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Cheap flights from Chicago O'Hare Intl Airport to Portland from $67

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 11/18. 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
1:35 pm - 11:04 pmORD-PWM
8h 29m1 stop
JetBlue Logo
7:09 am - 12:22 pmPWM-ORD
6h 13m1 stop
$244JetBlue
Find Deal
Fri, Oct 17 - Tue, Oct 21
United Airlines Logo
2:20 pm - 11:13 pmORD-PWM
7h 53m1 stop
United Airlines Logo
6:25 pm - 8:25 pmPWM-ORD
3h 00mnonstop
$245United Airlines
Find Deal
Wed, Oct 1 - Fri, Oct 3
United Airlines Logo
6:10 pm - 9:44 pmORD-PWM
2h 34mnonstop
United Airlines Logo
5:41 pm - 11:30 pmPWM-ORD
6h 49m1 stop
$246United Airlines
Find Deal
Fri, Sep 26 - Tue, Sep 30
Southwest Logo
11:55 am - 10:15 pmORD-PWM
9h 20m2 stops
Southwest Logo
12:45 pm - 9:50 pmPWM-ORD
10h 05m2 stops
$247Southwest
Find Deal
Tue, Dec 16 - Tue, Jan 13
Delta Logo
7:10 am - 12:00 pmORD-PWM
3h 50m1 stop
Delta Logo
4:53 pm - 8:29 pmPWM-ORD
4h 36m1 stop
$248Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
6:45 am - 5:38 pmORD-PWM
9h 53m1 stop
American Airlines Logo
6:00 am - 11:06 amPWM-ORD
6h 06m1 stop
$250American Airlines
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
2:45 pm - 9:59 pmORD-PWM
6h 14m1 stop
Delta Logo
1:15 pm - 7:25 pmPWM-ORD
7h 10m1 stop
$251Delta
Find Deal
Tue, Jan 6 - Sat, Jan 10
Delta Logo
6:28 pm - 12:34 amORD-PWM
5h 06m1 stop
Delta Logo
6:00 am - 4:11 pmPWM-ORD
11h 11m2 stops
$253Delta
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
7:10 pm - 10:45 pmORD-PWM
2h 35mnonstop
American Airlines Logo
3:28 pm - 5:24 pmPWM-ORD
2h 56mnonstop
$262American Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
Southwest Logo
11:55 am - 10:15 pmORD-PWM
9h 20m2 stops
Southwest Logo
5:30 am - 2:45 pmPWM-ORD
10h 15m2 stops
$293Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8

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
Oct 18
ORD6:45 amChicago O'Hare Intl
9h 53m
1 stop
PWM5:38 pmPortland
Oct 21
PWM6:00 amPortland
6h 06m
1 stop
ORD11:06 amChicago O'Hare Intl
$250
Find similar
American Airlines
Oct 24
ORD7:10 pmChicago O'Hare Intl
2h 35m
PWM10:45 pmPortland
Oct 28
PWM3:28 pmPortland
2h 56m
ORD5:24 pmChicago O'Hare Intl
$262
Find similar
American Airlines
Sep 28
ORD8:15 amChicago O'Hare Intl
2h 34m
PWM11:49 amPortland
Oct 1
PWM1:02 pmPortland
8h 33m
1 stop
ORD8:35 pmChicago O'Hare Intl
$264
Find similar

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
Nov 6
ORD7:10 amChicago O'Hare Intl
3h 50m
1 stop
PWM12:00 pmPortland
Nov 9
PWM4:53 pmPortland
4h 36m
1 stop
ORD8:29 pmChicago O'Hare Intl
$248
Find similar
Delta
Jan 6
ORD2:45 pmChicago O'Hare Intl
6h 14m
1 stop
PWM9:59 pmPortland
Jan 10
PWM1:15 pmPortland
7h 10m
1 stop
ORD7:25 pmChicago O'Hare Intl
$251
Find similar
Delta
Oct 1
ORD6:28 pmChicago O'Hare Intl
5h 06m
1 stop
PWM12:34 amPortland
Oct 8
PWM6:00 amPortland
11h 11m
2 stops
ORD4:11 pmChicago O'Hare Intl
$253
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Portland, Maine that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 10/17

1:35 pm-11:04 pm

1 stop8h 29m

Portland

Tue 10/21

7:09 am-12:22 pm

1 stop6h 13m

$244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

2:20 pm-11:13 pm

1 stop7h 53m

Portland

Fri 10/3

6:25 pm-8:25 pm

Nonstop3h 00m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/26

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Tue 9/30

5:41 pm-11:30 pm

1 stop6h 49m

$246

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 12/16

11:55 am-10:15 pm

2 stops9h 20m

Portland

Tue 1/13

12:45 pm-9:50 pm

2 stops10h 05m

$247

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 11/6

7:10 am-12:00 pm

1 stop3h 50m

Portland

Sun 11/9

4:53 pm-8:29 pm

1 stop4h 36m

$248

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/18

6:45 am-5:38 pm

1 stop9h 53m

Portland

Tue 10/21

6:00 am-11:06 am

1 stop6h 06m

$250

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 1/6

2:45 pm-9:59 pm

1 stop6h 14m

Portland

Sat 1/10

1:15 pm-7:25 pm

1 stop7h 10m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

6:28 pm-12:34 am

1 stop5h 06m

Portland

Wed 10/8

6:00 am-4:11 pm

2 stops11h 11m

$253

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 10/24

7:10 pm-10:45 pm

Nonstop2h 35m

Portland

Tue 10/28

3:28 pm-5:24 pm

Nonstop2h 56m

$262

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 12/5

11:55 am-10:15 pm

2 stops9h 20m

Portland

Mon 12/8

5:30 am-2:45 pm

2 stops10h 15m

$293

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 August. Flight prices, which tend to average around $341, 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 August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $344.

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 $345. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday 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 $320. 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 afternoon because they tend to be around $378. 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 $401 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 September 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 8% 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

$194

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 $194. The best round-trip flight deal from Chicago O'Hare Intl Airport to Portland, Maine found on momondo in the last 72 hours is $272.
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)
Search flight deals

  • 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 19m.

  • 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
DeltaPriceFrom $163Free CancellationRating
7.9
7,960 reviews
Search Delta flights
United AirlinesPriceFrom $228Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
American AirlinesPriceFrom $231Free CancellationRating
7.2
10,000 reviews
Search American 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 $228 round-trip. Over the 21 United Airlines flights for this route in a normal week, average airfare is usually $387 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 $231, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $351 round-trip. American Airlines operates 17 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
Lewiston
Bartlett
Brunswick
Gorham
Auburn
Intervale
Windham
Bath
Oxford
Georgetown
Tamworth
Falmouth

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.

An easier way to manage your Portland, Maine 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.
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