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Cheap flights from Chicago O'Hare Intl Airport to Portland, Maine from $90

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, Maine departing on 8/31. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago O'Hare Intl Airport to Portland.
JetBlue Logo
4:03 pm - 10:59 pmORD-PWM
5h 56m1 stop
JetBlue Logo
3:35 pm - 9:54 pmPWM-ORD
7h 19m1 stop
$163JetBlue
Find Deal
Fri, May 9 - Tue, May 20
JetBlue Logo
4:03 pm - 10:59 pmORD-PWM
5h 56m1 stop
JetBlue Logo
7:12 am - 3:04 pmPWM-ORD
8h 52m1 stop
$183JetBlue
Find Deal
Fri, May 9 - Sun, May 11
Frontier Logo
4:15 pm - 6:26 pmORD-PWM
25h 11m1 stop
Frontier Logo
8:23 pm - 11:32 pmPWM-ORD
28h 09m1 stop
$200Frontier
Find Deal
Fri, May 9 - Sun, May 18
Frontier Logo
4:15 pm - 8:40 pmORD-PWM
27h 25m1 stop
Frontier Logo
8:23 pm - 11:32 pmPWM-ORD
28h 09m1 stop
$208Frontier
Find Deal
Thu, May 8 - Sun, May 11
American Airlines Logo
7:10 pm - 10:43 pmORD-PWM
2h 33mnonstop
American Airlines Logo
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
$209American Airlines
Find Deal
Thu, Jun 26 - Sun, Jun 29
Delta Logo
3:40 pm - 12:28 amORD-PWM
7h 48m1 stop
Delta Logo
6:56 pm - 11:59 pmPWM-ORD
6h 03m1 stop
$217Delta
Find Deal
Tue, Jul 1 - Wed, Jul 2
American Airlines Logo
8:00 am - 11:32 amORD-PWM
2h 32mnonstop
American Airlines Logo
6:01 pm - 11:57 pmPWM-ORD
6h 56m1 stop
$219American Airlines
Find Deal
Tue, Jul 8 - Tue, Jul 15
United Airlines Logo
5:53 pm - 9:16 pmORD-PWM
2h 23mnonstop
United Airlines Logo
6:00 am - 7:53 amPWM-ORD
2h 53mnonstop
$224United Airlines
Find Deal
Tue, May 20 - Thu, May 29
Delta Logo
3:40 pm - 12:28 amORD-PWM
7h 48m1 stop
Delta Logo
6:56 pm - 11:59 pmPWM-ORD
6h 03m1 stop
$233Delta
Find Deal
Tue, Jul 1 - Thu, Jul 3
United Airlines Logo
4:46 pm - 11:14 pmORD-PWM
5h 28m1 stop
United Airlines Logo
6:10 am - 8:05 amPWM-ORD
2h 55mnonstop
$240United Airlines
Find Deal
Fri, Jul 11 - Thu, Jul 24

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
May 9
ORD4:15 pmChicago O'Hare Intl
25h 11m
1 stop
PWM6:26 pmPortland
May 18
PWM8:23 pmPortland
28h 09m
1 stop
ORD11:32 pmChicago O'Hare Intl
Frontier
May 8
ORD4:15 pmChicago O'Hare Intl
27h 25m
1 stop
PWM8:40 pmPortland
May 11
PWM8:23 pmPortland
28h 09m
1 stop
ORD11:32 pmChicago O'Hare Intl
Frontier
Apr 19
ORD9:25 amChicago O'Hare Intl
22h 47m
1 stop
PWM9:12 amPortland
Apr 24
PWM8:01 pmPortland
28h 35m
1 stop
ORD11:36 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
Jun 26
ORD7:10 pmChicago O'Hare Intl
2h 33m
PWM10:43 pmPortland
Jun 29
PWM6:00 amPortland
2h 57m
ORD7:57 amChicago O'Hare Intl
American Airlines
Jul 8
ORD8:00 amChicago O'Hare Intl
2h 32m
PWM11:32 amPortland
Jul 15
PWM6:01 pmPortland
6h 56m
1 stop
ORD11:57 pmChicago O'Hare Intl
American Airlines
Jun 21
ORD7:01 amChicago O'Hare Intl
7h 19m
1 stop
PWM3:20 pmPortland
Jun 28
PWM7:41 amPortland
5h 38m
1 stop
ORD12:19 pmChicago 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 July. Flight prices, which tend to average around $283, 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 July, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $305.

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 $193. 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 $395.

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

In the afternoon 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 $210. Flying to Portland, Maine in the afternoon 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 $382. 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 7 weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $390 when searching 7 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 $239 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.

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

As of April 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 49% 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

$90

Fastest flight time

2h 15m

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 $90. The best round-trip flight deal from Chicago O'Hare Intl Airport to Portland, Maine found on momondo in the last 72 hours is $163.
The fastest flight from Chicago O'Hare Intl Airport to Portland, Maine takes 2h 15m
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 15m.

  • 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 $38Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $217Free CancellationRating
8.0
7,899 reviews
Search Delta flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,615 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 $218 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $389 round-trip - but some users have found much cheaper deals with momondo.


Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Jackson
Boothbay Harbor
Conway
Freeport
Bartlett
Lewiston
Gorham
Brunswick
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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