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Cheap flights from Chicago to Portland, Maine from $53

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 1/13. 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.
9:35 am - 8:14 pmORD-PWM
9h 39m1 stop
8:01 pm - 9:24 amPWM-ORD
14h 23m1 stop
$118Frontier
Find Deal
Sun, Dec 15 - Tue, Dec 17
6:07 pm - 7:01 pmORD-PWM
23h 54m1 stop
11:23 am - 10:50 pmPWM-ORD
12h 27m1 stop
$136Frontier
Find Deal
Mon, Dec 16 - Mon, Dec 23
6:31 am - 12:05 pmORD-PWM
4h 34m1 stop
5:24 am - 10:58 amPWM-ORD
6h 34m1 stop
$198American Airlines
Find Deal
Tue, Dec 10 - Thu, Dec 12
6:31 am - 12:05 pmORD-PWM
4h 34m1 stop
5:39 am - 12:12 pmPWM-ORD
7h 33m1 stop
$213American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
6:00 am - 10:44 amPWM-ORD
5h 44m1 stop
$219United Airlines
Find Deal
Fri, Jan 3 - Tue, Jan 21
4:58 pm - 12:08 amMDW-PWM
6h 10m1 stop
6:05 am - 11:58 amPWM-MDW
6h 53m1 stop
$228Delta
Find Deal
Sat, Dec 14 - Mon, Dec 16
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$229United Airlines
Find Deal
Fri, Jan 3 - Tue, Jan 21
12:35 pm - 12:08 amORD-PWM
10h 33m2 stops
5:00 am - 10:05 amPWM-ORD
6h 05m1 stop
$233Delta
Find Deal
Tue, Dec 10 - Thu, Dec 12
7:20 am - 12:35 pmMDW-PWM
4h 15m1 stop
3:35 pm - 9:25 pmPWM-MDW
6h 50m1 stop
$298Southwest
Find Deal
Mon, Jan 6 - Tue, Jan 7
7:20 am - 12:35 pmMDW-PWM
4h 15m1 stop
6:00 am - 9:25 pmPWM-MDW
16h 25m2 stops
$312Southwest
Find Deal
Tue, Dec 3 - Wed, Dec 4
11:33 am - 8:12 pmMDW-PWM
7h 39m1 stop
$53Frontier
Find Deal
Mon, Jan 13
11:33 am - 8:12 pmMDW-PWM
7h 39m1 stop
$54Frontier
Find Deal
Mon, Jan 20
8:05 am - 4:37 pmORD-PWM
7h 32m1 stop
$99American Airlines
Find Deal
Mon, Jan 6
2:55 pm - 10:46 pmORD-PWM
6h 51m1 stop
$109American Airlines
Find Deal
Wed, Dec 18
8:35 am - 4:44 pmORD-PWM
7h 09m1 stop
$114Delta
Find Deal
Wed, Feb 19
4:58 pm - 12:10 amMDW-PWM
6h 12m1 stop
$114Delta
Find Deal
Wed, Dec 18
6:08 pm - 11:59 pmORD-PWM
4h 51m1 stop
$131United Airlines
Find Deal
Tue, Dec 24
8:48 am - 2:59 pmORD-PWM
5h 11m1 stop
$133United Airlines
Find Deal
Thu, Dec 12
8:10 am - 3:00 pmMDW-PWM
5h 50m1 stop
$149Southwest
Find Deal
Thu, Jan 23
2:25 pm - 10:15 pmMDW-PWM
6h 50m2 stops
$154Southwest
Find Deal
Sun, Jan 19
3:35 pm - 11:47 pmORD-PWM
7h 12m1 stop
6:00 am - 12:16 pmPWM-ORD
7h 16m1 stop
$323Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
3:19 pm - 11:47 pmMDW-PWM
7h 28m1 stop
6:00 am - 11:58 amPWM-MDW
6h 58m1 stop
$323Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:45 pm - 11:47 pmORD-PWM
5h 02m1 stop
6:00 am - 2:48 pmPWM-ORD
9h 48m2 stops
$328Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:00 pm - 9:30 pmORD-PWM
2h 30mnonstop
9:40 am - 2:19 pmPWM-ORD
5h 39m1 stop
$349United Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
6:00 pm - 9:30 pmORD-PWM
2h 30mnonstop
4:30 pm - 6:42 pmPWM-ORD
3h 12mnonstop
$371United Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
6:30 am - 2:35 pmMDW-PWM
7h 05m1 stop
3:10 pm - 10:00 pmPWM-MDW
7h 50m1 stop
$418Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
5:45 am - 2:35 pmORD-PWM
7h 50m1 stop
5:30 am - 1:00 pmPWM-ORD
8h 30m2 stops
$423Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
11:51 am - 11:14 amORD-PWM
22h 23m3 stops
6:14 pm - 9:06 amPWM-ORD
15h 52m2 stops
Fri, Nov 22 - Mon, Nov 25
10:25 am - 11:14 amORD-PWM
23h 49m2 stops
6:14 pm - 9:06 amPWM-ORD
15h 52m2 stops
Fri, Nov 22 - Mon, Nov 25
7:17 pm - 10:53 pmMDW-PWM
26h 36m3 stops
4:58 pm - 1:35 pmPWM-MDW
21h 37m3 stops
$1,802WestJet
Find Deal
Sat, Nov 23 - Mon, Nov 25
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$229United Airlines
Find Deal
Fri, Jan 3 - Tue, Jan 21
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$245United Airlines
Find Deal
Mon, Jan 6 - Tue, Jan 21
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$280United Airlines
Find Deal
Wed, Jan 8 - Tue, Jan 21
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
4:15 pm - 6:27 pmPWM-ORD
3h 12mnonstop
$289United Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10
11:05 am - 2:37 pmORD-PWM
2h 32mnonstop
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
$298United Airlines
Find Deal
Thu, Dec 19 - Thu, Jan 2
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$299United Airlines
Find Deal
Sun, Jan 5 - Tue, Jan 21
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$303United Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 21
6:10 pm - 9:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$314United Airlines
Find Deal
Fri, Jan 3 - Fri, Jan 10
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
$315United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
7:30 am - 9:44 amPWM-ORD
3h 14mnonstop
$321United Airlines
Find Deal
Tue, Dec 17 - Mon, Dec 23

Delta flights from Chicago to Portland, Maine

Our best Delta deals on Chicago to Portland, Maine flight tickets
Delta
Dec 14
MDW4:58 pmChicago Midway
6h 10m
1 stop
PWM12:08 amPortland
Dec 16
PWM6:05 amPortland
6h 53m
1 stop
MDW11:58 amChicago Midway
Delta
Dec 10
ORD12:35 pmChicago O'Hare Intl
10h 33m
2 stops
PWM12:08 amPortland
Dec 12
PWM5:00 amPortland
6h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
Delta
Jan 6
MDW6:00 amChicago Midway
9h 43m
2 stops
PWM4:43 pmPortland
Jan 21
PWM6:00 amPortland
12h 47m
2 stops
MDW5:47 pmChicago Midway

Southwest flights from Chicago to Portland, Maine

Our best Southwest deals on Chicago to Portland, Maine flight tickets
Southwest
Jan 6
MDW7:20 amChicago Midway
4h 15m
1 stop
PWM12:35 pmPortland
Jan 7
PWM3:35 pmPortland
6h 50m
1 stop
MDW9:25 pmChicago Midway
Southwest
Dec 3
MDW7:20 amChicago Midway
4h 15m
1 stop
PWM12:35 pmPortland
Dec 4
PWM6:00 amPortland
16h 25m
2 stops
MDW9:25 pmChicago Midway
Southwest
Feb 14
MDW2:30 pmChicago Midway
8h 25m
2 stops
PWM11:55 pmPortland
Feb 18
PWM1:25 pmPortland
9h 45m
2 stops
MDW10:10 pmChicago Midway

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 from Chicago to Portland, Maine?

January. The cheapest time of year to fly to Portland, Maine from Chicago is January. Most expensive is December

What is the cheapest day to depart Chicago for Portland, Maine?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from Chicago to Portland, Maine?

In the afternoon. Chicago to Portland, Maine flights are approximately 35% more expensive in the morning than in the afternoon

What is the cheapest airline that flies to Portland, Maine from Chicago?

Frontier. Frontier, Delta, and American Airlines are the most popular carriers operating from Chicago to Portland, Maine

What is the cheapest Chicago to Portland, Maine flight route?

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

How far in advance should you book Chicago to Portland, Maine flights?

59 days before. The cheapest time to buy a flight from Chicago to Portland, Maine is approximately 59 days to departure

How many flights depart from Chicago to Portland, Maine on average per day?

The number of flights available between Chicago and Portland, Maine is 5 per day as of November 2024. The most frequent departure time is 6:00PM, with 60% of daily flights leaving in the evening.

How many flights depart from Chicago to Portland, Maine on average per week?

As of November 2024, there are 35 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

Can stopping save me money on Chicago to Portland, Maine flights?

You could potentially save up to 66% 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 November 2024, prices for Chicago to Portland, Maine flights are approximately 27% cheaper 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

$53

Fastest flight time

2h 22m

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 $53. The best round-trip flight deal from Chicago to Portland, Maine found on momondo in the last 72 hours is $118.
The fastest flight from Chicago to Portland, Maine takes 2h 22m
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 22m.

  • 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
3,542 reviews
Search Frontier flights
American AirlinesPriceFrom $184Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,766 reviews
Search Delta flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,168 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Portland, Maine

    Across 14 United Airlines flights from Chicago to Portland, Maine this week, the average price was $404, with the best United Airlines deals starting from $217 round-trip. 9,168 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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