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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 5/28. 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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0 bags

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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 - 11:00 pmORD-PWM
5h 57m1 stop
JetBlue Logo
3:35 pm - 9:54 pmPWM-ORD
7h 19m1 stop
$183JetBlue
Find Deal
Wed, May 14 - Wed, May 21
United Airlines Logo
9:00 am - 5:43 pmORD-PWM
7h 43m1 stop
United Airlines Logo
4:43 pm - 6:40 pmPWM-ORD
2h 57mnonstop
$189United Airlines
Find Deal
Wed, May 28 - Sat, May 31
Frontier Logo
4:15 pm - 6:26 pmORD-PWM
25h 11m1 stop
Frontier Logo
8:23 pm - 11:32 pmPWM-ORD
28h 09m1 stop
$201Frontier
Find Deal
Fri, May 9 - Sun, May 11
Frontier Logo
4:15 pm - 7:33 pmORD-PWM
26h 18m1 stop
Frontier Logo
8:23 pm - 11:32 pmPWM-ORD
28h 09m1 stop
$211Frontier
Find Deal
Sat, May 10 - Sun, May 18
Delta Logo
3:59 pm - 12:14 amORD-PWM
7h 15m1 stop
Delta Logo
6:05 am - 12:41 pmPWM-ORD
7h 36m2 stops
$228Delta
Find Deal
Sat, May 31 - Sat, Jun 7
Delta Logo
5:35 am - 11:50 amORD-PWM
5h 15m1 stop
Delta Logo
1:53 pm - 8:42 pmPWM-ORD
7h 49m1 stop
$229Delta
Find Deal
Tue, Jun 24 - Wed, Jun 25
American Airlines Logo
7:12 pm - 10:46 pmORD-PWM
2h 34mnonstop
American Airlines Logo
5:57 am - 10:22 amPWM-ORD
5h 25m1 stop
$244American Airlines
Find Deal
Sat, Aug 23 - Sun, Sep 21
American Airlines Logo
8:00 am - 11:29 amORD-PWM
2h 29mnonstop
American Airlines Logo
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
$258American Airlines
Find Deal
Wed, Jun 11 - Sun, Jun 15
 Logo
5:08 pm - 6:02 pmORD-PWM
23h 54m1 stop
 Logo
12:40 pm - 5:27 pmPWM-ORD
5h 47m1 stop
Fri, Jun 6 - Sun, Jun 8
 Logo
7:47 am - 1:48 pmORD-PWM
29h 01m2 stops
 Logo
3:15 pm - 7:01 pmPWM-ORD
4h 46m1 stop
Wed, May 28 - Sun, Jun 1

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

Our best JetBlue deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets
JetBlue
May 14
ORD4:03 pmChicago O'Hare Intl
5h 57m
1 stop
PWM11:00 pmPortland
May 21
PWM3:35 pmPortland
7h 19m
1 stop
ORD9:54 pmChicago O'Hare Intl
JetBlue
May 31
ORD4:03 pmChicago O'Hare Intl
5h 56m
1 stop
PWM10:59 pmPortland
Jun 7
PWM2:15 pmPortland
8h 39m
1 stop
ORD9:54 pmChicago O'Hare Intl
JetBlue
Jul 9
ORD6:00 amChicago O'Hare Intl
6h 23m
1 stop
PWM1:23 pmPortland
Jul 12
PWM6:10 amPortland
5h 10m
1 stop
ORD10:20 amChicago O'Hare Intl

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

Our best Delta deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets
Delta
May 31
ORD3:59 pmChicago O'Hare Intl
7h 15m
1 stop
PWM12:14 amPortland
Jun 7
PWM6:05 amPortland
7h 36m
2 stops
ORD12:41 pmChicago O'Hare Intl
Delta
Jun 24
ORD5:35 amChicago O'Hare Intl
5h 15m
1 stop
PWM11:50 amPortland
Jun 25
PWM1:53 pmPortland
7h 49m
1 stop
ORD8:42 pmChicago O'Hare Intl
Delta
Jul 15
ORD1:16 pmChicago O'Hare Intl
9h 01m
2 stops
PWM11:17 pmPortland
Jul 22
PWM5:59 pmPortland
5h 47m
1 stop
ORD10:46 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 $300, 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 August is also cheap. Prices for this month can be found on momondo for an average of $302.

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 13 weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $379 when searching 13 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 $243 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 23m

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 $183.
The fastest flight from Chicago O'Hare Intl Airport to Portland, Maine takes 2h 23m
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 23m.

  • 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
3,283 reviews
Search Frontier flights
American AirlinesPriceFrom $177Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $211Free CancellationRating
7.4
8,684 reviews
Search United Airlines flights
DeltaPriceFrom $228Free CancellationRating
8.0
7,920 reviews
Search Delta 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 $211 round-trip. Over the 8 United Airlines flights for this route in a normal week, average airfare is usually $386 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
Bartlett
Lewiston
Gorham
Freeport
Brunswick
Auburn
Intervale
Bath
Windham
Falmouth
Tamworth
Georgetown
Oxford

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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