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$69+ Cheap flights from Midway (MDW) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Okt 15 — Okt 221
Mi 10/15
Mi 10/22
1 adult, Economy
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Cheap flight deals from Midway to Massachusetts

Keep the following information in mind while searching for Midway to Massachusetts flight deals. Data was last updated September 15, 2025.

Round-trip from

$132
(Southwest)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

September

Average price

$207

Good round-trip deal

$99 or less

Good one-way deal

$86 or less
From Chicago Midway to Massachusetts
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One-way flight from Chicago Midway to Massachusetts
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Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Massachusetts.
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Price to beat on a one-way flight from Chicago Midway to Massachusetts.
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Find flight deals from Midway to Massachusetts

Cheapest flights from Midway to Massachusetts
Explore the most affordable flight options available from Midway to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 11/149:30 amMDW - BOS
2 stops7h 45mSouthwest
So 11/165:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/13$132
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 11/76:45 amMDW - BOS
1 stop10h 25mSouthwest
So 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 11/265:30 amMDW - BOS
Nonstop2h 15mSouthwest
Di 12/305:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/14$137
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 11/141:50 pmMDW - BOS
2 stops8h 05mSouthwest
Mo 11/175:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 9/13$138
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 10/183:50 pmMDW - BOS
1 stop4h 45mSouthwest
Sa 10/255:05 amBOS - MDW
2 stops8h 15mSouthwest
Deal found 9/14$142
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 12/139:50 amMDW - BOS
Nonstop2h 20mSouthwest
Mi 12/175:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 9/14$143
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 9/266:21 amMDW - BOS
1 stop24h 50mFrontier
Sa 10/48:56 amBOS - MDW
1 stop28h 48mFrontier
Deal found 9/13$144
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 11/141:50 pmMDW - BOS
2 stops8h 05mSouthwest
Sa 11/155:55 amBOS - MDW
2 stops11h 35mSouthwest
Deal found 9/13$147
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 9/2310:05 amMDW - BOS
2 stops6h 00mSouthwest
Fr 9/268:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 9/14$152
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 11/211:50 pmMDW - BOS
1 stop8h 50mSouthwest
So 11/235:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/13$153
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 12/127:15 pmMDW - BOS
Nonstop2h 15mSouthwest
So 1/45:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/13$157
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 11/69:05 pmMDW - BDL
1 stop10h 00mSouthwest
So 11/93:35 pmBDL - MDW
1 stop8h 35mSouthwest
Deal found 9/13$182

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Massachusetts that are best for you.

Fly from

Midway

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mi 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

Boston Logan Intl

Fr 11/28

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fr 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Mo 12/8

5:30 am-7:15 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mi 11/26

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Di 12/30

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mi 10/22

12:30 pm-5:45 pm

1 stop4h 15m

Boston Logan Intl

Mi 10/29

9:10 am-2:25 pm

1 stop6h 15m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fr 11/14

1:50 pm-10:55 pm

2 stops8h 05m

Boston Logan Intl

Sa 11/15

5:55 am-4:30 pm

2 stops11h 35m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fr 11/14

9:30 am-6:15 pm

2 stops7h 45m

Boston Logan Intl

Di 11/18

8:30 am-4:50 pm

2 stops9h 20m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fr 11/21

1:50 pm-11:40 pm

1 stop8h 50m

Boston Logan Intl

Mo 11/24

5:15 am-7:00 am

Nonstop2h 45m

$153

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sa 12/13

9:45 am-5:05 pm

2 stops6h 20m

Boston Logan Intl

Mi 12/17

9:05 am-2:05 pm

2 stops6h 00m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fr 12/12

9:30 am-6:15 pm

2 stops7h 45m

Boston Logan Intl

So 1/4

5:15 am-7:00 am

Nonstop2h 45m

$172

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Do 11/6

9:05 pm-8:05 am

1 stop10h 00m

Hartford Bradley Intl

So 11/9

3:35 pm-11:10 pm

1 stop8h 35m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Massachusetts

What is the cheapest month to book a flight from Chicago Midway Airport to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $218). Flying from Chicago Midway Airport to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to MA?

Find hourly flight availability from Midway to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Massachusetts as you normally would.

How much does it cost to fly round-trip from Chicago Midway Airport to Massachusetts?

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated September 15, 2025.
See what other customers who have flown with Southwest and United Airlines from Chicago Midway Airport to Massachusetts have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Massachusetts?

    Departing from Chicago Midway Airport to Massachusetts will take you 2h 15m. Chicago Midway Airport and Massachusetts are separated by a distance of 857 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Massachusetts one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $69. Frontier flights start at $79 while deals on Delta start at $126 one-way.

  • What are the most popular routes from Chicago Midway Airport to Massachusetts?

    The most popular route from Chicago Midway Airport to Massachusetts is Chicago Midway - Boston Logan Intl. You may also consider Chicago Midway - Hartford Bradley Intl or Chicago Midway - Albany Intl.

  • What are the cheapest flights from Chicago Midway Airport to Massachusetts?

    Looking for the cheapest flight from Chicago Midway Airport to Massachusetts? While on average our users pay $233, our data indicates the cheapest price to be $45. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $100.

  • Can I find deals for flights from Midway to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Midway to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Massachusetts.

  • Can I find deals for business class flights from Midway to Massachusetts?

    Yes. Cheapflights offers flight deals from Midway to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $218). Flying from Chicago Midway Airport to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Midway to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Orlando flights
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Midway to Hobby flights
O'Hare Intl to Charlotte flights
Midway to San Francisco flights
Midway to Miami flights
O'Hare Intl to Hobby flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Minneapolis flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Love Field flights
Midway to Seattle flights

Top 2 airlines flying from Midway to Massachusetts

Discover the top 2 airlines that operate flights from Midway to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$142Average$290FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$297FlexibilityNo cancel feeOn-time69%

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