Find the cheapest flights from Maine to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Delta flights from Maine to Chicago Midway Airport
Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Southwest flights from Maine to Chicago Midway Airport
Our best Southwest deals on Maine to Chicago Midway Airport flight tickets
momondo Fare Finder
Use the filters below to find and compare flights from 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 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 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 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 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 Maine to Chicago Midway flight route?
Fly from Portland to Chicago Midway for the best Maine - Chicago Midway flight prices
What cabin class options are available on Maine to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on 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.
How many flights depart from Maine to Chicago Midway Airport on average per week?
The number of flights available between Maine and Chicago Midway Airport is 3 per week as of October 2026. The most frequent departure day is Mon, with 33% of weekly flights leaving on this day.
How long does it take to fly to Chicago Midway Airport?
On average, it takes 2h 57m to fly from Maine to Chicago Midway Airport if you fly out of Portland (the most popular airport in Maine) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Bangor and into Chicago O'Hare Intl Airport, then the flight time is around 3h 17m.
Cheap Maine to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Maine to Chicago Midway Airport
Frequently asked questions about flying from Maine to Chicago Midway Airport
When did momondo last update prices for flights from Maine to Chicago Midway Airport?
Prices for flights from Maine to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Maine to Chicago Midway Airport?
There is 1 operator available for flights from Maine to Chicago Midway Airport as of October 2026.
How old do you have to be to fly from Maine to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Maine to Chicago Midway Airport?
Based on momondo bookings for flights between 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%.
Best airlines flying from Maine to Chicago Midway Airport
Compare and see reviews for airlines that fly from Maine to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $267 | Free Cancellation | Rating 7.9 4,228 reviews |
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 Maine to Chicago?
Finding the right flight to Chicago from Maine is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Maine to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Maine with this policy.
How can momondo help me find flights from Maine to Chicago?
Once you have performed a search for Maine to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Maine to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Maine. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.