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Cheap flights from Chicago to Portland, Maine from $54

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 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 to Portland

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago 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 to Portland.

Cheap last minute flights

Planning a quick getaway from Chicago 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 to Portland

Find recent round-trip train or bus tickets from Chicago to Portland.

All round-trip flight deals to Portland

The cheapest plane tickets to Portland found on KAYAK recently.
11:33 am - 8:12 pmMDW-PWM
7h 39m1 stop
7:06 pm - 10:28 amPWM-MDW
16h 22m1 stop
$128Frontier
Find Deal
Mon, Jan 20 - Sun, Jan 26
5:40 am - 6:48 pmMDW-PWM
12h 08m1 stop
7:06 pm - 10:21 amPWM-MDW
16h 15m1 stop
$136Frontier
Find Deal
Fri, Jan 10 - Sun, Jan 12
6:06 am - 11:47 amORD-PWM
4h 41m1 stop
12:31 pm - 7:23 pmPWM-ORD
7h 52m1 stop
$168American Airlines
Find Deal
Thu, Feb 27 - Tue, Mar 4
6:30 am - 12:24 pmORD-PWM
4h 54m1 stop
5:20 pm - 10:16 pmPWM-ORD
5h 56m1 stop
$223American Airlines
Find Deal
Wed, Mar 5 - Mon, Mar 10
7:05 am - 2:22 pmORD-PWM
6h 17m1 stop
5:25 pm - 10:36 pmPWM-ORD
6h 11m1 stop
$228Delta
Find Deal
Fri, Jan 31 - Fri, Feb 7
10:30 am - 4:06 pmORD-PWM
4h 36m1 stop
7:15 am - 12:55 pmPWM-ORD
6h 40m2 stops
$233Delta
Find Deal
Fri, Jan 31 - Sun, Feb 2
4:31 pm - 11:47 pmORD-PWM
6h 16m1 stop
6:00 am - 8:05 amPWM-ORD
3h 05mnonstop
$236United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
6:00 pm - 9:22 pmORD-PWM
2h 22mnonstop
6:00 am - 8:05 amPWM-ORD
3h 05mnonstop
$240United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
7:00 am - 3:45 pmORD-PWM
7h 45m2 stops
3:35 pm - 10:20 pmPWM-ORD
7h 45m1 stop
$303Southwest
Find Deal
Thu, Jan 16 - Tue, Jan 21
7:30 am - 10:40 pmORD-PWM
14h 10m2 stops
5:35 am - 4:45 pmPWM-ORD
12h 10m2 stops
$308Southwest
Find Deal
Fri, Feb 7 - Sun, Feb 9
7:25 am - 5:38 pmORD-PWM
9h 13m1 stop
$54Frontier
Find Deal
Wed, Feb 26
11:33 am - 8:12 pmMDW-PWM
7h 39m1 stop
$54Frontier
Find Deal
Mon, Jan 20
8:05 am - 1:54 pmORD-PWM
4h 49m1 stop
$84American Airlines
Find Deal
Thu, Feb 6
7:05 am - 2:22 pmORD-PWM
6h 17m1 stop
$114Delta
Find Deal
Thu, Jan 23
5:07 pm - 11:51 pmMDW-PWM
5h 44m1 stop
$114Delta
Find Deal
Wed, Jan 15
6:30 am - 2:52 pmORD-PWM
7h 22m1 stop
$132United Airlines
Find Deal
Sun, Mar 9
6:30 am - 2:52 pmORD-PWM
7h 22m1 stop
$133United Airlines
Find Deal
Thu, Mar 27
6:00 am - 11:21 amORD-PWM
4h 21m1 stop
$139American Airlines
Find Deal
Fri, Apr 25
6:35 am - 12:10 pmMDW-PWM
4h 35m1 stop
$149Southwest
Find Deal
Sat, Jan 18
7:00 am - 4:35 pmORD-PWM
8h 35m2 stops
$154Southwest
Find Deal
Thu, Feb 13
4:21 pm - 12:37 amORD-PWM
7h 16m1 stop
5:39 am - 11:01 amPWM-ORD
6h 22m1 stop
$358American Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
6:39 pm - 12:37 amORD-PWM
4h 58m1 stop
5:39 am - 11:01 amPWM-ORD
6h 22m1 stop
$372American Airlines
Find Deal
Mon, Dec 23 - Fri, Dec 27
6:30 am - 10:23 amORD-PWM
26h 53m1 stop
7:51 pm - 9:54 amPWM-ORD
15h 03m1 stop
$388Frontier
Find Deal
Thu, Dec 19 - Sun, Dec 22
2:55 pm - 12:05 amORD-PWM
8h 10m2 stops
5:30 am - 2:00 pmPWM-ORD
9h 30m1 stop
$423Southwest
Find Deal
Mon, Dec 23 - Mon, Dec 30
4:00 pm - 12:05 amORD-PWM
7h 05m1 stop
2:15 pm - 9:30 pmPWM-ORD
8h 15m1 stop
$453Southwest
Find Deal
Fri, Dec 20 - Mon, Dec 23
6:49 pm - 7:01 pmMDW-PWM
23h 12m1 stop
7:51 pm - 9:31 amPWM-MDW
14h 40m1 stop
$559Frontier
Find Deal
Mon, Dec 23 - Sun, Dec 29
6:25 pm - 11:22 pmMDW-PWM
3h 57m1 stop
5:05 am - 8:50 amPWM-MDW
4h 45m1 stop
$668Delta
Find Deal
Mon, Dec 23 - Mon, Dec 30
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
$748United Airlines
Find Deal
Thu, Dec 19 - Sun, Dec 22
6:25 pm - 11:22 pmMDW-PWM
3h 57m1 stop
6:05 am - 11:21 amPWM-MDW
6h 16m1 stop
$758Delta
Find Deal
Mon, Dec 23 - Fri, Dec 27
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
7:16 pm - 11:25 pmPWM-ORD
5h 09m1 stop
$759United Airlines
Find Deal
Mon, Dec 23 - Thu, Dec 26
6:00 pm - 9:22 pmORD-PWM
2h 22mnonstop
6:00 am - 8:05 amPWM-ORD
3h 05mnonstop
$240United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$259American Airlines
Find Deal
Wed, Jun 11 - Fri, Jun 20
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$279United Airlines
Find Deal
Thu, Jan 9 - Sat, Jan 11
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$289United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$338American Airlines
Find Deal
Sat, Jun 14 - Sun, Jun 22
6:20 pm - 9:44 pmORD-PWM
2h 24mnonstop
12:31 pm - 2:20 pmPWM-ORD
2h 49mnonstop
$373American Airlines
Find Deal
Sun, Jun 15 - Fri, Jun 27
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$374United Airlines
Find Deal
Fri, Jan 17 - Tue, Jan 21
9:20 am - 12:35 pmMDW-PWM
2h 15mnonstop
7:55 pm - 9:30 pmPWM-MDW
2h 35mnonstop
$412Southwest
Find Deal
Fri, Jun 13 - Sun, Jun 22
9:45 am - 1:00 pmMDW-PWM
2h 15mnonstop
7:40 pm - 9:15 pmPWM-MDW
2h 35mnonstop
$502Southwest
Find Deal
Wed, Jun 11 - Fri, Jun 20
9:15 am - 12:30 pmMDW-PWM
2h 15mnonstop
7:55 pm - 9:30 pmPWM-MDW
2h 35mnonstop
$547Southwest
Find Deal
Sat, Jun 14 - Sun, Jun 22

American Airlines flights from Chicago to Portland, Maine

Our best American Airlines deals on Chicago to Portland, Maine flight tickets
American Airlines
Feb 27
ORD6:06 amChicago O'Hare Intl
4h 41m
1 stop
PWM11:47 amPortland
Mar 4
PWM12:31 pmPortland
7h 52m
1 stop
ORD7:23 pmChicago O'Hare Intl
American Airlines
Mar 5
ORD6:30 amChicago O'Hare Intl
4h 54m
1 stop
PWM12:24 pmPortland
Mar 10
PWM5:20 pmPortland
5h 56m
1 stop
ORD10:16 pmChicago O'Hare Intl
American Airlines
Jun 11
ORD6:01 amChicago O'Hare Intl
4h 04m
1 stop
PWM11:05 amPortland
Jun 20
PWM7:17 amPortland
2h 53m
ORD9:10 amChicago O'Hare Intl

Delta flights from Chicago to Portland, Maine

Our best Delta deals on Chicago to Portland, Maine flight tickets
Delta
Jan 31
ORD7:05 amChicago O'Hare Intl
6h 17m
1 stop
PWM2:22 pmPortland
Feb 7
PWM5:25 pmPortland
6h 11m
1 stop
ORD10:36 pmChicago O'Hare Intl
Delta
Jan 31
MDW9:34 amChicago Midway
5h 32m
1 stop
PWM4:06 pmPortland
Feb 7
PWM6:00 amPortland
12h 43m
2 stops
MDW5:43 pmChicago Midway
Delta
Feb 16
ORD10:30 amChicago O'Hare Intl
12h 26m
2 stops
PWM11:56 pmPortland
Feb 22
PWM4:46 pmPortland
8h 02m
2 stops
ORD11:48 pmChicago O'Hare Intl

See travel insights to Portland from

How to get the cheapest flight ticket from Chicago 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 and Portland, Maine?

What is the cheapest month to fly to Portland, Maine?

The cheapest month to fly to Portland, Maine from Chicago is in June. Flight prices, which tend to average around $288, 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 June, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $304.

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 is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $218. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $411.

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 to Portland, Maine when you can find flight prices for as low as $247. 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 $379. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Portland flight route?

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

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

The ideal time to book your flight to Portland, Maine is 49 days in advance when prices tend to average $397. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $70.

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago 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 to Portland, Maine flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago to Portland, Maine flight.

How have Chicago to Portland, Maine flight prices changed over time?

As of December 2024, prices for Chicago to Portland, Maine flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Portland, Maine

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

Cheap Chicago to Portland, Maine (CHI to PWM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland, Maine

Best Price Found

$54

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Portland, Maine

1 airport
The best one-way flight to Portland, Maine from Chicago in the past 72 hours is $54. The best round-trip flight deal from Chicago to Portland, Maine found on momondo in the last 72 hours is $128.
The fastest flight from Chicago to Portland, Maine takes 2h 10m
Direct flights go from Chicago to Portland, Maine every day.
There is 1 airport near Portland, Maine: Portland (PWM)

  • How far is Chicago to Portland by plane?

    Chicago and Portland are 887.4 mi apart from one another. By plane, this route typically takes 2h 15m.

  • When did momondo last update prices for flights from Chicago to Portland Airport?

    Prices for flights from Chicago to Portland Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Portland Airport?

  • How old do you have to be to fly from Chicago 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 to Portland Airport.

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

    The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Portland, Maine?

  • What is the most popular airline from Chicago to Portland, Maine?


Best airlines flying from Chicago to Portland, Maine

Compare and see reviews for airlines that fly from Chicago to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $38Free CancellationRating
6.1
3,479 reviews
Search Frontier flights
American AirlinesPriceFrom $184Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,604 reviews
Search Delta flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Portland, Maine

    Across 6 United Airlines flights from Chicago to Portland, Maine this week, the average price was $408, with the best United Airlines deals starting from $217 round-trip. 9,059 users have rated United Airlines on momondo, with an average score of 7.4/10.


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?

Yes. All flights to Portland from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Chicago and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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