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$66+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap 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 January 20, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 2/76:25 am
MDW
-
BOS
1 stop4h 55m
Southwest
Sun 2/85:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/20$132
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/176:00 am
MDW
-
BOS
1 stop18h 13m
Frontier
Wed 2/256:00 am
BOS
-
MDW
1 stop14h 07m
Frontier
Deal found 1/19$134
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/176:00 am
MDW
-
BOS
1 stop18h 13m
Frontier
Fri 2/276:00 am
BOS
-
MDW
1 stop13h 38m
Frontier
Deal found 1/19$135
This Southwest deal was found by Cheapflights users on 1/18. 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 2/142:10 pm
MDW
-
BOS
1 stop7h 50m
Southwest
Sat 2/215:15 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 1/18$136
This Southwest deal was found by Cheapflights users on 1/19. 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 2/166:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Mon 2/235:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/19$137
This Southwest deal was found by Cheapflights users on 1/19. 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 2/166:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Wed 2/181:20 pm
BOS
-
MDW
2 stops6h 15m
Southwest
Deal found 1/19$138
This Southwest deal was found by Cheapflights users on 1/19. 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 2/179:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Tue 2/245:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/19$142
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/176:00 am
MDW
-
BOS
1 stop18h 13m
Multiple Airlines
Wed 2/185:50 pm
BOS
-
MDW
1 stop21h 06m
Multiple Airlines
Deal found 1/19$143
This Southwest deal was found by Cheapflights users on 1/19. 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 2/62:40 pm
MDW
-
BOS
1 stop6h 30m
Southwest
Sun 2/85:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/19$147
This Southwest deal was found by Cheapflights users on 1/19. 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 1/312:40 pm
MDW
-
BOS
1 stop4h 50m
Southwest
Tue 2/35:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/19$151
This Southwest deal was found by Cheapflights users on 1/18. 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 2/266:05 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Wed 3/45:50 am
BOS
-
MDW
1 stop6h 45m
Southwest
Deal found 1/18$152
This Frontier deal was found by Cheapflights users on 1/20. 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.
Mon 3/29:22 pm
MDW
-
BDL
1 stop11h 01m
Frontier
Thu 3/52:27 pm
BDL
-
MDW
1 stop9h 02m
Frontier
Deal found 1/20$179

Find flight deals from Midway to Massachusetts

Keep the following information in mind while searching for Midway to Massachusetts flight deals. Data was last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$132
(Southwest)

One-way from

$66
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$207

Good round-trip deal

$197 or less

Good one-way deal

$78 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago Midway to Massachusetts
Search Deals
One-way flight from Chicago Midway to Massachusetts
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Massachusetts.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Massachusetts.
Search Deals

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 January 20, 2026.
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

Wed 2/18

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Mon 2/23

5:20 am-7:10 am

Nonstop2h 50m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 2/7

6:25 am-12:20 pm

1 stop4h 55m

Boston Logan Intl

Sun 2/8

5:30 am-7:20 am

Nonstop2h 50m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 2/26

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Tue 3/3

5:30 am-7:20 am

Nonstop2h 50m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/31

2:40 pm-8:30 pm

1 stop4h 50m

Boston Logan Intl

Tue 2/3

5:30 am-7:20 am

Nonstop2h 50m

$151

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/11

1:50 pm-9:25 pm

1 stop6h 35m

Boston Logan Intl

Wed 2/18

5:30 am-7:20 am

Nonstop2h 50m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Sat 2/28

2:50 pm-6:50 pm

1 stop5h 00m

$153

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 2/12

1:25 pm-11:50 pm

1 stop9h 25m

Boston Logan Intl

Thu 2/19

5:20 am-7:10 am

Nonstop2h 50m

$158

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 3/25

6:00 am-12:12 pm

1 stop29h 12m

Hartford Bradley Intl

Mon 3/30

8:08 pm-10:19 pm

2 stops27h 11m

$281

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 2/9

7:00 pm-7:10 pm

2 stops23h 10m

Hartford Bradley Intl

Thu 2/12

2:27 pm-10:34 pm

1 stop9h 07m

$296

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 5/12

12:45 pm-3:40 pm

Nonstop1h 55m

Albany Intl

Mon 5/18

12:40 pm-5:00 pm

1 stop5h 20m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $92). Flying from Chicago Midway Airport to Massachusetts in April is currently the most expensive (average of $188). 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 January 20, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 17% on flights from Chicago Midway Airport to Massachusetts by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Massachusetts. Price data was last updated on January 17, 2026.

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

Weekly flight availability from Chicago Midway Airport to Massachusetts

Explore weekly flight availability from Midway to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 20, 2026.

The most flights from MDW to USMA are scheduled on a Friday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 January 20, 2026.
See what other customers who have flown with Southwest 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
4,267 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 10m. 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 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 $196, our data indicates the cheapest price to be $52. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $97.

  • 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $92). Flying from Chicago Midway Airport to Massachusetts in April is currently the most expensive (average of $188). 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

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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 Seattle flights
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Top airline flying from Midway to Massachusetts

Discover the top airline 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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$136Average$283FlexibilityNo cancel feeOn-time63%

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