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CHI - PWM

Find cheap flights from Chicago to Portland from $40

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 6/25. 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
Fri 6/7
Fri 6/14

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 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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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
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
10:05 pm - 11:48 pmPWM-ORD
2h 43mnonstop
$100Frontier
Find Deal
Thu, Jun 6 - Sun, Jun 9
6:02 pm - 9:22 pmORD-PWM
2h 20mnonstop
10:12 pm - 11:58 pmPWM-ORD
2h 46mnonstop
$109Frontier
Find Deal
Tue, May 28 - Thu, May 30
6:00 pm - 9:21 pmORD-PWM
2h 21mnonstop
1:40 pm - 11:29 amPWM-ORD
22h 49m1 stop
Tue, Jul 23 - Fri, Jul 26
1:25 pm - 11:00 pmORD-PWM
8h 35m2 stops
5:05 am - 10:15 amPWM-ORD
6h 10m1 stop
$201Delta
Find Deal
Tue, Jun 11 - Tue, Jun 18
1:25 pm - 11:00 pmORD-PWM
8h 35m2 stops
11:30 am - 6:44 pmPWM-ORD
8h 14m2 stops
$206Delta
Find Deal
Tue, Jun 11 - Tue, Jun 18
5:52 pm - 9:12 pmORD-PWM
2h 20mnonstop
1:40 pm - 7:10 pmPWM-ORD
6h 30m1 stop
Thu, Jul 4 - Mon, Jul 8
7:15 pm - 10:43 pmORD-PWM
2h 28mnonstop
7:17 am - 9:10 amPWM-ORD
2h 53mnonstop
$214American Airlines
Find Deal
Sat, Jun 8 - Wed, Jun 12
5:27 am - 12:09 pmORD-PWM
5h 42m1 stop
7:18 am - 9:08 amPWM-ORD
2h 50mnonstop
$222American Airlines
Find Deal
Tue, Aug 6 - Wed, Aug 14
6:03 pm - 9:33 pmORD-PWM
2h 30mnonstop
5:30 am - 9:43 amPWM-ORD
5h 13m1 stop
$224United Airlines
Find Deal
Tue, Jun 11 - Wed, Jun 12
6:03 pm - 9:33 pmORD-PWM
2h 30mnonstop
6:00 am - 7:49 amPWM-ORD
2h 49mnonstop
$237United Airlines
Find Deal
Tue, Jun 11 - Sat, Jun 15

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 $49 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 $78.

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 Mondays 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 January, where tickets cost $313 on average. On the other hand, the most expensive months are December and April, where the average cost of tickets is $527 and $500 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 10 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 $40. KAYAK users also found Chicago to Portland round-trip flights on Frontier from $100 and on Delta from $201.

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 4 airlines that fly nonstop from Chicago to Portland, Maine. They are: American Airlines, 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 6 and 9 nonstop flights that take off from Chicago and land in Portland, Maine, with an average flight time of 2h 27m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 53 flights. The most frequent day of departure is Thursday, when 17% of all weekly flights depart. The fewest flights depart on a Monday.

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

January

High season

July

Cheapest flight

$40
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 6% 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 $40 for a one-way ticket and $100 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 $418 and an overall rating of 7.4.

  • 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 $79 or less one-way and $139 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 10789 reviews
8.2Boarding
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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.

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.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

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.

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.
6/25Tue
nonstopFrontier
2h 20mORD-PWM
$40
6/4Tue
nonstopFrontier
2h 20mORD-PWM
$49
6/25Tue
1 stopDelta
4h 36mMDW-PWM
$98
6/11Tue
2 stopsDelta
8h 35mORD-PWM
$103
6/16Sun
1 stopSun Country Air
4h 59mORD-PWM
$113
6/28Fri
nonstopAmerican Airlines
2h 34mORD-PWM
$120
6/15Sat
1 stopAmerican Airlines
5h 27mORD-PWM
$128
6/26Wed
1 stopSun Country Air
15h 23mORD-PWM
$130
6/3Mon
nonstopUnited Airlines
2h 30mORD-PWM
$229
5/27Mon
nonstopUnited Airlines
2h 26mORD-PWM
$289

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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.
5/10Fri
multi-stopDelta
4h 57mMDW-PWM
5/14Tue
multi-stopDelta
5h 06mPWM-MDW
$388
5/10Fri
multi-stopDelta
5h 21mORD-PWM
5/14Tue
multi-stopDelta
6h 04mPWM-ORD
$426
5/10Fri
multi-stopDelta
5h 21mORD-PWM
5/14Tue
multi-stopDelta
10h 42mPWM-ORD
$431
5/10Fri
multi-stopDelta
4h 57mMDW-PWM
5/14Tue
multi-stopDelta
9h 35mPWM-MDW
$438
5/10Fri
multi-stopDelta
8h 18mORD-PWM
5/14Tue
multi-stopDelta
10h 42mPWM-ORD
$508
5/10Fri
nonstopUnited Airlines
2h 34mORD-PWM
5/14Tue
nonstopUnited Airlines
3h 03mPWM-ORD
$518
5/10Fri
nonstopUnited Airlines
2h 34mORD-PWM
5/14Tue
multi-stopUnited Airlines
6h 35mPWM-ORD
$527
5/10Fri
multi-stopAmerican Airlines
5h 46mORD-PWM
5/10Fri
multi-stopAmerican Airlines
5h 24mPWM-ORD
$588
5/10Fri
multi-stopUnited Airlines
5h 11mORD-PWM
5/10Fri
nonstopUnited Airlines
3h 03mPWM-ORD
$608
5/10Fri
multi-stopUnited Airlines
7h 59mORD-PWM
5/10Fri
multi-stopUnited Airlines
6h 00mPWM-ORD
$743

Search by stops

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Search by price

Flights to Portland

Destination:

Portland (PWM)United States

Return flight deals:

Portland - Chicago

Cabin classes:

$750
$1,361
$599
$78