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$59+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
dic. 4 — dic. 111
jue. 12/4
jue. 12/11
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 noviembre 4, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

September

Average price

$248

Good round-trip deal

$238 or less

Good one-way deal

$180 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 4, 2025.

This Southwest deal was found by Cheapflights users on 11/4. 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.
jue. 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
dom. 12/77:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 11/4$117
This Southwest deal was found by Cheapflights users on 11/3. 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.
lun. 12/85:30 amBOS - MDW
Nonstop2h 45mSouthwest
lun. 12/227:50 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 11/3$124
This Southwest deal was found by Cheapflights users on 11/2. 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.
lun. 11/101:45 pmBOS - MDW
Nonstop2h 45mSouthwest
mié. 11/126:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 11/2$127
This Frontier deal was found by Cheapflights users on 11/3. 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.
jue. 12/1111:28 amBOS - MDW
1 stop11h 44mFrontier
dom. 1/182:12 pmMDW - BOS
1 stop9h 46mFrontier
Deal found 11/3$128
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/1111:28 amBOS - MDW
1 stop11h 44mFrontier
sáb. 1/106:00 amMDW - BOS
1 stop18h 04mFrontier
Deal found 11/3$129
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/411:28 amBOS - MDW
1 stop7h 40mFrontier
dom. 12/76:15 amMDW - BOS
1 stop27h 07mFrontier
Deal found 11/4$130
This Southwest deal was found by Cheapflights users on 11/4. 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.
mié. 12/39:05 amBOS - MDW
2 stops6h 00mSouthwest
dom. 12/77:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 11/4$132
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/511:19 amBOS - MDW
1 stop9h 23mMultiple Airlines
lun. 12/83:10 pmMDW - BOS
1 stop17h 51mMultiple Airlines
Deal found 11/4$135
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/121:30 pmBDL - MDW
2 stops10h 09mMultiple Airlines
dom. 12/146:37 pmMDW - BDL
1 stop17h 35mMultiple Airlines
Deal found 11/2$217
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/255:42 pmBDL - MDW
1 stop24h 15mFrontier
jue. 12/47:23 pmMDW - BDL
1 stop14h 45mFrontier
Deal found 11/2$219
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2010:54 amBDL - MDW
2 stops12h 23mFrontier
mié. 11/265:30 pmMDW - BDL
1 stop25h 02mFrontier
Deal found 11/2$220
This Southwest deal was found by Cheapflights users on 11/2. 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.
mié. 11/268:00 pmBDL - MDW
Nonstop2h 30mSouthwest
jue. 11/272:00 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/2$225

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 noviembre 4, 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

jue. 12/4

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

dom. 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$117

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 12/5

6:00 pm-10:35 pm

1 stop5h 35m

Chicago Midway

dom. 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

sáb. 2/14

5:55 pm-10:30 pm

1 stop5h 35m

Chicago Midway

mar. 2/17

10:45 am-4:05 pm

1 stop4h 20m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 11/14

6:55 pm-8:45 pm

Nonstop2h 50m

Chicago Midway

lun. 11/17

11:25 am-5:20 pm

1 stop4h 55m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

lun. 11/17

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

mié. 11/19

5:35 am-1:30 pm

1 stop6h 55m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

sáb. 11/15

5:20 am-7:05 am

Nonstop2h 45m

Chicago Midway

mié. 11/19

5:35 am-1:30 pm

1 stop6h 55m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 12/18

6:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

dom. 12/21

5:30 am-8:45 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 12/12

11:19 am-7:42 pm

1 stop9h 23m

Chicago Midway

dom. 12/14

6:15 am-10:22 am

1 stop27h 07m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 2/20

12:50 pm-7:50 pm

2 stops8h 00m

Chicago Midway

dom. 2/22

5:50 am-11:20 am

1 stop4h 30m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 2/25

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

sáb. 2/28

1:55 pm-10:15 pm

1 stop7h 20m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 59 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, June is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $97). Flying from Massachusetts to Chicago Midway Airport in April is currently the most expensive (average of $175). 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 noviembre 4, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 45% on flights from Massachusetts to Chicago Midway Airport by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Midway. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Massachusetts to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 $117, Southwest can have you in Chicago Midway Airport from Massachusetts in 2h 45m. Massachusetts and Chicago Midway Airport are separated by a distance of 857 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $59. Users have also found prices from $119 and $122 on Frontier and Delta, respectively.

  • 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 $306, our data shows the cheapest flight currently is $58. 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, June is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $97). Flying from Massachusetts to Chicago Midway Airport in April is currently the most expensive (average of $175). 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
Porter
Benton Harbor

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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.
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Top 2 airlines flying from Massachusetts to Midway

Discover the top 2 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 noviembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$274FlexibilityNo cancel feeOn-time63%
DeltaCheapest$207Average$318FlexibilityNo cancel feeOn-timeN/A

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