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 Wednesday or Tuesday and return on a Saturday

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 2021: 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
Precipitation
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

$129

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.
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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.

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.

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 Thursday. 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.

Cheap flights from Chicago to Portland in November, December 2021

The best prices found for CHI to PWM flights for November, December
4 Dec - 12 Dec
$165pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
7 Dec - 12 Dec
$172pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 12 Dec
$173pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Portland 2022 flight deals

Cheap flights to Portland from Chicago found for next year
4 Dec - 12 Dec
$165pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
7 Dec - 12 Dec
$172pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 12 Dec
$173pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Portland from Chicago

Save time with Chicago to Portland direct flight deals
14 Dec - 16 Dec
$194pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
22 Mar - 29 Mar
$269pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
15 Dec - 17 Dec
$291pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United 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
4 Dec - 12 Dec
$165pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 12 Dec
$173pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
PWM
Portland
PWM
Portland
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 12 Dec
$204pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
PWM
Portland
PWM
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Portland from Chicago

The cheapest one-way flights from Chicago to Portland
1:00 am - 12:13 pm
Delta
2 Stops
10h 13m
MDW - PWM
Delta
$129
Delta
12:59 am - 11:36 am
Frontier
1 Stop
9h 37m
ORD - PWM
Frontier
$141
Kiwi.com
12:55 am - 8:42 am
American Airlines
1 Stop
6h 47m
ORD - PWM
American Airlines

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 4 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 $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Portland, Maine for under $200. The cheapest flight booked recently is on Multiple Airlines for just $165, but on average you can expect to pay $212.

Are there nonstop flights from Chicago to Portland, Maine for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Portland, Maine under $200. A good price for a nonstop flight from Chicago to Portland, Maine is less than $405.

Are there last-minute flights available from Chicago to Portland, Maine for under $200?

There are currently 20+ open flights from Chicago to Portland, Maine within the next 7 days for less than $200.

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

American Airlines, at $172, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Frontier and United Airlines. American Airlines is 53% 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 $79 on United Airlines. Other airlines that offer cheap prices include Delta from $92 and American Airlines from $135 one-way.

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 United Airlines (86%), Air New Zealand (85%) or Air Wisconsin (84%) as they are the most reliable in getting you off to your destination on time.

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 $576, our data indicates the cheapest price to be $98. The most popular route (Chicago O'Hare Intl - Portland), is priced around $165.

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.

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 72 hours 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 72 hours 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 54m

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Portland

Top 3 airlines flying from Chicago to Portland

The chart below displays the airlines Cheapflights users traveling from Chicago to Portland choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Delta
$125 $421 No cancel fee N/A
American Airlines
$137 $302 No cancel fee 71%
United Airlines
$177 $384 No cancel fee 69%

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 53% of CHI to PWM departures
Afternoon Noon to 6 PM 46% of CHI to PWM departures
Early morning Midnight to 6 AM 1% 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
4 daily flights
Monday
4 daily flights
Tuesday
4 daily flights
Wednesday
5 daily flights
Thursday
3 daily flights
Friday
5 daily flights
Saturday
4 daily flights
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