Cheap flights from Portland, Maine to Chicago Midway Airport from $219

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 Midway Airport.
View current United States travel restrictions

Flight information for Portland, Maine to Chicago Midway Airport
(PWM to MDW)

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago Midway Airport
Best Price Found$259The best flight deal from Portland, Maine to Chicago Midway Airport found on momondo in the last 72 hours is $259
Fastest flight time6h 05mThe fastest flight from Portland, Maine to Chicago Midway Airport takes 6h 05m
Direct flightsNoneThere are no direct flights from Portland, Maine to Chicago Midway Airport. Popular non-direct route for this connection is Portland Airport - Chicago Midway Airport.

How to get the cheapest flight ticket from Portland, Maine to Chicago Midway 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 Midway Airport?

January

The cheapest time of year to fly to Chicago Midway Airport from Portland, Maine is January. Most expensive is June

What is the cheapest airline that flies to Chicago Midway Airport from Portland, Maine?

United Airlines

Delta and United Airlines are the most popular carriers operating from Portland, Maine to Chicago Midway Airport


Easily compare round-trip flights from Portland, Maine to Chicago Midway 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 Midway Airport by changing tabs
Delta
Nov 13
PWM1:40 amPortland
6h 18m
1 stop
MDW7:58 amChicago Midway
Nov 16
MDW4:27 amChicago Midway
6h 49m
1 stop
PWM11:16 amPortland
Delta
Dec 2
PWM1:00 amPortland
10h 41m
2 stops
MDW11:41 amChicago Midway
Dec 6
MDW4:33 amChicago Midway
6h 06m
1 stop
PWM10:39 amPortland
Delta
Nov 13
PWM1:25 amPortland
10h 16m
2 stops
MDW11:41 amChicago Midway
Nov 16
MDW1:30 amChicago Midway
9h 46m
2 stops
PWM11:16 amPortland
Delta
Dec 3
PWM1:00 amPortland
10h 41m
2 stops
MDW11:41 amChicago Midway
Dec 6
MDW4:33 amChicago Midway
6h 06m
1 stop
PWM10:39 amPortland
Delta
Dec 3
PWM1:00 amPortland
10h 41m
2 stops
MDW11:41 amChicago Midway
Dec 6
MDW8:40 amChicago Midway
8h 06m
2 stops
PWM4:46 pmPortland
Delta
Dec 2
PWM1:40 amPortland
6h 18m
1 stop
MDW7:58 amChicago Midway
Dec 6
MDW4:33 amChicago Midway
6h 06m
1 stop
PWM10:39 amPortland

Find the cheapest one-way flights from Portland, Maine to Chicago Midway Airport

If you're looking for one-way flights from Portland, Maine to Chicago Midway Airport, view some of our deals below provided by Delta
Delta
Nov 25
PWM1:00 amPortland
8h 03m
2 stops
MDW9:03 amChicago Midway
Multiple Airlines
Nov 25
PWM6:06 amPortland
44h 24m
3 stops
MDW2:30 amChicago Midway
Delta
Oct 28
PWM3:15 amPortland
5h 38m
1 stop
MDW8:53 amChicago Midway

Search last-minute flights to Chicago Midway Airport from Portland, Maine

Find and compare flight prices for your last-minute flight from Portland, Maine to Chicago Midway Airport
Delta
Oct 30
PWM3:15 amPortland
5h 38m
1 stop
MDW8:53 amChicago Midway
Nov 1
MDW9:52 amChicago Midway
8h 17m
2 stops
PWM6:09 pmPortland
Delta
Oct 29
PWM10:05 amPortland
10h 36m
2 stops
MDW8:41 pmChicago Midway
Nov 1
MDW9:52 amChicago Midway
8h 17m
2 stops
PWM6:09 pmPortland
Delta
Oct 29
PWM3:05 amPortland
7h 02m
2 stops
MDW10:07 amChicago Midway
Nov 6
MDW8:40 amChicago Midway
8h 09m
1 stop
PWM4:49 pmPortland
Delta
Oct 29
PWM7:05 amPortland
6h 05m
1 stop
MDW1:10 pmChicago Midway
Nov 1
MDW9:52 amChicago Midway
8h 17m
2 stops
PWM6:09 pmPortland
Delta
Oct 28
PWM3:15 amPortland
5h 38m
1 stop
MDW8:53 amChicago Midway
Oct 31
MDW5:25 amChicago Midway
6h 00m
1 stop
PWM11:25 amPortland
Delta
Oct 28
PWM3:05 amPortland
7h 02m
2 stops
MDW10:07 amChicago Midway
Oct 31
MDW5:25 amChicago Midway
6h 00m
1 stop
PWM11:25 amPortland

Best airlines flying from Portland, Maine to Chicago Midway Airport

Compare and see reviews for airlines that fly from Portland, Maine to Chicago Midway Airport with momondo
AirlineRatingFree CancellationPrice
United Airlines
PriceFrom $207
Free Cancellation
Rating
6.9
7.3

Boarding

6.7

Comfort

7.5

Crew

6.7

Entertainment

6.2

Food

Reviews

Had to change planes.

1 / 10
Delta
PriceFrom $292
Free Cancellation
Rating
8.2
8.2

Boarding

8.4

Comfort

8.3

Crew

8.1

Entertainment

8.0

Food

Reviews

Great

1 / 10

  • Are airlines flying from Portland to Chicago Midway offering flexible cancellation due to COVID-19?

    To ease the stress of booking flights, some of our airline partners flying from Portland to Chicago Midway are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: Delta and United Airlines.

  • How far is Portland to Chicago Midway by plane?

    The straight-line distance from Portland to Chicago Midway is 894.8 mi. Typically, this will take 6h 18m by plane in normal conditions.


Can I fly to Chicago Midway from Portland right now?

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

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

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 Midway.

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

Can I fly back to Portland from Chicago Midway?

Returning to Portland from Chicago Midway

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

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

If you are planning to travel to Chicago Midway 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 Midway 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 O'Hare Intl Airport Flights
Fastest flight time2h 56m
Cheapest price$155