Cheap flights from Portland (PWM) to Chicago (CHI) from $85
This is the cheapest one-way flight price, found on 10/1. Prices may vary by date and flight preferences.
The best prices from Portland to Chicago are usually found in September or October, booked 46 days in advance, depart on a Wednesday or Saturday and return on a Tuesday
How to find the cheapest flight from Portland (PWM) to Chicago (CHI)
All the information you need to plan the best PWM to CHI flight in 2023: compare Portland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
Popular in | April |
|---|---|
Cheapest in | September |
Round-trip from | $207 |
One-way from | $135 |
PWM - CHI Price | $207 - $364 |
|---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
What is the cheapest day to fly round-trip from Portland, Maine to Chicago?
Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.
How far in advance should I book a flight from Portland, Maine to Chicago?
Users have found that booking a flight from Portland, Maine to Chicago at least 43 days early can save you up to 33% on average compared to booking a flight this week. If booking 43 days before your flight isn’t an option for you, users have found flights from Portland, Maine to Chicago for as little as $470 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $508 for flights departing within the next 3 days.
What is the cheapest month to fly from Portland, Maine to Chicago?
The best pricing can be found in the month of September. Prices to Chicago from Portland, Maine average $394. You can even find prices in September for less than $394, as users have found deals to Chicago from as low as $203. The month of April appears to be one of the more expensive times to travel to Chicago from Portland, Maine. Flying in the targeted month can save you up to 28%.
When is the cheapest time to fly from Portland, Maine to Chicago (PWM - CHI)?
One of the essential ways to save on airfare from Portland, Maine to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 23% on airfare.
Cheap Delta flights from Portland to Chicago
Check out some of the cheapest Delta flights we've come across from Portland to Chicago. Make sure to double check the flight details before booking.
Cheap Frontier flights from Portland to Chicago
Some of the lowest-priced Frontier flights we've found at this time heading from Portland to Chicago. Deals are refreshing constantly so come back soon for more options.
Cheap Portland to Chicago flights in October & November 2023
The best prices found for PWM to CHI flights for October, November
The lowest fares we've come across on flights traveling from Portland to Chicago in October and November 2023. For more flight deals, be sure to check back very soon.
Portland to Chicago 2023 flight deals
Cheap flights to Chicago from Portland found for this year
The lowest fares we've come across on flights traveling from Portland to Chicago in October and November 2023. For more flight deals, be sure to check back very soon.
Non-stop flights to Chicago from Portland
Save time with Portland to Chicago direct flight deals
Take a look at some of the direct flights traveling from Portland to Chicago in the near future. Users can also choose from other Portland to Chicago flights by using the search form above.
Portland to Chicago flights leaving soon
Late deals on return flights to Chicago from Portland, departing today and this week
Users seeking a last-minute flight from Portland to Chicago should consider booking one of these fares. To prevent any unwanted surprises, users should verify their flight info before booking.
One-way flights to Chicago from Portland
The cheapest one-way flights from Portland to Chicago
Some of the best available deals we've found on one-way flights from Portland to Chicago. Users needing a return flight from Portland to Chicago should utilize the search form above.
Find flights from Portland to Chicago within your budget
Use the slider to find flights from Portland to Chicago that fit your budget.
Fly from
Fly to
Budget
$178 - $269
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Fri 11/3
1 stop25h 07m
Chicago O'Hare Intl
Sun 11/5
1 stop7h 05m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Fri 11/3
1 stop22h 06m
Chicago Midway
Sun 11/5
1 stop20h 54m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Thu 12/14
1 stop13h 50m
Chicago Midway
Mon 12/18
1 stop21h 47m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Tue 1/23
1 stop12h 25m
Chicago Midway
Mon 1/29
1 stop21h 56m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sat 10/14
1 stop9h 14m
Chicago O'Hare Intl
Tue 10/17
1 stop21h 45m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sat 10/21
1 stop8h 46m
Chicago O'Hare Intl
Mon 10/23
2 stops15h 08m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Tue 10/31
Nonstop2h 53m
Chicago O'Hare Intl
Wed 11/1
Nonstop2h 20m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Wed 1/24
1 stop8h 10m
Chicago O'Hare Intl
Tue 1/30
Nonstop2h 19m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Tue 10/31
1 stop4h 11m
Chicago Midway
Wed 11/1
1 stop7h 49m
Reviews of airlines servicing Chicago
Get a feel of what it's like to fly with Delta, Frontier and United Airlines from Portland to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
The flight was redirected while in flight and i understand why that could not be helped. HOWEVER, there were no instructions of what to expect while we were on the plane. That would have eliminated much angst with many passengers. The gate agents were really trying to answer questions….and one in particular was down right unaware of the feelings of the passengers. She did not listen to the questions, just kept repeating the same mantra….just being a little helpful would have gone a long way to calm people down. She literally could have made the experience much more tolerable. I wish i knew her name so you could help her understand the impact she had on several people, which spread throughout many passengers.
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
The flight was redirected while in flight and i understand why that could not be helped. HOWEVER, there were no instructions of what to expect while we were on the plane. That would have eliminated much angst with many passengers. The gate agents were really trying to answer questions….and one in particular was down right unaware of the feelings of the passengers. She did not listen to the questions, just kept repeating the same mantra….just being a little helpful would have gone a long way to calm people down. She literally could have made the experience much more tolerable. I wish i knew her name so you could help her understand the impact she had on several people, which spread throughout many passengers.
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
The flight was redirected while in flight and i understand why that could not be helped. HOWEVER, there were no instructions of what to expect while we were on the plane. That would have eliminated much angst with many passengers. The gate agents were really trying to answer questions….and one in particular was down right unaware of the feelings of the passengers. She did not listen to the questions, just kept repeating the same mantra….just being a little helpful would have gone a long way to calm people down. She literally could have made the experience much more tolerable. I wish i knew her name so you could help her understand the impact she had on several people, which spread throughout many passengers.
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
The flight was redirected while in flight and i understand why that could not be helped. HOWEVER, there were no instructions of what to expect while we were on the plane. That would have eliminated much angst with many passengers. The gate agents were really trying to answer questions….and one in particular was down right unaware of the feelings of the passengers. She did not listen to the questions, just kept repeating the same mantra….just being a little helpful would have gone a long way to calm people down. She literally could have made the experience much more tolerable. I wish i knew her name so you could help her understand the impact she had on several people, which spread throughout many passengers.
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
The flight was redirected while in flight and i understand why that could not be helped. HOWEVER, there were no instructions of what to expect while we were on the plane. That would have eliminated much angst with many passengers. The gate agents were really trying to answer questions….and one in particular was down right unaware of the feelings of the passengers. She did not listen to the questions, just kept repeating the same mantra….just being a little helpful would have gone a long way to calm people down. She literally could have made the experience much more tolerable. I wish i knew her name so you could help her understand the impact she had on several people, which spread throughout many passengers.
Related info for your journey
Useful info, stats and facts about Portland to Chicago flights.
What airport do you fly from for flights from Portland to Chicago?
For a flight from Portland to Chicago, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 4 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Portland on a regular basis.
Can I find flights from Portland, Maine to Chicago for under $200 on Cheapflights?
Yes, there are multiple flights from Portland, Maine to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $178, but on average you can expect to pay $214.
Are there nonstop flights from Portland, Maine to Chicago for under $300 on Cheapflights?
Cheapflights has at least 20 direct flights from Portland, Maine to Chicago under $300. A good price for a nonstop flight from Portland, Maine to Chicago is less than $381.
Are there last-minute flights available from Portland, Maine to Chicago for under $600?
There are currently 20+ open flights from Portland, Maine to Chicago within the next 7 days for less than $600.
What days are nonstop flights available from Portland, Maine to Chicago?
Nonstop flights can be found on the following days: Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.
How many flights depart from Portland, Maine to Chicago on average per day?
Per day, 5 flights depart from Portland, Maine to Chicago on average.
Early Morning (Midnight to 6am) - 80% of flight departures
Afternoon (Noon - 6pm) - 20% of flight departures
How long is the flight from Portland, Maine to Chicago?
For as low as $178, Frontier can have you in Chicago from Portland, Maine in 2h 53m. There are 902 mi between Portland, Maine and Chicago. This flight may include one or multiple stops.
What are the cheapest airlines flying from Portland, Maine to Chicago round-trip?
Cheapflights users have booked flights from Portland, Maine to Chicago round-trip from $178. Other airlines that can offer you cheap pricing are American Airlines, from $250, and United Airlines, from $260. These flights start at 54% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from Portland, Maine to Chicago one-way?
For one-way options, check prices for Frontier. According to our data, you can fly for as low as $85. Users have also found prices from $135 and $135 on American Airlines and Delta, respectively.
What are the most popular airlines that fly from Portland, Maine to Chicago?
The most popular airlines flying from Portland, Maine to Chicago are American Airlines, Delta and United Airlines. Something to consider prior to booking your flight.
What are the most reliable airlines from Portland, Maine to Chicago?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Chicago on time: Qatar Airways (90%), American Airlines (76%), Envoy Air (76%).
What are the cheapest flights from Portland, Maine to Chicago?
On average you can expect to pay $908 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $131 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $211.
What does PWM to ORD mean?
Great question - PWM to ORD just means Portland Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.
Other flights from Portland
Top 3 airlines flying from Portland to Chicago
The chart below displays the airlines Cheapflights users traveling from Portland to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Hourly flight availability from Portland to Chicago
See what time of day planes typically take off from Portland to Chicago
| 21%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 21%of flight departures | Morning6 am to noon |
| 58%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Weekly flight availability from Portland to Chicago
See how many times per day planes take to the skies headed from Portland to Chicago
| Sunday | 4daily flights |
|---|---|
| Monday | 4daily flights |
| Tuesday | 3daily flights |
| Wednesday | 4daily flights |
| Thursday | 4daily flights |
| Friday | 4daily flights |
| Saturday | 6daily flights |
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How does Cheapflights help users find flights from Portland to Chicago?
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Why should you use Cheapflights to find cheap flight tickets from Portland to Chicago?
Millions of users choose and trust Cheapflights to book the best flight deals from Portland to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.
Can Cheapflights find flights from Portland to Chicago with no change fees?
Certainly. Search results for flights to Chicago from Portland shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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Not ready to book yet? You can track prices for flights from Portland to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.