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Not ready to book? to track prices.Southwest flights from Portland, Maine to Chicago Midway Airport
Our best Southwest deals on Portland, Maine to Chicago Midway Airport flight tickets
Delta flights from Portland, Maine to Chicago Midway Airport
Our best Delta deals on Portland, Maine to Chicago Midway Airport flight tickets
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Use the filters below to find and compare flights from Portland, Maine to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 11/7
1:00 pm-7:40 pm
1 stop7h 40m
Chicago Midway
Wed 11/11
6:00 am-12:10 pm
1 stop5h 10m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 11/12
5:10 pm-11:15 pm
1 stop7h 05m
Chicago Midway
Sun 11/15
5:05 am-10:30 am
1 stop4h 25m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 11/7
5:25 am-2:50 pm
2 stops10h 25m
Chicago Midway
Wed 11/11
6:00 am-12:10 pm
1 stop5h 10m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 11/25
5:20 pm-11:15 pm
1 stop6h 55m
Chicago Midway
Tue 12/1
6:00 am-2:45 pm
1 stop7h 45m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Fri 11/6
5:10 pm-10:45 pm
2 stops6h 35m
Chicago Midway
Mon 11/9
5:05 am-10:30 am
1 stop4h 25m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 11/12
5:10 pm-10:45 pm
2 stops6h 35m
Chicago Midway
Sun 11/15
5:05 am-10:30 am
1 stop4h 25m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 11/17
12:45 pm-6:04 pm
1 stop6h 19m
Chicago Midway
Sat 11/21
5:13 pm-11:31 pm
1 stop5h 18m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 11/24
1:25 pm-10:00 pm
2 stops9h 35m
Chicago Midway
Tue 12/1
6:00 am-2:45 pm
1 stop7h 45m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Fri 12/11
5:10 pm-10:40 pm
2 stops6h 30m
Chicago Midway
Tue 12/15
5:20 am-2:45 pm
2 stops8h 25m
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 11/17
6:27 am-4:18 pm
2 stops10h 51m
Chicago Midway
Sat 11/21
5:13 pm-11:31 pm
1 stop5h 18m
See travel insights to Chicago from
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 day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Portland, Maine. The lowest ticket price found for a Friday departure recently was $418. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Portland, Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $694.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Portland, Maine in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $474 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $494. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Portland to Chicago Midway flight route?
Fly from Portland to Chicago Midway for the best Portland - Chicago Midway flight prices
What cabin class options are available on Portland, Maine to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Portland, Maine to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Portland to Chicago Midway?
Southwest and Delta are the most popular carriers operating from Portland to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, JetBlue and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Portland, Maine according to our data. Southwest is the first choice among our users, with 92% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
When to book flights from Portland, Maine to Chicago Midway Airport
Cheap Portland, Maine to Chicago Midway Airport (PWM to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Chicago Midway Airport
Frequently asked questions about flying from Portland, Maine to Chicago Midway Airport
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 2h 35m by plane in normal conditions.
When did momondo last update prices for flights from Portland Airport to Chicago Midway Airport?
Prices for flights from Portland Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago Midway Airport?
The number of operators available for flights from Portland Airport to Chicago Midway Airport is 1 as of October 2026.
How old do you have to be to fly from Portland Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Portland, Maine to Chicago Midway Airport?
Based on momondo bookings for flights between Portland, Maine and Chicago Midway Airport, the leading plane model is Embraer 175, making up 15.04% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.27%, Boeing 737-800 with 12.39%, and Embraer 175 (Enhanced Winglets) with 11.50%.
What is the most popular airline from Portland, Maine to Chicago Midway Airport?
Based on momondo bookings for flights between Portland, Maine and Chicago Midway Airport, the leading airline is Southwest, making up 100% of the total bookings.
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
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $267 | Free Cancellation | Rating 7.9 4,228 reviews |
Southwest Flights From Portland, Maine to Chicago Midway Airport
Southwest flies from Portland, Maine to Chicago Midway Airport around 5 times per week, with 4,228 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Portland, Maine to Chicago Midway Airport in the last 72 hours was $267 (round-trip), much lower than the average airfare cost of $378 for Southwest flights on this route.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Portland to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Portland to Chicago with flexible booking policies on momondo?
Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Portland to Chicago?
Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Portland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.