$42 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 8/9. 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
1 adult, Economy

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
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$125
Bangor
Bangor2 stops$274
Boston
Bostonnonstop$84
Portland
Portland1 stop$125
Bangor
Bangor2 stops$274
Boston
Bostonnonstop$84

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Maine

Sat, Aug 9 - Thu, Aug 14
Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$84Southwest
Find Deal
Wed, Sep 3 - Sat, Sep 6
Southwest Logo
9:00 am - 4:10 pmMDW-BOS
6h 10m1 stop
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
$89Southwest
Find Deal
Sat, Aug 9 - Thu, Aug 14
Southwest Logo
2:50 pm - 8:55 pmMDW-BOS
5h 05m1 stop
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$94Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:30 am - 7:05 amBOS-MDW
2h 35mnonstop
$95Southwest
Find Deal
Wed, Aug 27 - Thu, Aug 28
Southwest Logo
10:05 am - 5:05 pmMDW-BOS
6h 00m2 stops
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$99Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
$101Southwest
Find Deal
Sat, Aug 16 - Tue, Aug 19
Southwest Logo
9:35 am - 3:40 pmMDW-BOS
5h 05m1 stop
Southwest Logo
5:40 am - 11:45 amBOS-MDW
7h 05m1 stop
$104Southwest
Find Deal
Wed, Sep 3 - Fri, Sep 12
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m2 stops
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
$105Southwest
Find Deal
Sat, Aug 16 - Wed, Aug 20
Delta Logo
6:17 pm - 11:21 pmMDW-BOS
4h 04m1 stop
Delta Logo
5:35 am - 11:48 amBOS-MDW
7h 13m1 stop
$137Delta
Find Deal
Tue, Aug 19 - Wed, Aug 20
Delta Logo
6:17 pm - 11:53 pmMDW-BOS
4h 36m1 stop
Delta Logo
1:08 pm - 6:37 pmBOS-MDW
6h 29m1 stop
$157Delta
Find Deal
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 $195 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 $195.

Can I save money by flying with a layover from Chicago Midway Airport to Maine?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $289, prices are generally cheapest when you fly direct.

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 Monday. On your return trip to Chicago Midway Airport, you should consider flying back on a Thursday, and avoid Saturdays for better deals.

Find deals

Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$42
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 22% increase in price.
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 $372 on average. Morning departures are around 14% 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 $479.

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 $68 one-way - $137 round-trip

Reviews of the 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 4250 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.