Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 8/21. 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

JetBlue Logo
7:30 am - 12:10 pmPWM-ORD
5h 40m1 stop
JetBlue Logo
6:45 am - 1:22 pmORD-PWM
5h 37m1 stop
$183JetBlue
Find Deal
Thu, Oct 2 - Sun, Oct 5
JetBlue Logo
7:09 am - 12:10 pmPWM-ORD
6h 01m1 stop
JetBlue Logo
1:36 pm - 10:02 pmORD-PWM
7h 26m1 stop
$193JetBlue
Find Deal
Tue, Sep 23 - Fri, Sep 26
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
American Airlines Logo
8:05 am - 11:38 amORD-PWM
2h 33mnonstop
$199American Airlines
Find Deal
Thu, Aug 14 - Tue, Aug 19
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
$200American Airlines
Find Deal
Thu, Aug 7 - Mon, Aug 11
United Airlines Logo
6:14 am - 8:05 amPWM-ORD
2h 51mnonstop
United Airlines Logo
3:50 pm - 11:03 pmORD-PWM
6h 13m1 stop
$209United Airlines
Find Deal
Tue, Aug 26 - Tue, Aug 26
United Airlines Logo
6:10 am - 8:05 amPWM-ORD
2h 55mnonstop
United Airlines Logo
6:25 pm - 9:59 pmORD-PWM
2h 34mnonstop
$217United Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 20
Delta Logo
1:39 pm - 8:47 pmPWM-ORD
8h 08m1 stop
Delta Logo
3:30 pm - 12:03 amORD-PWM
7h 33m1 stop
$219Delta
Find Deal
Wed, Aug 20 - Sat, Aug 23
Delta Logo
4:50 pm - 10:20 pmPWM-ORD
6h 30m1 stop
Delta Logo
2:25 pm - 12:03 amORD-PWM
8h 38m2 stops
$224Delta
Find Deal
Wed, Aug 20 - Sat, Aug 23
Southwest Logo
8:25 am - 12:45 pmPWM-ORD
5h 20m1 stop
Southwest Logo
11:25 am - 11:20 pmORD-PWM
10h 55m2 stops
$254Southwest
Find Deal
Thu, Aug 21 - Thu, Sep 4
Southwest Logo
5:50 am - 12:45 pmPWM-ORD
7h 55m1 stop
Southwest Logo
11:25 am - 10:25 pmORD-PWM
10h 00m2 stops
$260Southwest
Find Deal
Mon, Aug 25 - Tue, Aug 26

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

Our best JetBlue deals on Portland, Maine to Chicago O'Hare Intl Airport flight tickets
JetBlue
Oct 2
PWM7:30 amPortland
5h 40m
1 stop
ORD12:10 pmChicago O'Hare Intl
Oct 5
ORD6:45 amChicago O'Hare Intl
5h 37m
1 stop
PWM1:22 pmPortland
$183
Find similar
JetBlue
Sep 23
PWM7:09 amPortland
6h 01m
1 stop
ORD12:10 pmChicago O'Hare Intl
Sep 26
ORD1:36 pmChicago O'Hare Intl
7h 26m
1 stop
PWM10:02 pmPortland
$193
Find similar
JetBlue
Aug 27
PWM6:05 amPortland
6h 13m
1 stop
ORD11:18 amChicago O'Hare Intl
Aug 30
ORD6:15 amChicago O'Hare Intl
6h 08m
1 stop
PWM1:23 pmPortland
$195
Find similar

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
Aug 14
PWM6:30 amPortland
3h 02m
ORD8:32 amChicago O'Hare Intl
Aug 19
ORD8:05 amChicago O'Hare Intl
2h 33m
PWM11:38 amPortland
$199
Find similar
American Airlines
Aug 7
PWM6:30 amPortland
3h 02m
ORD8:32 amChicago O'Hare Intl
Aug 11
ORD8:13 pmChicago O'Hare Intl
2h 46m
PWM11:59 pmPortland
$200
Find similar
American Airlines
Aug 30
PWM7:53 amPortland
8h 52m
1 stop
ORD3:45 pmChicago O'Hare Intl
Sep 1
ORD8:05 amChicago O'Hare Intl
2h 33m
PWM11:38 amPortland
$221
Find similar

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $305.

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 $452. 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 $637.

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 $128 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $504. 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 $377 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 $228 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?

You could potentially save up to 7% on your flight if you consider stops on a Portland, Maine to Chicago O'Hare Intl Airport flight.

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

As of July 2025, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 44% 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

$100

Fastest flight time

2h 51m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Portland, Maine in the past 72 hours is $100. The best round-trip flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $183.
The fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 51m
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 51m.

  • 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
FrontierPriceFrom $39Free CancellationRating
5.9
3,251 reviews
Search Frontier flights
DeltaPriceFrom $124Free CancellationRating
8.0
7,958 reviews
Search Delta flights
American AirlinesPriceFrom $208Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
8,864 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 8,864 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 $209 (round-trip), much lower than the average airfare cost of $382 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 $208 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $312. American Airlines operates 14 flights to Chicago O'Hare Intl Airport from Portland, Maine in an average week. Users have rated it 7.2/10 across 10,000 reviews.

Traveling to a place near Chicago?

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

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 7/22
Tue 7/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago