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$67+ Cheap flights from Massachusetts to Midway (MDW)

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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Massachusetts to Midway

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

Round-trip from

$127
(Southwest)

One-way from

$67
(Southwest)

Popular in

March

Cheapest in

January

Average price

$199

Good round-trip deal

$192 or less

Good one-way deal

$168 or less
From Massachusetts to Chicago Midway
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One-way flight from Massachusetts to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 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 Massachusetts to Chicago Midway.
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Price to beat on a one-way flight from Massachusetts to Chicago Midway.
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Find flight deals from Massachusetts to Midway

Cheapest flights from Massachusetts to Midway
Explore the most affordable flight options available from Massachusetts to Midway. 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 9/12. 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.
Tue 10/285:15 amBOS - MDW
Nonstop2h 40mSouthwest
Tue 11/42:10 pmMDW - BOS
2 stops7h 05mSouthwest
Deal found 9/12$124
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 10/255:05 amBOS - MDW
2 stops8h 15mSouthwest
Mon 10/2711:25 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/12$125
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Wed 10/2910:10 amMDW - BOS
2 stops8h 10mSouthwest
Deal found 9/12$126
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.
Thu 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
Mon 10/65:50 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/14$127
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 10/45:20 amBOS - MDW
Nonstop2h 40mSouthwest
Tue 10/75:35 amMDW - BOS
1 stop4h 45mSouthwest
Deal found 9/12$129
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 12/121:45 pmBOS - MDW
Nonstop2h 45mSouthwest
Sun 12/146:20 amMDW - BOS
1 stop5h 45mSouthwest
Deal found 9/12$131
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.
Thu 10/239:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/269:20 pmMDW - BOS
1 stop9h 55mSouthwest
Deal found 9/13$133
This Southwest deal was found by Cheapflights users on 9/12. 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.
Thu 10/169:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sat 10/186:30 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/12$135
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Mon 10/274:35 pmMDW - BOS
2 stops6h 20mSouthwest
Deal found 9/12$136
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.
Sat 9/205:50 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 9/224:45 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 9/13$137
This Frontier deal was found by Cheapflights users on 9/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2112:18 pmBDL - MDW
1 stop12h 02mFrontier
Mon 9/228:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 9/12$186
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 10/255:30 amBDL - MDW
1 stop7h 10mSouthwest
Mon 10/279:30 amMDW - BDL
Nonstop2h 05mSouthwest
Deal found 9/12$187

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Midway 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 Massachusetts to Chicago Midway Airport that are best for you.

Fly from

Massachusetts

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/3

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Fri 12/5

6:20 am-11:45 am

1 stop4h 25m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Mon 10/6

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/4

2:35 pm-4:15 pm

Nonstop2h 40m

Chicago Midway

Tue 10/7

5:35 am-12:50 pm

1 stop6h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/13

1:45 pm-3:30 pm

Nonstop2h 45m

Chicago Midway

Sun 11/16

5:00 am-12:50 pm

1 stop6h 50m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

10:05 am-2:10 pm

1 stop5h 05m

Chicago Midway

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

$131

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/15

9:20 am-4:20 pm

1 stop8h 00m

Chicago Midway

Mon 11/17

11:25 am-9:40 pm

1 stop9h 15m

$131

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Sun 11/2

5:45 am-5:10 pm

1 stop10h 25m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/25

8:35 am-10:10 am

Nonstop2h 35m

Chicago Midway

Sun 9/28

5:55 am-9:10 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Sun 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Sun 12/7

9:35 am-12:50 pm

Nonstop2h 15m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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

Have a flexible travel schedule? Discover the best time to fly to Midway from Massachusetts 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 Massachusetts to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $160). Flying from Massachusetts to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MA to MDW?

Find hourly flight availability from Massachusetts to Midway. 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.

When flying from Massachusetts to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Midway. 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 Massachusetts to Chicago Midway Airport?

    For as low as $126, Southwest can have you in Chicago Midway Airport from Massachusetts in 4h 30m. Massachusetts and Chicago Midway Airport are separated by a distance of 857 mi. This flight may include one or multiple stops.

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

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

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

    While on average a flight from Massachusetts to Chicago Midway Airport is generally $278, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $117 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Midway 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 Massachusetts to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $160). Flying from Massachusetts to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Massachusetts to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Reagan-National to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
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Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
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Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Jose to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Love Field to Midway flights
Denver to Midway flights
Seattle to Midway flights
Providence to O'Hare Intl flights
Reagan-National to Midway flights

Top 4 airlines flying from Massachusetts to Midway

Discover the top 4 airlines that operate flights from Massachusetts to Midway. 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
United AirlinesCheapest$97Average$177FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$103FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$121Average$262FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$346FlexibilityNo cancel feeOn-timeN/A

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