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 1/23. 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.
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$209United Airlines
Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
7:10 am - 1:56 pm
ORD
-
PWM
5h 46m1 stop
$219United Airlines
Sat, Jan 31 - Tue, Feb 3
Delta Logo
1:13 pm - 6:58 pm
PWM
-
ORD
6h 45m1 stop
Delta Logo
6:25 pm - 12:20 am
ORD
-
PWM
4h 55m1 stop
$229Delta
Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$233United Airlines
Fri, Jan 16 - Tue, Jan 20
Delta Logo
12:43 pm - 7:21 pm
PWM
-
ORD
7h 38m2 stops
Delta Logo
6:30 am - 12:00 pm
ORD
-
PWM
4h 30m1 stop
$234Delta
Tue, Feb 3 - Tue, Feb 24
Delta Logo
1:13 pm - 11:56 pm
PWM
-
ORD
11h 43m2 stops
Delta Logo
5:30 am - 5:16 pm
ORD
-
PWM
10h 46m2 stops
$239Delta
Sat, Jan 31 - Tue, Feb 3
Delta Logo
2:35 pm - 8:17 pm
PWM
-
ORD
6h 42m1 stop
Delta Logo
6:25 pm - 12:18 am
ORD
-
PWM
4h 53m1 stop
$240Delta
Sat, Feb 14 - Tue, Feb 17
Delta Logo
2:35 pm - 8:17 pm
PWM
-
ORD
6h 42m1 stop
Delta Logo
11:18 am - 11:20 pm
ORD
-
PWM
11h 02m2 stops
$245Delta
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$249United Airlines
Sat, Jan 10 - Wed, Jan 14
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
8:52 am - 2:31 pm
ORD
-
PWM
4h 39m1 stop
$250United Airlines
Fri, Jan 23 - Fri, Jan 30

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
Jan 31
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Feb 3
ORD11:00 amChicago O'Hare Intl
2h 39m
PWM2:39 pmPortland
$209
Find similar
United Airlines
Jan 31
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Feb 3
ORD7:10 amChicago O'Hare Intl
5h 46m
1 stop
PWM1:56 pmPortland
$219
Find similar
United Airlines
Jan 16
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Jan 20
ORD11:00 amChicago O'Hare Intl
2h 39m
PWM2:39 pmPortland
$233
Find similar

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

Our best Delta deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
Delta
Jan 31
PWM1:13 pmPortland
6h 45m
1 stop
ORD6:58 pmChicago O'Hare Intl
Feb 3
ORD6:25 pmChicago O'Hare Intl
4h 55m
1 stop
PWM12:20 amPortland
$229
Find similar
Delta
Feb 3
PWM12:43 pmPortland
7h 38m
2 stops
ORD7:21 pmChicago O'Hare Intl
Feb 24
ORD6:30 amChicago O'Hare Intl
4h 30m
1 stop
PWM12:00 pmPortland
$234
Find similar
Delta
Jan 31
PWM1:13 pmPortland
11h 43m
2 stops
ORD11:56 pmChicago O'Hare Intl
Feb 3
ORD5:30 amChicago O'Hare Intl
10h 46m
2 stops
PWM5:16 pmPortland
$239
Find similar

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 December 28, 2025.
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

Sat 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

7:10 am-1:56 pm

1 stop5h 46m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

1:13 pm-6:58 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 2/3

6:25 pm-12:20 am

1 stop4h 55m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/16

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/20

11:00 am-2:39 pm

Nonstop2h 39m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/3

12:43 pm-7:21 pm

2 stops7h 38m

Chicago O'Hare Intl

Tue 2/24

6:30 am-12:00 pm

1 stop4h 30m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

1:13 pm-11:56 pm

2 stops11h 43m

Chicago O'Hare Intl

Tue 2/3

5:30 am-5:16 pm

2 stops10h 46m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/14

2:35 pm-8:17 pm

1 stop6h 42m

Chicago O'Hare Intl

Tue 2/17

6:25 pm-12:18 am

1 stop4h 53m

$240

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/14

2:35 pm-8:17 pm

1 stop6h 42m

Chicago O'Hare Intl

Tue 2/17

11:18 am-11:20 pm

2 stops11h 02m

$245

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/10

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 1/14

11:00 am-2:39 pm

Nonstop2h 39m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/23

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/30

8:52 am-2:31 pm

1 stop4h 39m

$250

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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $302.

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 Thursday when prices can be found for as low as $428. 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 $616.

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 $218 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $480. 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 $365 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 $234 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.

Can stopping save me money on Portland, Maine to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Chicago O'Hare Intl Airport.

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

As of December 2025, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 12% cheaper 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

$263

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 $263. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $398.
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 $124Free CancellationRating
7.9
8,019 reviews
Search Delta flights
American AirlinesPriceFrom $208Free CancellationRating
7.2
11,072 reviews
Search American Airlines flights
United AirlinesPriceFrom $235Free CancellationRating
7.4
9,113 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 13 times per week, with 9,113 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 $235 (round-trip), much lower than the average airfare cost of $375 for United Airlines flights on this route.

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
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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
Tue 1/27
Tue 2/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago