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$54 Find cheap flights from Chicago Midway Airport to Maine

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 8/24. 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
sáb. 7/13
sáb. 7/20

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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$158
Bangor
Bangor2 stops$284
Boston
Boston1 stop$100

Good to know

Cheapest flight

$54
Flight from Chicago Midway Airport to Boston

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 4% 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 10000 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

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.

The bag drop process took longer than other airlines. The boarding and crew were good. The seats do not recline and have minimal padding. The snacks/drinks are for purchase only. The flight was on time with no issues. I would fly them again if the cost was significantly less.

Crew was excellent. Flight was overbooked No seat assignment until the last moment.

My flight was delayed then cancelled My elder parents were upstairs waiting for a spirit rep to bring them downstairs to where my sister waited for 2 hours. My elder parents are not able to walk . My dad was wet of urine from where he could not hold it .waiting for some spirit personnel to wheel chair them back down stairs to where my sister was waiting for them for two hours . That is not ok

Poor response to delay, getting on plane, off plane and back on again

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.

Online check-in was not user-friendly. Too many fees, not cost effective.

They wouldn’t let us on the flight even tho we were an hour early. No refund not even our bags that were prepaid

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

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.

Book cheap flights from Chicago to Maine

Recent round-trip flight deals

8/28mié.
1 stopFrontier
10h 26mMDW-BOS
8/31sáb.
1 stopFrontier
10h 03mBOS-MDW
$100
8/21mié.
1 stopFrontier
10h 26mMDW-BOS
8/28mié.
1 stopFrontier
13h 39mBOS-MDW
$101
8/16vie.
1 stopFrontier
9h 56mMDW-BOS
8/20mar.
1 stopFrontier
7h 37mBOS-MDW
$103
8/14mié.
1 stopFrontier
10h 26mMDW-BOS
8/17sáb.
1 stopFrontier
7h 25mBOS-MDW
$104
8/22jue.
1 stopFrontier
10h 26mMDW-BOS
8/26lun.
1 stopFrontier
7h 53mBOS-MDW
$106
8/15jue.
1 stopDelta
5h 13mMDW-PWM
8/20mar.
1 stopDelta
4h 01mPWM-MDW
$196
8/15jue.
1 stopDelta
5h 13mMDW-PWM
8/20mar.
2 stopsDelta
10h 20mPWM-MDW
$201
6/28vie.
1 stop
10h 15mMDW-BOS
7/5vie.
1 stop
5h 57mBOS-MDW
$427
6/28vie.
1 stop
10h 15mMDW-BOS
7/1lun.
2 stops
12h 52mBOS-MDW
$428
6/26mié.
1 stopPorter Airlines
6h 07mMDW-BOS
6/30dom.
1 stopPorter Airlines
15h 02mBOS-MDW
$507

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Recent one-way flight deals

8/24sáb.
1 stopFrontier
10h 26mMDW-BOS
$54
8/14mié.
1 stopFrontier
10h 26mMDW-BOS
$56
6/20jue.
nonstopSouthwest
2h 15mMDW-BOS
$114
7/1lun.
1 stopAllegiant Air
10h 15mMDW-BOS
$121
8/10sáb.
2 stopsDelta
11h 36mMDW-PWM
$129
10/11vie.
1 stopAllegiant Air
12h 12mMDW-BOS
$129
6/20jue.
1 stopSouthwest
5h 05mMDW-BOS
$140
7/1lun.
2 stops
16h 17mMDW-BOS
$150
7/19vie.
2 stops
16h 27mMDW-BOS
$155
7/9mar.
1 stopDelta
5h 25mMDW-BOS
$158

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Last minute flights from Midway to Maine

Last minute flight, train and bus deals

6/18mar.
multi-stopFrontier
7h 42mMDW-BOS
6/26mié.
multi-stopFrontier
6h 43mBOS-MDW
$149
6/18mar.
multi-stopFrontier
7h 42mMDW-BOS
6/27jue.
multi-stopFrontier
8h 34mBOS-MDW
$150
6/16dom.
multi-stopDelta
5h 11mMDW-BOS
6/20jue.
multi-stopDelta
4h 28mBOS-MDW
$334
6/17lun.
multi-stopDelta
5h 11mMDW-BOS
6/19mié.
multi-stopDelta
4h 28mBOS-MDW
$336
6/18mar.
multi-stopPorter Airlines
9h 15mMDW-BOS
7/3mié.
multi-stopPorter Airlines
5h 57mBOS-MDW
$673
6/18mar.
multi-stopPorter Airlines
9h 15mMDW-BOS
7/5vie.
multi-stopPorter Airlines
12h 52mBOS-MDW
$679
6/16dom.
multi-stop
36h 45mMDW-BOS
6/26mié.
multi-stop
5h 57mBOS-MDW
$689
6/18mar.
multi-stop
6h 07mMDW-BOS
6/23dom.
multi-stop
22h 22mBOS-MDW
$699
6/16dom.
multi-stopAir Transat
21h 20mMDW-BOS
6/23dom.
multi-stopAir Transat
10h 57mBOS-MDW
$1,190
6/17lun.
multi-stopAir Transat
9h 15mMDW-BOS
6/20jue.
multi-stopAir Transat
5h 57mBOS-MDW
$1,283

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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: