$59 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 12/3. 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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Flight Deals

Cheap Flights from Midway to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$117
Albany
Albanynonstop$231
Boston
Bostonnonstop$117
Albany
Albanynonstop$231

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

Thu, Nov 13 - Sat, Nov 15
Frontier Logo
10:12 am - 8:28 amMDW-BOS
21h 16m1 stop
Frontier Logo
11:43 am - 9:35 pmBOS-MDW
10h 52m1 stop
$119Frontier
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Thu, Nov 13 - Sat, Nov 15
Frontier Logo
10:12 am - 8:28 amMDW-BOS
21h 16m1 stop
Frontier Logo
11:43 am - 9:35 pmBOS-MDW
10h 52m1 stop
$121Frontier
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Thu, Nov 27 - Wed, Dec 3
Southwest Logo
1:40 pm - 4:55 pmMDW-BOS
2h 15mnonstop
Southwest Logo
1:35 pm - 3:20 pmBOS-MDW
2h 45mnonstop
$122Southwest
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Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
Frontier Logo
11:28 am - 9:52 amBOS-MDW
23h 24m1 stop
$123Frontier
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Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
Frontier Logo
11:28 am - 9:52 amBOS-MDW
23h 24m1 stop
$124Frontier
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Thu, Dec 4 - Sun, Dec 7
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
6:50 pm - 11:30 pmBOS-MDW
5h 40m1 stop
$127Southwest
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
6:05 am - 8:49 pmMDW-BOS
13h 44m1 stop
Multiple Airlines Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
$148Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
3:52 pm - 10:01 amMDW-BOS
17h 09m1 stop
Multiple Airlines Logo
11:28 am - 10:12 pmBOS-MDW
11h 44m1 stop
$153Multiple Airlines
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Sat, Jan 31 - Sun, Feb 1
Delta Logo
11:45 am - 8:11 pmMDW-BDL
7h 26m1 stop
Delta Logo
5:00 pm - 10:26 pmBDL-MDW
6h 26m1 stop
$177Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:25 pm - 11:47 pmMDW-BDL
5h 22m1 stop
Delta Logo
5:40 am - 8:50 amBDL-MDW
4h 10m1 stop
$245Delta
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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.

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 $117 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 $117.

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 $173 (return) on average. On the other hand, the most expensive months are September and February, when the average cost of round-trip tickets is $330 and $323 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 Wednesday, 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

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Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 4% 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 $223 on average. Morning departures are around 16% 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 $273.

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.
8.0
SouthwestOverall score based on 4243 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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