Cheap flights from Portland (PWM) to Chicago (CHI)
The best prices from Portland to Chicago are usually found in September or October, booked 60 days in advance, depart on a Thursday 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 2022: compare Portland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
PWM - CHI Price | $269 - $507 |
|---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
| Popular in | April | High demand for flights, 22% potential price rise |
|---|---|---|
| Cheapest in | September | Best time to find cheap flights, 32% potential price drop |
| Round-trip from | $269 | From Portland to Chicago (CHI) |
| One-way from | $117 | One-way flight from Portland to Chicago (CHI) |
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.
What is the cheapest month to fly from Portland, Maine to Chicago?
The best pricing can be found in the month of January. Prices to Chicago from Portland, Maine average $218. You can even find prices in January for less than $218, as users have found deals to Chicago from as low as $97. The month of June 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 50%.
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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 10% on airfare.
Cheap flights from Portland to Chicago in September, October 2022
The best prices found for PWM to CHI flights for September, October
Portland
Chicago Midway
1 stop
4h 12mChicago Midway
Portland
1 stop
12h 50mMultiple Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 48mChicago O'Hare Intl
Portland
Nonstop
2h 34mMultiple Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Portland
1 stop
10h 40mMultiple Airlines
Portland to Chicago 2022 flight deals
Cheap flights to Chicago from Portland found for this year
Portland
Chicago Midway
1 stop
13h 43mChicago Midway
Portland
1 stop
5h 34mMultiple Airlines
Portland
Chicago Midway
1 stop
4h 12mChicago Midway
Portland
1 stop
12h 50mMultiple Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 48mChicago O'Hare Intl
Portland
Nonstop
2h 34mMultiple Airlines
Cheap Delta flights from Portland to Chicago
Portland
Chicago O'Hare Intl
2 stops
7h 18mChicago O'Hare Intl
Portland
1 stop
4h 23mDelta
Portland
Chicago Midway
1 stop
4h 17mChicago Midway
Portland
1 stop
4h 21mDelta
Portland
Chicago O'Hare Intl
2 stops
7h 18mChicago O'Hare Intl
Portland
1 stop
4h 23mDelta
Cheap United Airlines flights from Portland to Chicago
Portland
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Portland
Nonstop
2h 19mUnited Airlines
Portland
Chicago O'Hare Intl
1 stop
15h 56mChicago O'Hare Intl
Portland
1 stop
12h 54mUnited Airlines
Portland
Chicago O'Hare Intl
1 stop
6h 32mChicago O'Hare Intl
Portland
1 stop
7h 08mUnited Airlines
Non-stop flights to Chicago from Portland
Save time with Portland to Chicago direct flight deals
Portland
Chicago O'Hare Intl
Nonstop
2h 48mChicago O'Hare Intl
Portland
Nonstop
2h 34mMultiple Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 50mChicago O'Hare Intl
Portland
Nonstop
2h 19mUnited Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 48mChicago O'Hare Intl
Portland
Nonstop
2h 34mMultiple Airlines
Last minute flights from Portland to Chicago
Late deals on return flights to Chicago from Portland, departing today and this week
Portland
Chicago O'Hare Intl
1 stop
15h 56mChicago O'Hare Intl
Portland
1 stop
12h 54mUnited Airlines
Portland
Chicago O'Hare Intl
2 stops
13h 58mChicago O'Hare Intl
Portland
1 stop
12h 54mUnited Airlines
Portland
Chicago O'Hare Intl
1 stop
15h 56mChicago O'Hare Intl
Portland
Nonstop
2h 22mUnited Airlines
One-way flights to Chicago from Portland
The cheapest one-way flights from Portland to Chicago
Portland
Chicago Midway
1 stop
7h 51mFrontier
Portland
Chicago Midway
1 stop
15h 15mFrontier
Portland
Chicago Midway
1 stop
12h 37mFrontier
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 7 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Portland on a regular basis.
Which airlines flying from Portland to Chicago have flexible cancellations due to COVID-19?
Some of the carriers operating flights from Portland to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.
Can I find flights from Portland, Maine to Chicago for under $300 on Cheapflights?
Yes, there are multiple flights from Portland, Maine to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $204, but on average you can expect to pay $232.
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 $287.
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 $228. Another airline that can offer you cheap pricing is Delta. These flights start at 42% 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 $80. Users have also found prices from $109 and $117 on United Airlines and Sun Country Air, 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, JetBlue and Delta. 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: Air Wisconsin (85%), United Airlines (85%), Air New Zealand (84%).
What are the cheapest flights from Portland, Maine to Chicago?
On average you can expect to pay $464 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $105 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $224.
Other flights from Portland
Alternative routes for Portland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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
| 42%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 0%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 | 6daily flights |
|---|---|
| Monday | 7daily flights |
| Tuesday | 8daily flights |
| Wednesday | 8daily flights |
| Thursday | 7daily flights |
| Friday | 7daily flights |
| Saturday | 7daily flights |