6h 21m

Chicago O'Hare Intl

Sat 6/6

1:44 pm-12:34 am

2 stops9h 50m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/8

6:25 pm-8:34 pm

Nonstop3h 09m

Chicago O'Hare Intl

Sun 7/12

6:18 pm-9:51 pm

Nonstop2h 33m

$237

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 O'Hare Intl 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 month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $291.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $311. This is often the case because there is less demand to fly during this day of the week. 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 $404.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Portland, Maine in the evening is the least expensive time of day to depart. momondo users have found prices as low as $274 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $383. 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 O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $352 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland, Maine for as low as $233 on momondo.

What cabin class options are available on Portland to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Portland, Maine to Chicago O'Hare Intl Airport flight prices changed over time?

As of February 2026, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 10% more expensive when compared to flights at the same time last year.

When to book flights from Portland, Maine to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to Chicago O'Hare Intl 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 O'Hare Intl Airport (PWM to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago O'Hare Intl Airport

Best Price Found

$178

Fastest flight time

2h 56m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland, Maine in the past 72 hours is $178. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $348.
The fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 56m
Direct flights go from Portland, Maine to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Portland to Chicago O'Hare Intl by plane?

    There are 899.6 mi between Portland and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 56m.

  • When did momondo last update prices for flights from Portland Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Portland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Portland Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Portland Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl 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 Portland, Maine to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Portland, Maine to Chicago O'Hare Intl Airport?

Best airlines flying from Portland, Maine to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Portland, Maine to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $114Free CancellationRating
7.9
8,236 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,339 reviews
Search American Airlines flights
United AirlinesPriceFrom $223Free CancellationRating
7.4
9,342 reviews
Search United Airlines flights

  • United Airlines Flights From Portland, Maine to Chicago O'Hare Intl Airport

    United Airlines flies from Portland, Maine to Chicago O'Hare Intl Airport around 14 times per week, with 9,342 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Portland, Maine to Chicago O'Hare Intl Airport in the last 72 hours was $223 (round-trip), much lower than the average airfare cost of $370 for United Airlines flights on this route.

  • American Airlines Flights From Portland, Maine to Chicago O'Hare Intl Airport

    American Airlines is also a popular choice for this route. American Airlines flight deals for Portland, Maine to Chicago O'Hare Intl Airport start from as low as $209 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $305. American Airlines operates 7 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.2/10 across 11,339 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Kenosha
Oak Brook
Orland Park
Joliet
Racine
Hammond
Janesville
Aurora
Elgin
Tinley Park
South Holland

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Chicago for you.

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

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

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?

Yes momondo offers price alerts on flights to Chicago from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago O'Hare Intl 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
Wed 3/25
Wed 4/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago