Cheap flights from Chicago O'Hare Intl Airport to Portland 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 Chicago O'Hare Intl Airport to Portland 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 Chicago O'Hare Intl Airport to Portland

Cheap round-trip flights

JetBlue Logo
6:10 am - 1:22 pmORD-PWM
6h 12m1 stop
JetBlue Logo
7:30 am - 12:10 pmPWM-ORD
5h 40m1 stop
$183JetBlue
Find Deal
Wed, Sep 3 - Tue, Sep 9
JetBlue Logo
1:35 pm - 10:07 pmORD-PWM
7h 32m1 stop
JetBlue Logo
7:09 am - 12:21 pmPWM-ORD
6h 12m1 stop
$185JetBlue
Find Deal
Fri, Sep 26 - Mon, Sep 29
JetBlue Logo
6:15 am - 1:23 pmORD-PWM
6h 08m1 stop
JetBlue Logo
6:05 am - 12:40 pmPWM-ORD
7h 35m1 stop
$190JetBlue
Find Deal
Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
8:15 am - 11:49 amORD-PWM
2h 34mnonstop
American Airlines Logo
6:01 am - 7:57 amPWM-ORD
2h 56mnonstop
$199American Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
10:58 am - 2:26 pmORD-PWM
2h 28mnonstop
United Airlines Logo
5:02 pm - 6:53 pmPWM-ORD
2h 51mnonstop
$208United Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
United Airlines Logo
6:10 pm - 9:44 pmORD-PWM
2h 34mnonstop
United Airlines Logo
6:00 am - 11:46 amPWM-ORD
6h 46m1 stop
$209United Airlines
Find Deal
Wed, Oct 22 - Tue, Oct 28
American Airlines Logo
7:10 pm - 10:43 pmORD-PWM
2h 33mnonstop
American Airlines Logo
6:01 am - 7:57 amPWM-ORD
2h 56mnonstop
$217American Airlines
Find Deal
Wed, Sep 3 - Tue, Sep 9
Delta Logo
6:00 am - 12:59 pmORD-PWM
5h 59m1 stop
Delta Logo
5:30 pm - 11:56 pmPWM-ORD
7h 26m1 stop
$219Delta
Find Deal
Tue, Aug 26 - Sat, Aug 30
Delta Logo
7:15 am - 12:59 pmORD-PWM
4h 44m1 stop
Delta Logo
5:30 pm - 11:56 pmPWM-ORD
7h 26m1 stop
$228Delta
Find Deal
Tue, Aug 26 - Sat, Aug 30
Frontier Logo
4:26 pm - 6:13 pmORD-PWM
24h 47m1 stop
Frontier Logo
1:41 pm - 6:41 pmPWM-ORD
30h 00m1 stop
$275Frontier
Find Deal
Fri, Aug 8 - Sat, Aug 23

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

Our best Frontier deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets
Frontier
Aug 9
ORD9:08 amChicago O'Hare Intl
8h 05m
1 stop
PWM6:13 pmPortland
Aug 16
PWM6:58 pmPortland
21h 55m
1 stop
ORD3:53 pmChicago O'Hare Intl
Frontier
Aug 2
ORD9:08 amChicago O'Hare Intl
8h 05m
1 stop
PWM6:13 pmPortland
Aug 16
PWM6:58 pmPortland
21h 55m
1 stop
ORD3:53 pmChicago O'Hare Intl
Frontier
Aug 8
ORD4:26 pmChicago O'Hare Intl
24h 47m
1 stop
PWM6:13 pmPortland
Aug 23
PWM1:41 pmPortland
30h 00m
1 stop
ORD6:41 pmChicago O'Hare Intl

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets
American Airlines
Sep 16
ORD8:15 amChicago O'Hare Intl
2h 34m
PWM11:49 amPortland
Sep 23
PWM6:01 amPortland
2h 56m
ORD7:57 amChicago O'Hare Intl
American Airlines
Sep 3
ORD7:10 pmChicago O'Hare Intl
2h 33m
PWM10:43 pmPortland
Sep 9
PWM6:01 amPortland
2h 56m
ORD7:57 amChicago O'Hare Intl
American Airlines
Aug 23
ORD1:20 pmChicago O'Hare Intl
7h 25m
1 stop
PWM9:45 pmPortland
Aug 30
PWM6:30 amPortland
3h 02m
ORD8:32 amChicago O'Hare Intl

See travel insights to Portland from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Portland, Maine

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 Portland, Maine?

The cheapest month to fly to Portland, Maine from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $315, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $319.

What is the cheapest day to depart on your flight to Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Chicago O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $324. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $401.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Portland, Maine when you can find flight prices for as low as $304. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago O'Hare Intl to Portland flight route?

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

How far in advance should I book a flight to Portland, Maine?

You are more likely to see cheaper flights to Portland, Maine from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $394 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Chicago O'Hare Intl Airport for as low as $282 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Portland 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 Chicago O'Hare Intl Airport to Portland, Maine flights?

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

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

As of July 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 30% cheaper when compared to flights at the same time last year.

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

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

Cheap Chicago O'Hare Intl Airport to Portland, Maine (ORD to PWM) flight deals and tips

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

Best Price Found

$100

Fastest flight time

2h 17m

Direct flights

Every day

Airports in Portland, Maine

1 airport
The best one-way flight to Portland, Maine from Chicago O'Hare Intl Airport in the past 72 hours is $100. The best round-trip flight deal from Chicago O'Hare Intl Airport to Portland, Maine found on momondo in the last 72 hours is $183.
The fastest flight from Chicago O'Hare Intl Airport to Portland, Maine takes 2h 17m
Direct flights go from Chicago O'Hare Intl Airport to Portland, Maine every day.
There is 1 airport near Portland, Maine: Portland (PWM)

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

    Chicago O'Hare Intl and Portland are 899.6 mi apart from one another. By plane, this route typically takes 2h 28m.

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

    Prices for flights from Chicago O'Hare Intl Airport to Portland Airport are updated daily.

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

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

  • What documentation or ID do you need to fly to Portland Airport?

    The travel and health documents you'll need for your trip to Portland Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Portland Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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


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

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $68Free CancellationRating
5.9
3,238 reviews
Search Frontier flights
DeltaPriceFrom $163Free CancellationRating
8.0
7,971 reviews
Search Delta flights
American AirlinesPriceFrom $203Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $213Free CancellationRating
7.4
8,893 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago O'Hare Intl Airport to Portland, Maine

    United Airlines flight deals from Chicago O'Hare Intl Airport to Portland, Maine start from $213 round-trip. Over the 19 United Airlines flights for this route in a normal week, average airfare is usually $388 round-trip - but some users have found much cheaper deals with momondo.

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

    The best American Airlines deal for Chicago O'Hare Intl Airport to Portland, Maine flight tickets found on momondo in the last 72 hours was $203, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $343 round-trip. American Airlines operates 15 flights out of Chicago O'Hare Intl Airport into Portland, Maine in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.


Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Bartlett
Lewiston
Brunswick
Gorham
Auburn
Intervale
Windham
Bath
Falmouth
Oxford
Tamworth
Georgetown

Why use momondo?

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

It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

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

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

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

Once you have performed a search for Chicago to Portland 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 Chicago to Portland right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Portland, momondo offers a useful price alert feature which will track prices for flights to Portland from Chicago and alert you when they change.


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1 adult
Sat 8/2
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