Cheap flights from Portland (PWM) to Chicago (CHI) from $85
This is the cheapest one-way flight price, found on 12/6. Prices may vary by date and flight preferences.
The best prices from Portland to Chicago are usually found in September or July, booked 86 days in advance, depart on a Saturday or Thursday and return on a Tuesday
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How to find the cheapest flight from Portland (PWM) to Chicago (CHI)
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 7, 2023.
Popular in | April |
|---|---|
Cheapest in | September |
Round-trip from | $208 |
One-way from | $89 |
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 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.
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 $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%.
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 morning could potentially save you up to 12% on airfare.
Cheap American Airlines flights from Portland to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Portland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
Check out some of the cheapest American Airlines flights we've come across from Portland to Chicago. Make sure to double check the flight details before booking.
Cheap Delta flights from Portland to Chicago
Explore cheap flight options specifically provided by Delta for the route between Portland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
Some of the lowest-priced Delta 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 December & January 2023
Find cheap flight options from Portland to Chicago specifically for the months of December and January 2023. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,618,515 searches. Prices were last updated on December 7, 2023.
The lowest fares we've come across on flights traveling from Portland to Chicago in December and January 2023. For more flight deals, be sure to check back very soon.
Portland to Chicago 2023 flight deals
Discover exclusive flight deals for travel between Portland and Chicago in 2023. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
The lowest fares we've come across on flights traveling from Portland to Chicago in December and January 2023. For more flight deals, be sure to check back very soon.
Non-stop flights to Chicago from Portland
Discover non-stop flight options from Portland to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
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
Find last-minute flight options from Portland to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
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
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
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
Customize your flight search to find flights from Portland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
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
Average price of flights to Chicago by month
Plan your trip from Portland to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Portland to Chicago is currently 107.33 USD while a round-trip flight costs 205.67 USD. Price data was last updated on December 3, 2023.
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
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 7, 2023.
Get a feel of what it's like to fly with American Airlines, Delta 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.
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.
Average temperature in Chicago by month
Plan your trip to Chicago by selecting the month that matches your preferred temperature. July sees the highest average temperature while January sees the lowest average temperature. Temperature data was last updated on December 3, 2023.
CHI Temperature | 23 - 73.4 °F |
|---|
Average rainfall in Chicago by month
Keep in mind the precipitation totals in Chicago when planning your trip. Chicago sees an average of 3.09 precipitation per year with the most occurring in August. Precipitation data was last updated on December 3, 2023.
CHI Rainfall | 1.7 - 4.9 inches |
|---|
Related info for your journey
Find useful and relevant information for your journey from Portland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 $158, 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 $527.
Are there last-minute flights available from Portland, Maine to Chicago for under $300?
There are currently 20+ open flights from Portland, Maine to Chicago within the next 7 days for less than $300.
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 $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.
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 $89 and $103 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 (95%), American Airlines (94%), Envoy Air (94%).
What are the cheapest flights from Portland, Maine to Chicago?
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.
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Portland to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Portland to Chicago
Discover the top 3 airlines that operate flights from Portland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,618,515 searches. Data last updated December 7, 2023.
Search flights to Chicago by cabin class
Hourly flight availability from Portland to Chicago
Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 7, 2023.
| 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 |
Weekly flight availability from Portland to Chicago
Explore weekly flight availability from Portland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 7, 2023.
| Sunday | 4daily flights |
|---|---|
| Monday | 4daily flights |
| Tuesday | 3daily flights |
| Wednesday | 4daily flights |
| Thursday | 4daily flights |
| Friday | 4daily flights |
| Saturday | 6daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Portland to Chicago?
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.
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.
Can Cheapflights notify me if prices for flights from Portland to Chicago become cheaper?
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.