$96 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 7/18. 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, 0 bags

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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Cheap Flights from Midway to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$181
Albany
Albany1 stop$318
Boston
Bostonnonstop$181
Albany
Albany1 stop$318

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, Jul 3 - Wed, Sep 30
Southwest Logo
7:35 pm - 10:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
1:20 pm - 7:05 pm
BOS
-
MDW
6h 45m
2 stops
$181Southwest
Mon, Jun 29 - Sat, Jul 4
Southwest Logo
7:35 pm - 10:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:40 pm - 7:30 pm
BOS
-
MDW
2h 50mnonstop
$182Southwest
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
8:40 am - 4:00 pm
MDW
-
BOS
6h 20m
2 stops
Southwest Logo
7:05 am - 8:40 am
BOS
-
MDW
2h 35mnonstop
$183Southwest
Sat, Jul 4 - Tue, Jul 7
Southwest Logo
11:10 am - 8:35 pm
MDW
-
BOS
8h 25m
2 stops
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$185Southwest
Sat, Aug 8 - Wed, Aug 12
Southwest Logo
6:35 am - 5:30 pm
MDW
-
BOS
9h 55m
2 stops
Southwest Logo
7:15 pm - 8:50 pm
BOS
-
MDW
2h 35mnonstop
$186Southwest
Mon, Jun 29 - Fri, Jul 3
Southwest Logo
7:35 pm - 10:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:45 pm - 8:35 pm
BOS
-
MDW
2h 50mnonstop
$187Southwest
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
4:55 pm - 8:45 pm
BOS
-
MDW
4h 50m
1 stop
$188Southwest
Sat, Jul 4 - Thu, Jul 23
Southwest Logo
8:55 am - 5:00 pm
MDW
-
BOS
7h 05m
1 stop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$189Southwest
Thu, Sep 10 - Sun, Sep 13
Delta Logo
5:59 pm - 11:06 pm
MDW
-
ALB
4h 07m
1 stop
Delta Logo
6:00 am - 8:42 am
ALB
-
MDW
3h 42m
1 stop
$321Delta
Fri, Jul 31 - Tue, Aug 4
Delta Logo
5:10 pm - 11:54 pm
MDW
-
BDL
5h 44m
1 stop
Delta Logo
5:30 am - 9:17 am
BDL
-
MDW
4h 47m
1 stop
$337Delta
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Massachusetts departing in July.

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 5 days was to Boston, at $196 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 5 days was $196.

What is the cheapest time of day to fly to Massachusetts?

The average price for all round-trip flights from Chicago Midway Airport to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $223 on average. Morning departures are around 17% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $261.

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 2 stops layover the cheapest option at $174 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 November, when tickets cost $89 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $187 and $177 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 Thursday 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 5 weeks before departure, which saves you about 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly and prices are also 24% lower on average.
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.

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 $128 one-way - $231 round-trip

Reviews of the top airline 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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)