$59 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 5/10. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Maine

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maine, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maine, as well as popular online travel agencies
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Flights Deals

Best Maine Flight Deals from Midway

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

Portland
Portland1 stop$223
Bangor
Bangor2 stops$324
Boston
Bostonnonstop$117
Portland
Portland1 stop$223
Bangor
Bangor2 stops$324
Boston
Bostonnonstop$117

Cheap Flights from Midway to Maine

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Maine that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Maine

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Maine.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
7:20 pm - 10:35 pmMDW-BOS
2h 15mnonstop
Southwest Logo
7:40 am - 9:15 amBOS-MDW
2h 35mnonstop
$117Southwest
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Fri, May 30 - Sun, Jun 1
Southwest Logo
2:50 pm - 10:45 pmMDW-BOS
6h 55m1 stop
Southwest Logo
5:15 am - 6:50 amBOS-MDW
2h 35mnonstop
$127Southwest
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Thu, Jun 12 - Mon, Jun 16
Allegiant Air Logo
9:12 am - 12:01 pmMDW-BOS
25h 49m1 stop
Allegiant Air Logo
11:31 am - 7:15 amBOS-MDW
20h 44m1 stop
$206Allegiant Air
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Fri, Jun 13 - Sun, Jun 15
Frontier Logo
1:19 pm - 12:44 amMDW-BOS
10h 25m1 stop
Frontier Logo
8:00 am - 12:24 pmBOS-MDW
29h 24m1 stop
$211Frontier
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Mon, May 12 - Wed, May 14
Allegiant Air Logo
2:53 pm - 9:17 amMDW-BOS
17h 24m1 stop
Allegiant Air Logo
11:31 am - 7:15 amBOS-MDW
20h 44m1 stop
$214Allegiant Air
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Mon, Jun 9 - Thu, Jun 12
Frontier Logo
1:19 pm - 1:05 amMDW-BOS
10h 46m1 stop
Frontier Logo
10:14 am - 10:40 pmBOS-MDW
13h 26m1 stop
$218Frontier
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Thu, May 15 - Sun, May 18
Delta Logo
4:15 pm - 11:59 pmMDW-PWM
6h 44m1 stop
Delta Logo
5:30 am - 11:53 amPWM-MDW
7h 23m1 stop
$223Delta
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Fri, May 30 - Tue, Jun 3
Delta Logo
4:15 pm - 11:59 pmMDW-PWM
6h 44m1 stop
Delta Logo
11:44 am - 5:40 pmPWM-MDW
6h 56m1 stop
$229Delta
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Sat, Jun 7 - Thu, Jun 12
Logo
8:36 pm - 11:47 pmMDW-BOS
26h 11m3 stops
Logo
9:02 am - 7:46 pmBOS-MDW
11h 44m1 stop
$313
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Fri, Jun 13 - Mon, Jun 16
Logo
12:50 pm - 10:30 amMDW-BOS
20h 40m2 stops
Logo
12:01 pm - 11:18 amBOS-MDW
24h 17m1 stop
$320
Find Deal
Mon, Sep 29 - Sun, Oct 5
Useful Info

KAYAK's insights & trends for Midway to Maine flights

Get data-powered insights and trends into flights from Midway to Maine to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Maine flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Maine.

The cheapest ticket to Maine from Chicago Midway Airport found in the last 72 hours was to Portland, at $279 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Portland (PWM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $279.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Maine?

The average price of all round-trip flights from Chicago Midway Airport to Maine clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Maine on a Tuesday and more expensive on a Friday. On your return trip to Chicago Midway Airport, you should consider flying back on a Wednesday, and avoid Saturdays for better deals.

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Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$59
Best time to beat the crowds with an average 45% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 from Chicago Midway Airport to Maine 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 from Chicago Midway Airport to Maine with an airline and back 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 from Chicago Midway Airport to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Maine?

    The cheapest time of day to fly to Maine is generally in the afternoon, when round-trip flights cost $401 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Maine is generally in the evening, which is peak travel time and where the average cost of a ticket is $487.

Top tips for finding cheap flights to Maine

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Boston $58 one-way - $157 round-trip

Top airline flying from Midway to Maine

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maine. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4293 reviews
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Everything you need to know for your flight from Midway to Maine

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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