Question 1

Which is the best airline for flights from Portland to Chicago, Southwest or United Airlines?

Accepted Answer

The two airlines most popular with KAYAK users for flights from Portland to Chicago are Southwest and United Airlines. With an average price for the route of $398 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $373 and an overall rating of 7.4.

Question 2

How long does a flight from Portland to Chicago take?

Accepted Answer

Direct flights cover the 885 miles separating Portland to Chicago in about 2h 30m.

Question 3

How many flights are there between Portland and Chicago per day?

Accepted Answer

Each day, there are 6 nonstop flights that take off from Portland and land in Chicago, with an average flight time of 2h 58m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 42 flights and there are the same amount of flights each day (6).

Question 4

How many flights are there between Portland and Chicago per day?

Accepted Answer

Each day, there are 6 nonstop flights that take off from Portland and land in Chicago, with an average flight time of 2h 58m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 42 flights and there are the same amount of flights each day (6).

Question 5

What is the cheapest flight from Portland to Chicago?

Accepted Answer

In the last 5 days, the lowest price for a flight from Portland to Chicago was $128 for a one-way ticket and $287 for a round-trip.

Question 6

Do I need a passport to fly between Portland and Chicago?

Accepted Answer

A passport is not required to fly from Portland to Chicago.

Question 7

Which airlines fly most frequently between Portland and Chicago?

Accepted Answer

Portland and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (21 flights per week), United Airlines (14 flights per week), and Southwest (7 flights per week).

Question 8

Which airlines fly most frequently between Portland and Chicago?

Accepted Answer

Portland and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (21 flights per week), United Airlines (14 flights per week), and Southwest (7 flights per week).

Question 9

What’s the cheapest day of the week to fly from Portland to Chicago?

Accepted Answer

Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Sunday. On your return trip to Portland, you should consider flying back on a Saturday, and avoid Sundays for better deals.

Question 10

What’s the cheapest day of the week to fly from Portland to Chicago?

Accepted Answer

Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Sunday. On your return trip to Portland, you should consider flying back on a Saturday, and avoid Sundays for better deals.

Question 11

Which airports will I be using when flying from Portland to Chicago?

Accepted Answer

On your way to Chicago, you’ll fly out from Portland. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

Question 12

What’s the earliest departure time from Portland to Chicago?

Accepted Answer

Early birds can take the earliest flight from Portland at 6:00 am and will be landing in Chicago at 8:11 am.

Question 13

What’s the latest departure time from Portland to Chicago?

Accepted Answer

If you prefer to fly at night, the latest flight from Portland to Chicago jets off at 7:34 pm and lands at 9:40 pm.

Question 14

Which airlines fly non-stop between Portland and Chicago?

Accepted Answer

There are 3 airlines that fly nonstop from Portland to Chicago. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at $209 for a round-trip flight. On average, the best prices for this route can be found at American Airlines.

Question 15

Which airlines fly non-stop between Portland and Chicago?

Accepted Answer

There are 3 airlines that fly nonstop from Portland to Chicago. They are: American Airlines, Southwest and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at $209 for a round-trip flight. On average, the best prices for this route can be found at American Airlines.

Question 16

Which airlines offer Wi-Fi service onboard planes from Portland to Chicago?

Accepted Answer

American Airlines, and Delta offer inflight Wi-Fi service on the Portland to Chicago flight route.

Question 17

Which aircraft models fly most regularly from Portland to Chicago?

Accepted Answer

The Embraer 175 is the aircraft model that flies most regularly on the Portland to Chicago flight route.

Question 18

Which airline alliances offer flights from Portland to Chicago?

Accepted Answer

SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Portland and Chicago, with SkyTeam being the most commonly used for this route.

Question 19

On which days can I fly direct from Portland to Chicago?

Accepted Answer

There are nonstop flights from Portland to Chicago on a daily basis.

Question 20

What is the cheapest month to fly from Portland to Chicago?

Accepted Answer

The cheapest month for flights from Portland to Chicago is September, where tickets cost $322 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $460 and $413 respectively.

Question 21

What is the cheapest month to fly from Portland to Chicago?

Accepted Answer

The cheapest month for flights from Portland to Chicago is September, where tickets cost $322 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $460 and $413 respectively.

Question 22

How does KAYAK find such low prices on flights from Portland to Chicago?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Chicago.

Question 23

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Chicago?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

Question 24

What is the Hacker Fare option on flights from Portland to Chicago?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Portland with another airline.

Question 25

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Chicago?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Question 26

What is the cheapest layover airport when flying from Portland to Chicago?

Accepted Answer

Flights via New York (JFK) offer the most affordable fares, with an average round-trip price of $185.

Question 27

What is the most popular layover airport when flying from Portland to Chicago?

Accepted Answer

Washington, D.C. (DCA) is the top choice – 27% of KAYAK users who clicked on 1-stop flights from Portland to Chicago picked an itinerary connecting there.

Question 28

Which layover airport has the quickest connection when flying from Portland to Chicago?

Accepted Answer

If you prefer a quick connection, Washington, D.C. (DCA) often has the shortest layovers from Portland to Chicago, with an average of 1h 01m.

Question 29

Which layover airport offers the shortest total travel time from Portland to Chicago?

Accepted Answer

Consider flying via Detroit (DTW) for the shortest journey. The average one-way travel time for flights connecting there is 5h 01m.

Question 30

Which cabin class options are there for flights between Portland and Chicago?

Accepted Answer

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 31

Which cabin class options are there for flights between Portland and Chicago?

Accepted Answer

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 32

Which airlines provide the cheapest flights from Portland to Chicago?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Portland to Chicago were found on JetBlue ($287) and Southwest ($287).

Question 33

Which airlines provide the cheapest flights from Portland to Chicago?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Portland to Chicago were found on JetBlue ($287) and Southwest ($287).

Question 34

What is the cheapest Portland to Chicago flight route?

Accepted Answer

The absolute cheapest return flight from Portland to Chicago costs $291 on the route between Portland (PWM) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Portland (PWM) and Chicago Midway Airport (MDW) were, on average, 9% cheaper than other Portland-Chicago routes. The most popular route is between Portland (PWM) and Chicago O'Hare Intl Airport (ORD).

Question 35

What is the cheapest Portland to Chicago flight route?

Accepted Answer

The absolute cheapest return flight from Portland to Chicago costs $291 on the route between Portland (PWM) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Portland (PWM) and Chicago Midway Airport (MDW) were, on average, 9% cheaper than other Portland-Chicago routes. The most popular route is between Portland (PWM) and Chicago O'Hare Intl Airport (ORD).

Question 36

How far in advance should I book a flight from Portland to Chicago?

Accepted Answer

To get a below average price on the flight from Portland to Chicago, you should book around 3 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Question 37

How far in advance should I book a flight from Portland to Chicago?

Accepted Answer

To get a below average price on the flight from Portland to Chicago, you should book around 3 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Question 38

Can I save money by flying with a layover from Portland to Chicago?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $340 on average.

Question 39

Can I save money by flying with a layover from Portland to Chicago?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $340 on average.

Question 40

How much is a round-trip flight from Portland, Maine to Chicago?

Accepted Answer

Flight prices are below average for this route right now.Flights to Chicago from Portland, Maine usually cost between $308 and $401 in August.
The lowest price found in the past 5 days was $287 on JetBlue (Aug 20-Aug 23).

Question 41

What are the most popular airlines flying to Chicago?

Accepted Answer

The most popular airline among KAYAK users flying to Chicago is American Airlines, followed by United Airlines and Delta.

Low season	January
High season	May
Cheapest flight	$133

PWM - CHI

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Everything you should know

Cheap Flights from Portland to Chicago (PWM-CHI)

Recent round-trip flight deals from Portland to Chicago

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KAYAK's insights & trends for Portland to Chicago flights

How much is a round-trip flight from Portland, Maine to Chicago?

What is the cheapest Portland to Chicago flight route?

What’s the cheapest day of the week to fly from Portland to Chicago?

What is the cheapest month to fly from Portland to Chicago?

Can I save money by flying with a layover from Portland to Chicago?

How far in advance should I book a flight from Portland to Chicago?

Which airlines provide the cheapest flights from Portland to Chicago?

Which airlines fly most frequently between Portland and Chicago?

Which airlines fly non-stop between Portland and Chicago?

What is the most popular layover airport when flying from Portland to Chicago?

What is the cheapest layover airport when flying from Portland to Chicago?

Which layover airport offers the shortest total travel time from Portland to Chicago?

Which layover airport has the quickest connection when flying from Portland to Chicago?

Which cabin class options are there for flights between Portland and Chicago?

How many flights are there between Portland and Chicago per day?

How long does a flight from Portland to Chicago take?

What’s the earliest departure time from Portland to Chicago?

What’s the latest departure time from Portland to Chicago?

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