$69 Find Cheap Flights from Chicago Midway Airport to Massachusetts

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 Massachusetts departing on 10/31. 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 Massachusetts

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

Cheap Flights from Midway to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston2 stops$132
Albany
Albany1 stop$244
Boston
Boston2 stops$132
Albany
Albany1 stop$244

Book Cheap Midway to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Massachusetts 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 Massachusetts

Fri, Nov 14 - Sun, Nov 16
Southwest Logo
1:50 pm - 10:55 pmMDW-BOS
8h 05m2 stops
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$132Southwest
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Fri, Nov 7 - Sun, Nov 9
Southwest Logo
6:45 am - 6:10 pmMDW-BOS
10h 25m1 stop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$133Southwest
Find Deal
Wed, Nov 26 - Fri, Nov 28
Southwest Logo
4:05 pm - 7:20 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$137Southwest
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Fri, Nov 14 - Tue, Nov 18
Southwest Logo
9:30 am - 6:15 pmMDW-BOS
7h 45m2 stops
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$138Southwest
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Fri, Sep 26 - Sat, Oct 4
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$144Frontier
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Wed, Dec 10 - Wed, Dec 17
Frontier Logo
8:00 am - 12:01 amMDW-BOS
15h 01m1 stop
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
$160Frontier
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Sat, Nov 8 - Sat, Nov 15
 Logo
1:37 pm - 11:25 pmMDW-BOS
8h 48m2 stops
 Logo
11:43 am - 9:35 pmBOS-MDW
10h 52m1 stop
Wed, Dec 10 - Tue, Dec 16
 Logo
8:00 am - 12:01 amMDW-BOS
15h 01m1 stop
 Logo
6:15 am - 11:25 pmBOS-MDW
18h 10m2 stops
Tue, Sep 30 - Tue, Oct 7
Delta Logo
12:43 pm - 8:27 pmMDW-BDL
6h 44m1 stop
Delta Logo
5:30 am - 8:40 amBDL-MDW
4h 10m1 stop
$197Delta
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Fri, Dec 12 - Tue, Dec 30
Delta Logo
6:40 pm - 11:35 pmMDW-ALB
3h 55m1 stop
Delta Logo
5:45 am - 8:49 amALB-MDW
4h 04m1 stop
$244Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Massachusetts flights

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

How much is a round-trip flight from Chicago Midway Airport to Massachusetts?

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Chicago Midway Airport found in the last 72 hours was to Boston, at $67 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $67.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $214 on average.

What is the cheapest month to fly from Chicago Midway Airport to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Massachusetts is January, when tickets cost $185 (return) on average. On the other hand, the most expensive months are February and October, when the average cost of round-trip tickets is $323 and $317 respectively.

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

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

If your flying dates are flexible, you should consider flying to Massachusetts on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Massachusetts. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Chicago Midway Airport to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Massachusetts, you should book around 2 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago Midway Airport to Boston

FAQs - booking Massachusetts flights

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

    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 Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Massachusetts 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 Massachusetts?

    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 Massachusetts 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 Massachusetts?

    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 Massachusetts 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 Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $222 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $283.

Top tips for finding cheap flights to Massachusetts

  • 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 $86 one-way - $99 round-trip

Reviews of the top airlines flying from Midway to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Massachusetts. 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 Massachusetts? 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 4242 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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

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