Cheap flights from Portland to Chicago (PWM - CHI)
The best prices from Portland to Chicago are usually found in August or July, booked 60 days in advance, depart on a Saturday or Thursday and return on a Wednesday
How to find the cheapest flight from Portland to Chicago
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 | $191 - $409 |
CHI | Temperature | 23 - 73.4 °F |
CHI | Precipitation | 1.7 - 4.9 inches |
Popular in
April
High demand for flights, 12% potential price rise
Cheapest in
August
Best time to find cheap flights, 47% potential price drop
Round-trip from
$191
From Portland to Chicago (CHI)
One-way from
$143
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 August. Prices to Chicago from Portland, Maine average $146. You can even find prices in August for less than $146, as users have found deals to Chicago from as low as $34. The month of December 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 41%.
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 morning tend to be the most expensive. A flight in the evening could potentially save you up to 52% on airfare.
Cheap flights from Portland to Chicago in January, February 2022
The best prices found for PWM to CHI flights for January, February
Portland
Chicago O'Hare Intl
1 stop
9h 21mChicago O'Hare Intl
Portland
1 stop
12h 31mUnited Airlines
Portland
Chicago O'Hare Intl
2 stops
10h 50mChicago O'Hare Intl
Portland
1 stop
9h 02mUnited Airlines
Portland
Chicago O'Hare Intl
2 stops
10h 50mChicago O'Hare Intl
Portland
2 stops
11h 48mUnited Airlines
Portland to Chicago 2022 flight deals
Cheap flights to Chicago from Portland found for this year
Portland
Chicago O'Hare Intl
Nonstop
2h 56mChicago O'Hare Intl
Portland
Nonstop
2h 23mUnited Airlines
Portland
Chicago O'Hare Intl
1 stop
5h 13mChicago O'Hare Intl
Portland
Nonstop
2h 23mUnited Airlines
Portland
Chicago Midway
1 stop
4h 11mChicago Midway
Portland
1 stop
3h 50mDelta
Non-stop flights to Chicago from Portland
Save time with Portland to Chicago direct flight deals
Portland
Chicago O'Hare Intl
Nonstop
2h 56mChicago O'Hare Intl
Portland
Nonstop
2h 23mUnited Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 56mChicago O'Hare Intl
Portland
Nonstop
2h 26mUnited Airlines
Portland
Chicago O'Hare Intl
Nonstop
2h 57mChicago O'Hare Intl
Portland
Nonstop
2h 27mUnited 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
13h 55mChicago O'Hare Intl
Portland
2 stops
27h 05mMultiple Airlines
Portland
Chicago O'Hare Intl
1 stop
11h 51mChicago O'Hare Intl
Portland
1 stop
8h 08mMultiple Airlines
Portland
Chicago O'Hare Intl
1 stop
9h 46mChicago O'Hare Intl
Portland
2 stops
30h 16mMultiple Airlines
One-way flights to Chicago All airports from Portland
The cheapest one-way flights from Portland to Chicago
Portland
Chicago O'Hare Intl
1 stop
5h 07mAmerican Airlines
Portland
Chicago O'Hare Intl
1 stop
7h 36mUnited Airlines
Portland
Chicago O'Hare Intl
2 stops
12h 08mDelta
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 2 outbound flights to Chicago per day. 5 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 $200 on Cheapflights?
Yes, there are multiple flights from Portland, Maine to Chicago for under $200. The cheapest flight booked recently is on United Airlines for just $158, but on average you can expect to pay $194.
Are there nonstop flights from Portland, Maine to Chicago for under $200 on Cheapflights?
Cheapflights has at least 20 direct flights from Portland, Maine to Chicago under $200. A good price for a nonstop flight from Portland, Maine to Chicago is less than $344.
Are there last-minute flights available from Portland, Maine to Chicago for under $300?
There are currently 11+ 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 Delta, from $176, and American Airlines, from $204. These flights start at 55% 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 American Airlines. According to our data, you can fly for as low as $87. Users have also found prices from $88 and $93 on United 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, 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 (95%), Air New Zealand (85%), United Airlines (81%).
What are the cheapest flights from Portland, Maine to Chicago?
On average you can expect to pay $362 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $98 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $176.
Other flights from Portland
Can I fly to Chicago from Portland right now?
Most visitors from Portland need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.
COVID-19 testing requirements
Visitors from Portland must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.
Quarantine requirements
Visitors from Portland are not required to quarantine after entering Chicago.
Can I fly back to Portland from Chicago?
COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Portland.
Quarantine requirements
Visitors from Chicago are not required to quarantine after entering 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
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 100%of flight departures | Morning6 am to noon |
| 0%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 | 2daily flights |
|---|---|
| Monday | 2daily flights |
| Tuesday | 2daily flights |
| Wednesday | 2daily flights |
| Thursday | 2daily flights |
| Friday | 2daily flights |
| Saturday | 2daily flights |