Chicago

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
Feb 9 - Feb 11
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

9h 21m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

12h 31m
$194

United Airlines

View Deal

Deal found 1/24/22

Feb 9 - Feb 11
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

10h 50m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

9h 02m
$198

United Airlines

View Deal

Deal found 1/24/22

Feb 9 - Feb 11
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

10h 50m
ORD

Chicago O'Hare Intl

PWM

Portland

2 stops

11h 48m
$203

United Airlines

View Deal

Deal found 1/24/22

Portland to Chicago 2022 flight deals

Cheap flights to Chicago from Portland found for this year
Apr 29 - May 3
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 23m
$158

United Airlines

View Deal

Deal found 1/24/22

Apr 28 - May 3
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

5h 13m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 23m
$167

United Airlines

View Deal

Deal found 1/22/22

Apr 30 - May 3
PWM

Portland

MDW

Chicago Midway

1 stop

4h 11m
MDW

Chicago Midway

PWM

Portland

1 stop

3h 50m
$176

Delta

View Deal

Deal found 1/24/22

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
Apr 29 - May 3
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 23m
$158

United Airlines

View Deal

Deal found 1/24/22

Apr 29 - May 2
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 26m
$188

United Airlines

View Deal

Deal found 1/24/22

May 20 - May 23
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 57m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 27m
$214

United Airlines

View Deal

Deal found 1/23/22

Last minute flights from Portland to Chicago

Late deals on return flights to Chicago from Portland, departing today and this week
Feb 3 - Feb 6
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

13h 55m
ORD

Chicago O'Hare Intl

PWM

Portland

2 stops

27h 05m
$256

Multiple Airlines

View Deal

Deal found 1/23/22

Feb 4 - Feb 6
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

11h 51m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

8h 08m
$258

Multiple Airlines

View Deal

Deal found 1/22/22

Feb 4 - Feb 6
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

9h 46m
ORD

Chicago O'Hare Intl

PWM

Portland

2 stops

30h 16m
$265

Multiple Airlines

View Deal

Deal found 1/22/22

One-way flights to Chicago All airports from Portland

The cheapest one-way flights from Portland to Chicago
May 21
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

5h 07m
$87

American Airlines

View Deal

Deal found 1/23/22

Apr 25
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

7h 36m
$88

United Airlines

View Deal

Deal found 1/23/22

May 7
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

12h 08m
$93

Delta

View Deal

Deal found 1/25/22

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.

Can I fly to Chicago from Portland right now?

Information is based on travel restrictions for travel to Chicago within the United States

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?

Returning 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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Delta
Cheapest$105
Average$351
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety
American Airlines
Cheapest$144
Average$348
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
United Airlines
Cheapest$199
Average$405
FlexibilityNo cancel fee
On-time69%
COVID-19 safety

Hourly flight availability from Portland to Chicago

See what time of day planes typically take off from Portland to Chicago
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Portland to Chicago

See how many times per day planes take to the skies headed from Portland to Chicago
Sunday2daily flights
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday2daily flights
Friday2daily flights
Saturday2daily flights