Popular in | April |
---|---|
Cheapest in | September |
Round-trip from | $208 |
One-way from | $89 |
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.
Users have found that booking a flight from Portland, Maine to Chicago at least 43 days early can save you up to 92% 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 $478 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 $539 for flights departing within the next 3 days.
The best pricing can be found in the month of September. Prices to Chicago from Portland, Maine average $384. You can even find prices in September for less than $384, as users have found deals to Chicago from as low as $166. 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 40%.
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 morning could potentially save you up to 12% on airfare.
Fly from
Fly to
Budget
$158 - $311
Route
Depart
Return
Price
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sun 1/21
1 stop15h 20m
Chicago O'Hare Intl
Tue 1/23
1 stop22h 31m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Sun 1/21
1 stop14h 24m
Chicago Midway
Wed 1/24
1 stop22h 00m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 1/11
1 stop13h 11m
Chicago O'Hare Intl
Mon 1/15
1 stop22h 28m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 1/11
1 stop8h 16m
Chicago O'Hare Intl
Sun 1/14
1 stop4h 44m
PortlandChicago Midway
PWM - MDW
PWMMDW
Portland
Sun 1/21
1 stop5h 01m
Chicago Midway
Tue 1/23
2 stops9h 57m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Wed 1/10
2 stops10h 15m
Chicago O'Hare Intl
Mon 1/15
2 stops8h 47m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Thu 1/11
2 stops8h 02m
Chicago O'Hare Intl
Sun 1/14
1 stop6h 23m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Sun 1/21
1 stop8h 10m
Chicago O'Hare Intl
Tue 1/23
Nonstop2h 15m
PortlandChicago O'Hare Intl
PWM - ORD
PWMORD
Portland
Wed 12/20
1 stop17h 18m
Chicago O'Hare Intl
Fri 5/10
1 stop17h 40m
Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $218). Flying from Portland, Maine to Chicago in June is currently the most expensive (average of $367). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$218
February
$229
March
$261
April
$293
May
$290
June
$367
July
$338
August
$274
September
$258
October
$248
November
$271
December
$257
Crew
Boarding
Comfort
Food
Entertainment
Overall
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.
Crew
Boarding
Comfort
Food
Entertainment
Overall
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.
Crew
Boarding
Comfort
Food
Entertainment
Overall
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.
Crew
Boarding
Comfort
Food
Entertainment
Overall
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.
Crew
Boarding
Comfort
Food
Entertainment
Overall
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.
CHI Temperature | 23 - 73.4 °F |
---|
CHI Rainfall | 1.7 - 4.9 inches |
---|
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.
Yes, there are multiple flights from Portland, Maine to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $158, but on average you can expect to pay $214.
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 $527.
There are currently 20+ open flights from Portland, Maine to Chicago within the next 7 days for less than $300.
Cheapflights users have booked flights from Portland, Maine to Chicago round-trip from $158. Other airlines that can offer you cheap pricing are American Airlines, from $207, and Delta, from $207. These flights start at 58% lower than the current average price 3 months from now.
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 $89 and $103 on American Airlines and Delta, respectively.
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.
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 (95%), American Airlines (94%), Envoy Air (94%).
On average you can expect to pay $679 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $153 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $183.
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.
50%of flight departures | Early morningMidnight to 6 am |
---|---|
0%of flight departures | Morning6 am to noon |
50%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Sunday | 4daily flights |
---|---|
Monday | 4daily flights |
Tuesday | 3daily flights |
Wednesday | 4daily flights |
Thursday | 4daily flights |
Friday | 4daily flights |
Saturday | 6daily flights |
Cheapflights helps you search for flights from Portland to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
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.
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.
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.