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Find cheap flights from Chicago Midway Airport to Maine from $57

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Maine departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

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Best Maine Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Portland
Portland1 stop$169
Bangor
Bangor2 stops$283
Boston
Boston1 stop$121

Good to know

Cheapest flight

$57
Flight from Chicago Midway Airport to Portland

FAQs - booking Maine flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Maine?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Maine.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Maine?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Maine from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Maine?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Maine with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Maine?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Maine from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Maine

  • Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Maine

Need help choosing which airline to fly with from Midway to Maine? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10277 reviews
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Maine

Recent round-trip flight deals

8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/14Wed
1 stopFrontier
7h 37mBOS-MDW
$121
8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/17Sat
1 stopFrontier
7h 25mBOS-MDW
$122
8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/17Sat
1 stopFrontier
7h 25mBOS-MDW
$123
8/7Wed
1 stopFrontier
8h 58mMDW-BOS
8/12Mon
1 stopFrontier
8h 28mBOS-MDW
$125
9/24Tue
1 stopDelta
8h 08mMDW-PWM
9/29Sun
1 stopDelta
4h 03mPWM-MDW
$196
8/20Tue
1 stopDelta
8h 25mMDW-PWM
8/27Tue
2 stopsDelta
11h 06mPWM-MDW
$201
6/17Mon
nonstopSouthwest
2h 15mMDW-BOS
6/20Thu
nonstopSouthwest
2h 35mBOS-MDW
$212
6/17Mon
1 stopSouthwest
4h 30mMDW-BOS
6/20Thu
nonstopSouthwest
2h 35mBOS-MDW
$221
8/2Fri
1 stop
10h 47mMDW-BOS
8/5Mon
3 stops
13h 50mBOS-MDW
$381
8/2Fri
1 stop
10h 47mMDW-BOS
8/5Mon
2 stops
12h 52mBOS-MDW
$402

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Recent one-way flight deals

8/14Wed
1 stopFrontier
21h 41mMDW-PWM
$57
6/20Thu
1 stopFrontier
10h 25mMDW-BOS
$70
6/19Wed
1 stopFrontier
23h 00mMDW-PWM
$73
8/15Thu
1 stopDelta
5h 13mMDW-PWM
$98
7/1Mon
1 stopAllegiant Air
10h 15mMDW-BOS
$123
7/1Mon
1 stopAllegiant Air
10h 15mMDW-BOS
$125
8/14Wed
2 stopsDelta
11h 27mMDW-PWM
$129
7/1Mon
2 stops
16h 17mMDW-BOS
$141
6/24Mon
2 stops
20h 52mMDW-BOS
$151
6/21Fri
2 stopsSouthwest
8h 35mMDW-BOS
$192

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Last minute flights from Midway to Maine

Last minute flight, train and bus deals

6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/18Tue
multi-stopFrontier
9h 38mBOS-MDW
$158
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/17Mon
multi-stopFrontier
6h 49mBOS-MDW
$188
6/16Sun
nonstopSouthwest
2h 15mMDW-BOS
6/19Wed
nonstopSouthwest
2h 35mBOS-MDW
$272
6/16Sun
multi-stopSouthwest
7h 25mMDW-BOS
6/19Wed
nonstopSouthwest
2h 35mBOS-MDW
$281
6/15Sat
multi-stopDelta
5h 11mMDW-BOS
6/19Wed
multi-stopDelta
4h 28mBOS-MDW
$336
6/15Sat
multi-stopDelta
5h 11mMDW-BOS
6/18Tue
multi-stopDelta
4h 28mBOS-MDW
$354
6/14Fri
multi-stop
10h 15mMDW-BOS
6/18Tue
multi-stop
5h 57mBOS-MDW
$633
6/14Fri
multi-stop
18h 40mMDW-BOS
6/18Tue
multi-stop
5h 57mBOS-MDW
$776
6/14Fri
multi-stopPorter Airlines
9h 05mMDW-BOS
6/16Sun
multi-stopPorter Airlines
15h 02mBOS-MDW
$1,084
6/13Thu
multi-stopPorter Airlines
9h 05mMDW-BOS
6/16Sun
multi-stopPorter Airlines
15h 02mBOS-MDW
$1,087

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Chicago Midway Airport - Maine Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Maine - Chicago Midway Airport

Cabin classes: