Cheap flights from Chicago to Portland (CHI - PWM)

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The best prices from Chicago to Portland are usually found in August or July, booked 32 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

How to find the cheapest flight from
Chicago (CHI) to Portland (PWM)

All the information you need to plan the best CHI to PWM flight in 2022: compare Chicago to Portland flight prices with the expected peak season, weather and rainfall in Portland.
CHI - PWM
Price
$227 - $439
PWM
Temperature
23 - 68 °F
PWM
Rainfall
2.9 - 4.5 inches

Popular in

December

High demand for flights, 16% potential price rise

Cheapest in

August

Best time to find cheap flights, 39% potential price drop

Round-trip from

$227

From Chicago (CHI) to Portland

One-way from

$144

One-way flight from Chicago (CHI) to Portland

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Portland, Maine?

Flights from Chicago to Portland, Maine are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Portland, Maine.

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

August can be a great time to fly to Portland, Maine from Chicago with a flight ticket averaging about $144. Cheapflights users have found deals in the month of August for as cheap as $37. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from Chicago to Portland, Maine (CHI - PWM)?

One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 11% on airfare.

Cheap flights from Chicago to Portland in May, June 2022

The best prices found for CHI to PWM flights for May, June
23 May - 26 May
$170pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
23 May - 26 May
$199pp
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
19 May - 24 May
$220pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Portland 2022 flight deals

Cheap flights to Portland from Chicago found for this year
23 May - 26 May
$170pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
23 May - 26 May
$199pp
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
19 May - 24 May
$220pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Portland from Chicago

Save time with Chicago to Portland direct flight deals
27 Sep - 4 Oct
$280pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
29 Sep - 3 Oct
$300pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
9 Aug - 16 Aug
$302pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
PWM
Portland
PWM
Portland
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Portland

Late deals on round-trip flights to Portland from Chicago, departing today and this week
29 May - 4 Jun
$286pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
PWM
Portland
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 May - 4 Jun
$291pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
PWM
Portland
PWM
Portland
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
29 May - 4 Jun
$349pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Portland from Chicago

The cheapest one-way flights from Chicago to Portland
4:55 pm - 6:51 am
Sun Country Air
1 Stop
12h 56m
ORD - PWM
Sun Country Air
7:05 am - 8:21 am
Multiple Airlines
2 Stops
24h 16m
ORD - PWM
Multiple Airlines
$167
Kiwi.com
5:39 am - 7:46 am
Frontier
2 Stops
25h 07m
MDW - PWM
Frontier
$177
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Portland</span> flights.

Flight FAQs

From Chicago to Portland

What airport do you fly into for flights to Portland from Chicago?

Most people fly into Portland (PWM) if they book a flight to Portland from Chicago. On average, Portland has 5 inbound flights from Chicago per day from 5 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

Which airlines flying from Chicago to Portland have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Portland, Maine for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Portland, Maine for under $300. The cheapest flight booked recently is on Frontier for just $254, but on average you can expect to pay $283.

Are there nonstop flights from Chicago to Portland, Maine for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Portland, Maine under $300. A good price for a nonstop flight from Chicago to Portland, Maine is less than $342.

Are there last-minute flights available from Chicago to Portland, Maine for under $300?

There are currently 20+ open flights from Chicago to Portland, Maine within the next 7 days for less than $300.

What days are nonstop flights available from Chicago to Portland, Maine?

Nonstop flights are available for this route on the following days: Friday.

How many flights depart from Chicago to Portland, Maine on average per day?

On average, you can expect to see 2 flights from Chicago to Portland, Maine a day.
Evening (6pm - Midnight) - 100% of flight departures

How long is the flight from Chicago to Portland, Maine?

There are many flights that can get you from Chicago to Portland, Maine in 2h 17m. Fly via Frontier, Sun Country Air, or American Airlines to get the fastest option. There are 902 mi between Chicago and Portland, Maine. This flight may include one or multiple stops.

What are the cheapest airlines flying from Chicago to Portland, Maine round-trip?

Frontier, at $254, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Sun Country Air and American Airlines. Frontier is 31% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Chicago to Portland, Maine one-way?

One-way options have recently been found by users for as low as $124 on Frontier. Other airlines that offer cheap prices include American Airlines from $140 and Sun Country Air from $144 one-way.

What are the most popular airlines that fly from Chicago to Portland, Maine?

When booking a flight from Chicago to Portland, Maine, you may want to consider flying on American Airlines, JetBlue or Delta as they are the most popular for this route.

What are the cheapest flights from Chicago to Portland, Maine?

Looking for the cheapest flight from Chicago to Portland, Maine? While on average our users pay $412, our data indicates the cheapest price to be $85. The most popular route (Chicago O'Hare Intl - Portland), is priced around $259.

What are the most reliable airlines from Chicago to Portland, Maine?

No one likes to see their flight delayed. When booking a flight from Chicago to Portland, Maine consider choosing SkyWest Airlines (88%), Air Wisconsin (81%) or Air New Zealand (80%) as they are the most reliable in getting you off to your destination on time.

COVID Restrictions

View COVID Travel Restrictions for Portland, ME

Do I need a COVID test to fly to Portland from Chicago?

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

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Portland.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Portland.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Portland.

Do I need a test to fly back to Chicago from Portland?

Returning to Chicago from Portland

COVID-19 testing requirements
Visitors from Portland must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago.

Quarantine requirements
Visitors from Portland are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Portland, ME

Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Portland

Things to know before you go - useful duration and weather info for your trip from Chicago to Portland.
Flight duration from Chicago to PWM
2h 32m

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Portland

Hourly flight availability from Chicago to Portland

See what time of day planes typically take off from Chicago towards Portland.
Morning 6 AM to noon 70% of CHI to PWM departures
Afternoon Noon to 6 PM 30% of CHI to PWM departures
Early morning Midnight to 6 AM 0% of CHI to PWM departures
Evening 6 PM to midnight 0% of CHI to PWM departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Portland
See how many times per day planes take to the skies headed from Chicago to Portland.
Sunday
6 daily flights
Monday
6 daily flights
Tuesday
6 daily flights
Wednesday
6 daily flights
Thursday
6 daily flights
Friday
6 daily flights
Saturday
4 daily flights
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