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Cheap flights from Chicago O'Hare Intl Airport to Portland, Maine from $55

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 2/26. 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

These are some of the best round-trip flight deals from Chicago O'Hare Intl Airport to Portland that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago O'Hare Intl Airport to Portland.

Cheap last minute flights

Planning a quick getaway from Chicago O'Hare Intl Airport to Portland? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Portland, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago O'Hare Intl Airport to Portland

Find recent round-trip train or bus tickets from Chicago O'Hare Intl Airport to Portland.

All round-trip flight deals from Chicago O'Hare Intl Airport to Portland

The cheapest plane tickets from Chicago O'Hare Intl Airport to Portland found on KAYAK recently.
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
10:08 am - 10:38 pmPWM-ORD
13h 30m1 stop
$130Frontier
Find Deal
mié., feb. 26 - mar., mar. 4
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
7:34 pm - 10:57 amPWM-ORD
16h 23m1 stop
$140Frontier
Find Deal
mié., mar. 5 - lun., mar. 10
6:20 am - 2:25 pmORD-PWM
7h 05m1 stop
7:15 am - 12:17 pmPWM-ORD
6h 02m1 stop
$185JetBlue
Find Deal
jue., may. 1 - lun., may. 12
1:12 pm - 9:57 pmORD-PWM
7h 45m1 stop
7:15 am - 12:17 pmPWM-ORD
6h 02m1 stop
$207JetBlue
Find Deal
jue., may. 1 - lun., may. 5
6:20 pm - 9:50 pmORD-PWM
2h 30mnonstop
7:19 am - 9:10 amPWM-ORD
2h 51mnonstop
$209American Airlines
Find Deal
sáb., jul. 5 - mié., jul. 9
7:05 am - 2:22 pmORD-PWM
6h 17m1 stop
12:01 pm - 6:41 pmPWM-ORD
7h 40m1 stop
$217Delta
Find Deal
mar., feb. 25 - mar., mar. 4
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$219United Airlines
Find Deal
mié., feb. 5 - mié., feb. 12
1:40 pm - 11:10 pmORD-PWM
8h 30m2 stops
12:01 pm - 6:41 pmPWM-ORD
7h 40m1 stop
$222Delta
Find Deal
mié., feb. 26 - mar., mar. 4
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
6:00 am - 11:38 amPWM-ORD
6h 38m1 stop
$229United Airlines
Find Deal
mié., feb. 5 - mié., feb. 12
6:16 am - 11:38 amORD-PWM
4h 22m1 stop
12:05 pm - 1:59 pmPWM-ORD
2h 54mnonstop
$262American Airlines
Find Deal
mar., abr. 29 - sáb., may. 10
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
$55Frontier
Find Deal
mié., feb. 26
5:10 am - 7:35 pmORD-PWM
13h 25m1 stop
$61Frontier
Find Deal
lun., mar. 3
6:20 am - 1:20 pmORD-PWM
6h 00m1 stop
$82JetBlue
Find Deal
sáb., may. 10
1:22 pm - 11:00 pmORD-PWM
8h 38m1 stop
$87JetBlue
Find Deal
lun., abr. 7
7:05 am - 2:22 pmORD-PWM
6h 17m1 stop
$109Delta
Find Deal
mar., feb. 25
1:40 pm - 11:10 pmORD-PWM
8h 30m2 stops
$114Delta
Find Deal
mié., feb. 26
6:45 am - 12:10 pmORD-PWM
4h 25m1 stop
$129American Airlines
Find Deal
vie., abr. 18
3:00 pm - 11:15 pmORD-PWM
7h 15m1 stop
$137United Airlines
Find Deal
jue., mar. 13
6:06 am - 11:47 amORD-PWM
4h 41m1 stop
$140American Airlines
Find Deal
dom., mar. 2
3:00 pm - 11:27 pmORD-PWM
7h 27m1 stop
$182United Airlines
Find Deal
lun., abr. 28
4:55 pm - 11:51 pmORD-PWM
5h 56m1 stop
4:46 pm - 9:15 pmPWM-ORD
5h 29m1 stop
$369Delta
Find Deal
vie., ene. 24 - dom., feb. 2
11:05 am - 11:10 pmORD-PWM
11h 05m2 stops
5:34 am - 1:49 pmPWM-ORD
9h 15m1 stop
$374Delta
Find Deal
vie., ene. 24 - dom., feb. 2
1:40 pm - 11:10 pmORD-PWM
8h 30m2 stops
5:23 am - 3:45 pmPWM-ORD
11h 22m2 stops
$379Delta
Find Deal
dom., ene. 26 - vie., ene. 31
11:25 am - 10:15 pmORD-PWM
9h 50m2 stops
6:00 am - 6:10 pmPWM-ORD
13h 10m2 stops
$409Southwest
Find Deal
vie., ene. 24 - dom., feb. 2
2:20 pm - 10:30 pmORD-PWM
7h 10m1 stop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$419United Airlines
Find Deal
sáb., ene. 25 - lun., ene. 27
12:40 pm - 10:05 pmORD-PWM
8h 25m1 stop
3:35 pm - 10:20 pmPWM-ORD
7h 45m1 stop
$429Southwest
Find Deal
sáb., ene. 25 - lun., ene. 27
1:30 pm - 10:05 pmORD-PWM
7h 35m2 stops
5:35 am - 2:00 pmPWM-ORD
9h 25m1 stop
$434Southwest
Find Deal
sáb., ene. 25 - lun., ene. 27
5:35 am - 5:10 pmORD-PWM
34h 35m3 stops
6:18 pm - 12:57 pmPWM-ORD
19h 39m2 stops
dom., ene. 26 - vie., ene. 31
5:35 am - 5:10 pmORD-PWM
34h 35m3 stops
6:18 pm - 8:13 pmPWM-ORD
26h 55m3 stops
dom., ene. 26 - vie., ene. 31
3:15 pm - 10:30 pmORD-PWM
6h 15m1 stop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$529United Airlines
Find Deal
vie., ene. 24 - dom., feb. 2
6:20 pm - 9:50 pmORD-PWM
2h 30mnonstop
7:19 am - 9:10 amPWM-ORD
2h 51mnonstop
$209American Airlines
Find Deal
sáb., jul. 5 - mié., jul. 9
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$219United Airlines
Find Deal
mié., feb. 5 - mié., feb. 12
8:00 am - 11:34 amORD-PWM
2h 34mnonstop
7:19 am - 9:10 amPWM-ORD
2h 51mnonstop
$258American Airlines
Find Deal
mié., jul. 2 - mié., jul. 9
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$259United Airlines
Find Deal
mar., feb. 4 - sáb., feb. 8
11:10 am - 2:32 pmORD-PWM
2h 22mnonstop
4:04 pm - 6:10 pmPWM-ORD
3h 06mnonstop
$279United Airlines
Find Deal
mar., feb. 25 - mié., mar. 5
8:09 am - 11:41 amORD-PWM
2h 32mnonstop
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$283American Airlines
Find Deal
mié., jun. 4 - jue., jun. 5
6:00 pm - 9:27 pmORD-PWM
2h 27mnonstop
6:00 am - 7:57 amPWM-ORD
2h 57mnonstop
$289United Airlines
Find Deal
mié., jun. 18 - sáb., jun. 21
11:10 am - 2:32 pmORD-PWM
2h 22mnonstop
4:04 pm - 6:10 pmPWM-ORD
3h 06mnonstop
$314United Airlines
Find Deal
mié., feb. 26 - mié., mar. 5
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$327American Airlines
Find Deal
sáb., jun. 21 - sáb., jun. 28
11:59 am - 3:21 pmORD-PWM
2h 22mnonstop
4:04 pm - 6:10 pmPWM-ORD
3h 06mnonstop
$331United Airlines
Find Deal
jue., feb. 13 - mié., feb. 19

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
Feb 26
ORD7:25 amChicago O'Hare Intl
9h 13m
1 stop
PWM5:38 pmPortland
Mar 4
PWM10:08 amPortland
13h 30m
1 stop
ORD10:38 pmChicago O'Hare Intl
Frontier
Mar 5
ORD7:25 amChicago O'Hare Intl
9h 13m
1 stop
PWM5:38 pmPortland
Mar 10
PWM7:34 pmPortland
16h 23m
1 stop
ORD10:57 amChicago O'Hare Intl
Frontier
Mar 1
ORD8:44 pmChicago O'Hare Intl
11h 34m
1 stop
PWM9:18 amPortland
Mar 4
PWM10:08 amPortland
13h 30m
1 stop
ORD10:38 pmChicago O'Hare Intl

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 1
ORD6:20 amChicago O'Hare Intl
7h 05m
1 stop
PWM2:25 pmPortland
May 12
PWM7:15 amPortland
6h 02m
1 stop
ORD12:17 pmChicago O'Hare Intl
JetBlue
May 1
ORD1:12 pmChicago O'Hare Intl
7h 45m
1 stop
PWM9:57 pmPortland
May 5
PWM7:15 amPortland
6h 02m
1 stop
ORD12:17 pmChicago O'Hare Intl
JetBlue
Apr 29
ORD1:22 pmChicago O'Hare Intl
8h 38m
1 stop
PWM11:00 pmPortland
May 7
PWM3:20 pmPortland
8h 00m
1 stop
ORD10:20 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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Portland, Maine?

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 June is also cheap. Prices for this month can be found on momondo for an average of $294.

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 $200. 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 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 $214. 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 $393. 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 $403 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 $203 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 January 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 9% more expensive 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

$55

Fastest flight time

2h 18m

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 $55. The best round-trip flight deal from Chicago O'Hare Intl Airport to Portland, Maine found on momondo in the last 72 hours is $130.
The fastest flight from Chicago O'Hare Intl Airport to Portland, Maine takes 2h 18m
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 22m.

  • 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
6.0
3,440 reviews
Search Frontier flights
American AirlinesPriceFrom $181Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $217Free CancellationRating
8.0
8,508 reviews
Search Delta flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
8,970 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 $222 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $408 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
Freeport
Gorham
Bartlett
Lewiston
Conway
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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