Cheap flights from Portland (PWM) to Chicago (CHI)

PWM — CHI
Sep 27 — Oct 41

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 inAprilHigh demand for flights, 22% potential price rise
Cheapest inSeptemberBest time to find cheap flights, 32% potential price drop
Round-trip from$269From Portland to Chicago (CHI)
One-way from$117One-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
Oct 26 - Oct 29
PWM

Portland

MDW

Chicago Midway

1 stop

4h 12m
MDW

Chicago Midway

PWM

Portland

1 stop

12h 50m
$214

Multiple Airlines

Pick Dates

Deal found 9/19/22

Oct 26 - Nov 1
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 48m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 34m
$218

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 26 - Oct 29
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

10h 40m
$224

Multiple Airlines

Pick Dates

Deal found 9/19/22

Portland to Chicago 2022 flight deals

Cheap flights to Chicago from Portland found for this year
Nov 5 - Nov 8
PWM

Portland

MDW

Chicago Midway

1 stop

13h 43m
MDW

Chicago Midway

PWM

Portland

1 stop

5h 34m
$204

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 26 - Oct 29
PWM

Portland

MDW

Chicago Midway

1 stop

4h 12m
MDW

Chicago Midway

PWM

Portland

1 stop

12h 50m
$214

Multiple Airlines

Pick Dates

Deal found 9/19/22

Oct 26 - Nov 1
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 48m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 34m
$218

Multiple Airlines

Pick Dates

Deal found 9/21/22

Cheap Delta flights from Portland to Chicago

Oct 26 - Oct 29
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

7h 18m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

4h 23m
$250

Delta

Pick Dates

Deal found 9/19/22

Nov 13 - Nov 16
PWM

Portland

MDW

Chicago Midway

1 stop

4h 17m
MDW

Chicago Midway

PWM

Portland

1 stop

4h 21m
$267

Delta

Pick Dates

Deal found 9/20/22

Oct 26 - Oct 29
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

7h 18m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

4h 23m
$271

Delta

Pick Dates

Deal found 9/21/22

Cheap United Airlines flights from Portland to Chicago

Oct 26 - Oct 29
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 19m
$228

United Airlines

Pick Dates

Deal found 9/19/22

Sep 30 - Oct 3
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

15h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

12h 54m
$244

United Airlines

Pick Dates

Deal found 9/19/22

Nov 1 - Nov 5
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

6h 32m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

7h 08m
$246

United Airlines

Pick Dates

Deal found 9/20/22

Non-stop flights to Chicago from Portland

Save time with Portland to Chicago direct flight deals
Oct 26 - Nov 1
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 48m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 34m
$218

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 26 - Oct 29
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 19m
$228

United Airlines

Pick Dates

Deal found 9/19/22

Oct 26 - Oct 31
PWM

Portland

ORD

Chicago O'Hare Intl

Nonstop

2h 48m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 34m
$249

Multiple Airlines

Pick Dates

Deal found 9/21/22

Last minute flights from Portland to Chicago

Late deals on return flights to Chicago from Portland, departing today and this week
Sep 30 - Oct 3
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

15h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

12h 54m
$244

United Airlines

Pick Dates

Deal found 9/19/22

Sep 30 - Oct 3
PWM

Portland

ORD

Chicago O'Hare Intl

2 stops

13h 58m
ORD

Chicago O'Hare Intl

PWM

Portland

1 stop

12h 54m
$253

United Airlines

Pick Dates

Deal found 9/19/22

Sep 30 - Oct 3
PWM

Portland

ORD

Chicago O'Hare Intl

1 stop

15h 56m
ORD

Chicago O'Hare Intl

PWM

Portland

Nonstop

2h 22m
$295

United Airlines

Pick Dates

Deal found 9/19/22

One-way flights to Chicago from Portland

The cheapest one-way flights from Portland to Chicago
Jan 4
PWM

Portland

MDW

Chicago Midway

1 stop

7h 51m
$80

Frontier

Pick Dates

Deal found 9/20/22

Oct 1
PWM

Portland

MDW

Chicago Midway

1 stop

15h 15m
$86

Frontier

Pick Dates

Deal found 9/22/22

Dec 16
PWM

Portland

MDW

Chicago Midway

1 stop

12h 37m
$96

Frontier

Pick Dates

Deal found 9/21/22

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 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.

Alternative routes for Portland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Peoriafrom $440 pp
Bangor to Peoriafrom $609 pp
Bangor to Molinefrom $1,246 pp

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
DeltaCheapest$152Average$340FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$162Average$352FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$170Average$410FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Portland to Chicago

See what time of day planes typically take off from Portland to Chicago
42%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
58%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
Sunday6daily flights
Monday7daily flights
Tuesday8daily flights
Wednesday8daily flights
Thursday7daily flights
Friday7daily flights
Saturday7daily flights