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$64+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap 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 December 26, 2025.

This Southwest deal was found by Cheapflights users on 12/24. 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.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Wed 1/72:00 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 12/24$188
This Southwest deal was found by Cheapflights users on 12/26. 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.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Mon 1/56:45 amMDW - BOS
1 stop10h 30mSouthwest
Deal found 12/26$213
This Southwest deal was found by Cheapflights users on 12/26. 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.
Mon 12/296:50 pmBOS - MDW
Nonstop2h 55mSouthwest
Fri 1/29:40 pmMDW - BOS
1 stop9h 35mSouthwest
Deal found 12/26$278
This Southwest deal was found by Cheapflights users on 12/25. 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 12/307:00 amBOS - MDW
1 stop9h 20mSouthwest
Tue 1/61:50 pmMDW - BOS
1 stop6h 35mSouthwest
Deal found 12/25$287
This Southwest deal was found by Cheapflights users on 12/25. 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 12/307:00 amBOS - MDW
1 stop9h 20mSouthwest
Fri 1/29:40 pmMDW - BOS
1 stop9h 35mSouthwest
Deal found 12/25$303
This Delta deal was found by Cheapflights users on 12/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:47 pmBDL - MDW
1 stop6h 35mDelta
Fri 1/26:08 pmMDW - BDL
1 stop4h 06mDelta
Deal found 12/24$447
This Southwest deal was found by Cheapflights users on 12/24. 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 12/278:05 pmBDL - MDW
Nonstop2h 30mSouthwest
Thu 1/16:35 amMDW - BDL
1 stop7h 20mSouthwest
Deal found 12/24$529
This Southwest deal was found by Cheapflights users on 12/23. 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.
Sun 12/285:10 amALB - MDW
Nonstop2h 20mSouthwest
Wed 12/311:25 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 12/23$559
This Delta deal was found by Cheapflights users on 12/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:36 pmALB - MDW
1 stop5h 50mDelta
Thu 1/16:00 amMDW - ALB
1 stop6h 18mDelta
Deal found 12/24$585
This Delta deal was found by Cheapflights users on 12/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:48 pmBDL - MDW
1 stop5h 38mDelta
Thu 1/16:08 pmMDW - BDL
1 stop4h 06mDelta
Deal found 12/24$637
This Southwest deal was found by Cheapflights users on 12/26. 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 12/275:10 amALB - MDW
Nonstop2h 20mSouthwest
Fri 1/27:45 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 12/26$673
This Kiwi.com deal was found by Cheapflights users on 12/24. 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.
Wed 12/3110:03 amBDL - MDW
2 stops13h 09mMultiple Airlines
Fri 1/23:10 pmMDW - BDL
1 stop22h 39mMultiple Airlines
Deal found 12/24$677

Find flight deals from Massachusetts to Midway

Keep the following information in mind while searching for Massachusetts to Midway flight deals. Data was last updated December 26, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$333 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Chicago Midway
Search Deals
One-way flight from Massachusetts to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago Midway.
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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 December 26, 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

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Tue 1/27

1:50 pm-9:25 pm

1 stop6h 35m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 1/12

1:50 pm-9:25 pm

1 stop6h 35m

$152

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 1/30

5:35 pm-8:50 pm

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 1/30

5:35 pm-8:50 pm

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/11

12:30 pm-10:10 pm

1 stop8h 40m

$158

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 2/26

2:27 pm-10:29 pm

1 stop9h 02m

Chicago Midway

Mon 3/2

9:22 pm-9:23 am

1 stop11h 01m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/1

7:20 am-11:25 am

1 stop5h 05m

Chicago Midway

Mon 1/5

6:45 am-6:15 pm

1 stop10h 30m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/5

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Mon 2/9

6:35 pm-9:50 pm

Nonstop2h 15m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/10

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/11

12:30 pm-10:10 pm

1 stop8h 40m

$163

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/25

4:55 pm-11:20 pm

1 stop5h 25m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 $176). 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 December 26, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 50% 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 December 20, 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. Tuesday evenings 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 $147, Southwest can have you in Chicago Midway Airport from Massachusetts in 2h 50m. 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 $348, our data shows the cheapest flight currently is $73. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $132 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 $176). 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
Lansing
Merrillville
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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$270FlexibilityNo cancel feeOn-time63%
DeltaCheapest$207Average$316FlexibilityNo cancel feeOn-timeN/A

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