Flights from Portland Airport PWM to Chicago Airport MDW
We've found the cheapest flights to Chicago
As flights from International Jetport to Midway are in low demand, many airliners do not offer a direct flight. There is in fact only one airliner who you can fly with which is Southwest Airlines. The flight time is approximately 2 Hours 30 Minutes.
The most expensive flight prices are typically at weekends and daytime flights. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. If it is possible, you should book your flights 2 or more months in advance as ticket prices will be substantially lower.
The time zone at Midway is different from International Jetport, so please be aware of this when making travel arrangements.
If you plan on flying to Midway Airport from International Jetport Airport you can pre-arrange your long or short term parking at International Jetport Airport.
If you are renting a car at Midway Airport it is recommended to fill up the fuel tank before returning the vehicle at the nearest fuel station to Midway Airport in order to avoid incurring additional costs. *Please check your rental agreement to understand the fuel policy for your vehicle.
Organise and book your choice of transport to International Jetport Airport:
- Private Transfers to International Jetport Airport
- Buses to International Jetport Airport
- Taxis to International Jetport Airport
- Train Services to/near International Jetport Airport
Ensure your arrival at Midway Airport is as stress-free as possible by pre-booking your onwards transport - booking early may also save you money:
- Compare car rental at Midway Airport
- Private transfers at Midway Airport
- Buses from Midway Airport
- Taxis from Midway Airport
- Train services at or near Midway Airport
You can also research and pre-book a hotel near Midway Airport
Below you will see all the airlines that fly from International Jetport (PWM) to Midway (MDW) and the number of flights they operate each day.

Airliner | Mo | Tu | We | Th | Fr | Sa | Su | First Flight | Last Flight | Flights |
---|---|---|---|---|---|---|---|---|---|---|
Southwest Airlines | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 18:55 | 19:55 | VIEW FLIGHTS |
Flights from International Jetport to Midway are very limited. Only Southwest Airlines operate flights, of which there is only 1 per week. The time of the departure for this flight is 18:55
If you would like more information on this flight the please visit the website for Southwest Airlines at www.southwest.com/?ref=southwestairlines.com. You will be able to find the latest availability, prices and make your booking online.
Flight times for the route are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

Day | Flight Times | Flights | ||||
---|---|---|---|---|---|---|
Monday | 19:40
| VIEW FLIGHTS | ||||
Tuesday | 18:55
| VIEW FLIGHTS | ||||
Wednesday | 18:55
| VIEW FLIGHTS | ||||
Thursday | 19:40
| VIEW FLIGHTS | ||||
Friday | 19:40
| VIEW FLIGHTS | ||||
Saturday | 19:10
| VIEW FLIGHTS | ||||
Sunday | 19:55
| VIEW FLIGHTS |
Other routes are also possible. Flying from a different airport may offer more convenient flight times, so below we have we have put a list of other routes that may well be suitable.

Route | Stops | Distance | Flying Time |
---|---|---|---|
Bedford Hanscom to Chicago Midway | 0 | 2 Hours 25 Minutes | |
Boston to Chicago Midway | 0 | 2 Hours 26 Minutes | |
Manchester boston Regional to Chicago Midway | 0 | 2 Hours 24 Minutes |
Before you book your flights make sure you your passport is valid and preferably has at least 6 months or more left before it expires. To renew your passport it can take several weeks to renew and with many airliners flights are not refundable.
Looking for the best car hire deals?
Search for the best vehicle hire in Portland Maine, United States
Flight Price FAQ - Portland (PWM) to Chicago (MDW)
Compare Flight Prices from PWM to MDW

Was your flight delayed or cancelled?
You may be eligible to receive up to 600 EUR compensation per person in your party.
Claim Now!Flight Info FAQ - Portland (PWM) to Chicago (MDW)
Alternative Airports in United States with Connections from Portland Jetport Airport
- airplanemode_active Portland Maine Airport to New York La Guardia 46 flights per week
- airplanemode_active Portland Maine Airport to Chicago OHare International 31 flights per week
- airplanemode_active Portland Maine Airport to Philadelphia International 29 flights per week
- airplanemode_active Portland Maine Airport to Atlanta 23 flights per week
- airplanemode_active Portland Maine Airport to Washington Ronald Reagan Washington National 21 flights per week
- airplanemode_active Portland Maine Airport to Newark 14 flights per week
- airplanemode_active Portland Maine Airport to Minneapolis St Paul International 10 flights per week
- airplanemode_active Portland Maine Airport to Nashville 7 flights per week
- airplanemode_active Portland Maine Airport to Dallas Fort Worth International 7 flights per week
- airplanemode_active Portland Maine Airport to White Plains 5 flights per week
- airplanemode_active Portland Maine Airport to Charleston AFB Municipal 4 flights per week
- airplanemode_active Portland Maine Airport to Pittsburgh 4 flights per week
- airplanemode_active Portland Maine Airport to New Haven 2 flights per week
- airplanemode_active Portland Maine Airport to Norfolk International 2 flights per week
- airplanemode_active Portland Maine Airport to Rutland 2 flights per week
- airplanemode_active Portland Maine Airport to Nantucket 1 flights per week
- airplanemode_active Portland Maine Airport to Cleveland Burke Lakefront 1 flights per week
- airplanemode_active Portland Maine Airport to Buffalo Niagara International 1 flights per week
- airplanemode_active Portland Maine Airport to New Bedford 1 flights per week
- airplanemode_active Portland Maine Airport to Florence 1 flights per week
- airplanemode_active Portland Maine Airport to Islip 1 flights per week
- airplanemode_active Portland Maine Airport to Manassas 1 flights per week
- airplanemode_active Portland Maine Airport to Oxford Waterbury oxford 1 flights per week
- airplanemode_active Portland Maine Airport to Rome Griffiss AFB 1 flights per week
- airplanemode_active Portland Maine Airport to Stuart 1 flights per week
- airplanemode_active Portland Maine Airport to Trenton Mercer 1 flights per week
- airplanemode_active Portland Maine Airport to Washington Dulles International 36 flights per week
- airplanemode_active Portland Maine Airport to Baltimore Washington International Thurgood Marshall 29 flights per week
- airplanemode_active Portland Maine Airport to New York John F Kennedy International 25 flights per week
- airplanemode_active Portland Maine Airport to Charlotte Douglas 22 flights per week
- airplanemode_active Portland Maine Airport to Detroit 14 flights per week
- airplanemode_active Portland Maine Airport to Teterboro 13 flights per week
- airplanemode_active Portland Maine Airport to Presque Isle 10 flights per week
- airplanemode_active Portland Maine Airport to Denver International 7 flights per week
- airplanemode_active Portland Maine Airport to Orlando International 6 flights per week
- airplanemode_active Portland Maine Airport to Boston 4 flights per week
- airplanemode_active Portland Maine Airport to Manchester boston Regional 4 flights per week
- airplanemode_active Portland Maine Airport to Port Columbus International 2 flights per week
- airplanemode_active Portland Maine Airport to Miami International 2 flights per week
- airplanemode_active Portland Maine Airport to Raleigh 2 flights per week
- airplanemode_active Portland Maine Airport to Tampa 2 flights per week
- airplanemode_active Portland Maine Airport to Bangor 1 flights per week
- airplanemode_active Portland Maine Airport to Berlin Municipal 1 flights per week
- airplanemode_active Portland Maine Airport to Dothan 1 flights per week
- airplanemode_active Portland Maine Airport to Fort Lauderdale hollywood International 1 flights per week
- airplanemode_active Portland Maine Airport to Westhampton 1 flights per week
- airplanemode_active Portland Maine Airport to Morristown Municipal 1 flights per week
- airplanemode_active Portland Maine Airport to Baltimore Glenn L Martin 1 flights per week
- airplanemode_active Portland Maine Airport to Chicago Pal Waukee 1 flights per week
- airplanemode_active Portland Maine Airport to San Jose Mineta San Jose International 1 flights per week
- airplanemode_active Portland Maine Airport to Syracuse 1 flights per week
Don't forget to book a rental car!
Search for the best vehicle rentals at Portland Jetport Airport
Useful Information about Portland Jetport Airport

See all the airport lounges, locations and opening times available at Portland Jetport Airport
View...
See all bars and restaurants at Portland Jetport Airport, including locations and if they are before or after check-in
View...
See all shops available at Portland Jetport Airport - plan your duty free shopping in advance
View...
Things to see and do in and around Portland, Maine in the United States of America
View...