Cheap flights from Portland, Maine to Chicago O'Hare Intl Airport from $73

Round-trip
1 adult
Economy
From?
To?
Tue 10/26
Tue 11/2

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Portland to Chicago O'Hare Intl Airport.
View current United States travel restrictions

Flight information for Portland, Maine to Chicago O'Hare Intl Airport
(PWM to ORD)

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago O'Hare Intl Airport
Best Price Found$249The best flight deal from Portland, Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $249
Fastest flight time2h 59mThe fastest flight from Portland, Maine to Chicago O'Hare Intl Airport takes 2h 59m
Direct flightsSunDirect flights go from Portland, Maine to Chicago O'Hare Intl Airport on Sunday. The only airline offering direct flights is American Airlines.

How to get the cheapest flight ticket from Portland, Maine to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Portland, Maine to Chicago O'Hare Intl Airport?

August

The cheapest time of year to fly to Chicago O'Hare Intl Airport from Portland, Maine is August. Most expensive is February

What is the cheapest airline that flies to Chicago O'Hare Intl Airport from Portland, Maine?

Delta

American Airlines, Delta, and United Airlines are the most popular carriers operating from Portland, Maine to Chicago O'Hare Intl Airport

How far in advance should you book Portland, Maine to Chicago O'Hare Intl Airport flights?

13 days before

The cheapest time to buy a flight from Portland, Maine to Chicago O'Hare Intl Airport is approximately 13 days to departure


Easily compare round-trip flights from Portland, Maine to Chicago O'Hare Intl Airport

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Portland, Maine to Chicago O'Hare Intl Airport by changing tabs
Multiple Airlines
Nov 19
PWM6:29 amPortland
10h 36m
1 stop
ORD5:05 pmChicago O'Hare Intl
Nov 22
ORD1:15 amChicago O'Hare Intl
11h 51m
1 stop
PWM1:06 pmPortland
Frontier
Nov 12
PWM6:19 amPortland
9h 47m
1 stop
ORD4:06 pmChicago O'Hare Intl
Nov 14
ORD1:00 amChicago O'Hare Intl
27h 34m
1 stop
PWM4:34 amPortland
United Airlines
Dec 4
PWM10:47 amPortland
3h 13m
ORD2:00 pmChicago O'Hare Intl
Dec 6
ORD1:00 pmChicago O'Hare Intl
2h 35m
PWM3:35 pmPortland
American Airlines
Nov 13
PWM12:38 amPortland
6h 22m
1 stop
ORD7:00 amChicago O'Hare Intl
Nov 16
ORD1:14 amChicago O'Hare Intl
6h 25m
1 stop
PWM7:39 amPortland
Multiple Airlines
Nov 16
PWM3:34 pmPortland
13h 56m
1 stop
ORD5:30 amChicago O'Hare Intl
Nov 23
ORD1:15 amChicago O'Hare Intl
28h 27m
1 stop
PWM5:42 amPortland
Multiple Airlines
Nov 18
PWM3:34 pmPortland
13h 56m
1 stop
ORD5:30 amChicago O'Hare Intl
Nov 22
ORD1:15 amChicago O'Hare Intl
11h 51m
1 stop
PWM1:06 pmPortland

Find the cheapest one-way flights from Portland, Maine to Chicago O'Hare Intl Airport

If you're looking for one-way flights from Portland, Maine to Chicago O'Hare Intl Airport, view some of our deals below provided by Frontier and United Airlines
Multiple Airlines
Nov 22
PWM2:51 pmPortland
27h 51m
1 stop
ORD6:42 pmChicago O'Hare Intl
Frontier
Jan 18
PWM6:00 amPortland
14h 24m
1 stop
ORD8:24 pmChicago O'Hare Intl
United Airlines
Nov 25
PWM1:10 amPortland
7h 57m
1 stop
ORD9:07 amChicago O'Hare Intl

Search last-minute flights to Chicago O'Hare Intl Airport from Portland, Maine

Find and compare flight prices for your last-minute flight from Portland, Maine to Chicago O'Hare Intl Airport
Multiple Airlines
Oct 30
PWM4:13 pmPortland
27h 26m
2 stops
ORD7:39 pmChicago O'Hare Intl
Nov 1
ORD3:24 amChicago O'Hare Intl
7h 55m
1 stop
PWM11:19 amPortland
Frontier
Oct 30
PWM4:13 pmPortland
27h 26m
2 stops
ORD7:39 pmChicago O'Hare Intl
Nov 7
ORD1:00 amChicago O'Hare Intl
27h 34m
1 stop
PWM3:34 amPortland
United Airlines
Oct 30
PWM12:45 pmPortland
2h 55m
ORD3:40 pmChicago O'Hare Intl
Nov 9
ORD6:15 amChicago O'Hare Intl
2h 30m
PWM8:45 amPortland
American Airlines
Oct 30
PWM10:00 amPortland
2h 51m
ORD12:51 pmChicago O'Hare Intl
Nov 4
ORD2:14 amChicago O'Hare Intl
6h 25m
1 stop
PWM8:39 amPortland
Delta
Oct 28
PWM3:05 amPortland
9h 03m
1 stop
ORD12:08 pmChicago O'Hare Intl
Nov 6
ORD7:00 amChicago O'Hare Intl
5h 54m
1 stop
PWM12:54 pmPortland
Multiple Airlines
Oct 30
PWM4:13 pmPortland
27h 26m
2 stops
ORD7:39 pmChicago O'Hare Intl
Nov 4
ORD3:24 amChicago O'Hare Intl
10h 14m
1 stop
PWM1:38 pmPortland

Best airlines flying from Portland, Maine to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Portland, Maine to Chicago O'Hare Intl Airport with momondo
AirlineRatingFree CancellationPrice
Delta
PriceFrom $105
Free Cancellation
Rating
8.2
8.2

Boarding

8.4

Comfort

8.3

Crew

8.1

Entertainment

8.0

Food

Reviews

Great

1 / 10
American Airlines
PriceFrom $144
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
United Airlines
PriceFrom $199
Free Cancellation
Rating
6.9
7.3

Boarding

6.7

Comfort

7.5

Crew

6.7

Entertainment

6.2

Food

Reviews

Thank you for making our honeymoon start amazing

1 / 10

  • Are airlines flying from Portland to Chicago O'Hare Intl offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Portland to Chicago O'Hare Intl are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, American Airlines, and Delta. You can search for the full list of airlines like United Airlines that are offering this flexibility.

  • How far is Portland to Chicago O'Hare Intl by plane?

    There are 899.6 mi between Portland and Chicago O'Hare Intl. A reasonable flight in good conditions will take 3h 13m.


Can I fly to Chicago O'Hare Intl from Portland right now?

Information is based on travel restrictions for travel to Chicago O'Hare Intl within the United States

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

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 O'Hare Intl.

Quarantine requirements
Visitors from Portland are not required to quarantine after entering Chicago O'Hare Intl.

Can I fly back to Portland from Chicago O'Hare Intl?

Returning to Portland from Chicago O'Hare Intl

COVID-19 testing requirements
Visitors from Chicago O'Hare Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Portland.

Quarantine requirements
Visitors from Chicago O'Hare Intl are not required to quarantine after entering Portland.

If you are planning to travel to Chicago O'Hare Intl Airport at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for Portland, Maine to Chicago O'Hare Intl Airport

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Portland, Maine to Chicago Midway Airport Flights
Fastest flight time5h 38m
Cheapest price$259