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CHI - PWM

Find cheap flights from Chicago to Portland from $49

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portland departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

Search hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Chicago to Portland (CHI-PWM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:42 pm - 9:02 pmORD-PWM
2h 20mnonstop
9:55 pm - 11:38 pmPWM-ORD
2h 43mnonstop
$78Frontier
Find Deal
Tue, Jun 11 - Tue, Jun 18
6:02 pm - 9:22 pmORD-PWM
2h 20mnonstop
9:55 pm - 11:38 pmPWM-ORD
2h 43mnonstop
$82Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
1:14 pm - 8:10 pmPWM-ORD
7h 56m1 stop
Thu, Jun 13 - Sun, Jun 16
8:05 pm - 12:41 pmORD-PWM
15h 36m1 stop
9:55 pm - 11:38 pmPWM-ORD
2h 43mnonstop
Wed, Jun 19 - Tue, Jun 25
1:25 pm - 11:00 pmORD-PWM
8h 35m2 stops
11:30 am - 6:44 pmPWM-ORD
8h 14m2 stops
$218Delta
Find Deal
Tue, Jun 11 - Tue, Jun 18
1:24 pm - 11:00 pmMDW-PWM
8h 36m2 stops
11:30 am - 5:59 pmPWM-MDW
7h 29m2 stops
$218Delta
Find Deal
Tue, Jun 11 - Tue, Jun 18
7:15 pm - 10:43 pmORD-PWM
2h 28mnonstop
4:00 pm - 9:37 pmPWM-ORD
6h 37m1 stop
$247American Airlines
Find Deal
Wed, Jun 5 - Mon, Jun 10
4:46 pm - 12:52 amORD-PWM
7h 06m1 stop
7:42 am - 2:10 pmPWM-ORD
7h 28m1 stop
$255American Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
10:57 am - 2:20 pmORD-PWM
2h 23mnonstop
6:00 am - 7:46 amPWM-ORD
2h 46mnonstop
$276United Airlines
Find Deal
Sat, Aug 24 - Sat, Aug 31
6:03 pm - 9:33 pmORD-PWM
2h 30mnonstop
6:00 am - 7:49 amPWM-ORD
2h 49mnonstop
$282United Airlines
Find Deal
Wed, Jun 5 - Tue, Jun 11

Flights from Chicago to Portland - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Portland to help you find the cheapest flights, the best time to fly and much more.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Portland, Maine.
Our data shows that the cheapest route for a one-way flight from Chicago to Portland, Maine cost $52 and was between Chicago O'Hare Intl Airport and Portland, Maine. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $73.

What’s the cheapest day of the week to fly from Chicago to Portland?

The average price of all flights from Chicago to Portland, Maine clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Portland on a Tuesday and more expensive on a Friday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Portland, Maine, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Portland, Maine is April, where tickets cost $335 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $490 and $443 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Portland, Maine, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Portland, Maine, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 65 days before departure.

Which airlines provide the cheapest flights from Chicago to Portland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $49. KAYAK users also found Chicago to Portland round-trip flights on Frontier from $78 and on Delta from $218.

Which airlines fly non-stop between Chicago and Portland, Maine?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Portland, Maine.
There are 3 airlines that fly nonstop from Chicago to Portland, Maine. They are: Frontier, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $28 for a one-way flight. On average, the best prices for this route can be found at Frontier.

How many flights are there between Chicago and Portland, Maine per day?

Each day, there are between 4 and 6 nonstop flights that take off from Chicago and land in Portland, Maine, with an average flight time of 2h 28m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 32 flights. The most frequent day of departure is Tuesday, when 19% of all weekly flights depart. The fewest flights depart on a Friday.

Which cabin class options are there for flights between Chicago and Portland, Maine?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Portland take?

A direct flight to Portland will take on average 2h 20m to travel the 885 miles flying distance from Chicago.

What’s the earliest departure time from Chicago to Portland?

Early birds can take the earliest flight from Chicago at 8:20 am and will be landing in Portland, Maine at 11:54 am.

What’s the latest departure time from Chicago to Portland?

If you prefer to fly at night, the latest flight from Chicago to Portland, Maine jets off at 7:15 pm and lands at 10:43 pm.

Good to know

Low season

March

High season

July

Cheapest flight

$49
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

Are your dates flexible? Find out the best times to travel from Chicago to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Portland

  • What is the cheapest flight from Chicago to Portland, Maine?

    In the last 3 days, the lowest price for a flight from Chicago to Portland, Maine was $49 for a one-way ticket and $78 for a round-trip.

  • Do I need a passport to fly between Chicago and Portland?

    No, a passport isn't needed to fly from Chicago to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Portland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Portland (Portland). The cheapest flights are generally found on the Chicago O'Hare Airport to Portland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Portland?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago to Portland flight route.

  • Which aircraft models fly most regularly from Chicago to Portland?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago to Portland flight route.

  • Which airline alliances offer flights from Chicago to Portland?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Portland, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Portland?

    There are nonstop flights from Chicago to Portland on a daily basis.

  • Which is the best airline for flights from Chicago to Portland, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Delta and United Airlines. With an average price for the route of $312 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $414 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Chicago to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $129 or less one-way and $183 or less round-trip.

Prefer to fly non-stop from Chicago to Portland?

Find which airlines fly direct from Chicago to Portland, which days they fly and book direct flights.

Nonstop departures

Chicago to Portland

Monday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Tuesday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

Wednesday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Thursday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

Friday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Saturday

Air New Zealand, American Airlines, Qatar Airways, +2 more

Air New Zealand, American Airlines, +3 more

Sunday

Air New Zealand, American Airlines, Frontier, +3 more

Air New Zealand, American Airlines, +4 more

See more direct flights

Nonstop returns

Portland to Chicago

Monday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Tuesday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

Wednesday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Thursday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

Friday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Saturday

Air New Zealand, American Airlines, Emirates, +3 more

Air New Zealand, American Airlines, +4 more

Sunday

Air New Zealand, American Airlines, Emirates, +4 more

Air New Zealand, American Airlines, +5 more

See more direct flights
See more direct flights

Top 4 airlines serving from Chicago to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10838 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from Chicago to Portland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Portland found on KAYAK in the last 72 hours.
6/4Tue
nonstopFrontier
2h 20mORD-PWM
$49
6/23Sun
nonstopFrontier
2h 20mORD-PWM
$59
6/16Sun
nonstopFrontier
2h 20mORD-PWM
$60
7/16Tue
1 stopDelta
5h 28mORD-PWM
$104
6/25Tue
1 stopDelta
4h 36mMDW-PWM
$104
6/15Sat
nonstopAmerican Airlines
2h 28mORD-PWM
$120
6/15Sat
1 stopAmerican Airlines
7h 06mORD-PWM
$128
6/30Sun
1 stopSun Country Air
12h 56mORD-PWM
$150
5/31Fri
nonstopUnited Airlines
2h 30mORD-PWM
$214
5/7Tue
nonstopUnited Airlines
2h 34mORD-PWM
$215

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Last minute flights from Chicago to Portland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Portland that are departing in the next 10 days.
5/9Thu
multi-stopFrontier
17h 09mORD-PWM
5/14Tue
multi-stopFrontier
12h 53mPWM-ORD
$234
5/9Thu
multi-stopFrontier
17h 09mORD-PWM
5/12Sun
multi-stopFrontier
16h 19mPWM-ORD
$236
5/9Thu
multi-stopFrontier
17h 09mORD-PWM
5/13Mon
multi-stopFrontier
15h 32mPWM-ORD
$246
5/8Wed
multi-stopFrontier
26h 35mORD-PWM
5/16Thu
multi-stopFrontier
9h 48mPWM-ORD
$265
5/7Tue
multi-stopAmerican Airlines
4h 10mORD-PWM
5/11Sat
multi-stopAmerican Airlines
7h 35mPWM-ORD
$386
5/7Tue
multi-stopDelta
6h 55mORD-PWM
5/11Sat
multi-stopDelta
4h 59mPWM-ORD
$388
5/7Tue
multi-stopDelta
10h 26mORD-PWM
5/11Sat
multi-stopDelta
7h 02mPWM-ORD
$393
5/7Tue
nonstopUnited Airlines
2h 34mORD-PWM
5/11Sat
nonstopUnited Airlines
3h 03mPWM-ORD
$473
5/8Wed
multi-stopUnited Airlines
7h 13mORD-PWM
5/11Sat
nonstopUnited Airlines
3h 03mPWM-ORD
$482
5/5Sun
multi-stopAmerican Airlines
7h 59mORD-PWM
5/12Sun
multi-stopAmerican Airlines
6h 54mPWM-ORD
$626

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Flights to Portland

Destination:

Portland (PWM)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$750
$1,361
$599
$73