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$59+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$123
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$172 or less

Good one-way deal

$65 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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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. 5% potential increase in price ($12 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 November 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 November 26, 2025.

This Southwest deal was found by Cheapflights users on 11/24. 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.
Thu 12/256:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 11/24$123
This Southwest deal was found by Cheapflights users on 11/24. 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.
Fri 12/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/75:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/24$127
This Southwest deal was found by Cheapflights users on 11/23. 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.
Fri 12/122:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Sat 1/35:20 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/23$129
This Southwest deal was found by Cheapflights users on 11/23. 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.
Thu 12/111:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 1/115:20 amBOS - MDW
Nonstop2h 50mSouthwest
Deal found 11/23$132
This Southwest deal was found by Cheapflights users on 11/24. 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.
Thu 12/256:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sat 1/37:05 pmBOS - MDW
1 stop5h 50mSouthwest
Deal found 11/24$134
This Southwest deal was found by Cheapflights users on 11/24. 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.
Thu 12/189:35 amMDW - BOS
Nonstop2h 15mSouthwest
Thu 12/183:25 pmBOS - MDW
1 stop6h 15mSouthwest
Deal found 11/24$141
This Southwest deal was found by Cheapflights users on 11/24. 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.
Fri 12/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Wed 12/109:05 amBOS - MDW
2 stops6h 00mSouthwest
Deal found 11/24$142
This Southwest deal was found by Cheapflights users on 11/24. 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.
Tue 12/212:25 pmMDW - BOS
1 stop8h 50mSouthwest
Fri 12/55:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/24$143
This Southwest deal was found by Cheapflights users on 11/24. 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.
Thu 12/412:55 pmMDW - BOS
1 stop5h 25mSouthwest
Sun 12/710:40 amBOS - MDW
1 stop11h 10mSouthwest
Deal found 11/24$147
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMDW - BDL
1 stop28h 30mFrontier
Mon 12/152:07 pmBDL - MDW
1 stop8h 51mFrontier
Deal found 11/25$216
This Southwest deal was found by Cheapflights users on 11/24. 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 12/171:25 pmMDW - ALB
Nonstop1h 50mSouthwest
Thu 1/15:10 amALB - MDW
Nonstop2h 20mSouthwest
Deal found 11/24$250
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmMDW - BDL
1 stop20h 14mMultiple Airlines
Sat 12/138:05 amBDL - MDW
2 stops14h 17mMultiple Airlines
Deal found 11/26$261

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 November 26, 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

Fri 12/12

2:25 pm-5:40 pm

Nonstop2h 15m

Boston Logan Intl

Sun 12/14

5:15 am-7:00 am

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

5:30 am-7:20 am

Nonstop2h 50m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/13

1:15 pm-7:35 pm

1 stop5h 20m

Boston Logan Intl

Mon 12/15

5:30 am-7:15 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/18

9:35 am-12:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 12/18

3:25 pm-8:40 pm

1 stop6h 15m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/26

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Sat 1/3

7:05 pm-11:55 pm

1 stop5h 50m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/25

12:55 pm-7:10 pm

1 stop5h 15m

Boston Logan Intl

Sat 1/3

7:05 pm-11:55 pm

1 stop5h 50m

$159

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/24

11:25 am-5:20 pm

1 stop4h 55m

Boston Logan Intl

Wed 12/31

5:35 pm-9:05 pm

1 stop4h 30m

$172

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/24

11:25 am-5:20 pm

1 stop4h 55m

Boston Logan Intl

Mon 1/5

6:55 pm-8:45 pm

Nonstop2h 50m

$174

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 1/16

6:30 pm-11:40 pm

1 stop4h 10m

Hartford Bradley Intl

Mon 1/19

5:00 pm-10:22 pm

1 stop6h 22m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 1/20

6:35 pm-11:40 pm

1 stop4h 05m

Hartford Bradley Intl

Fri 1/23

2:49 pm-10:22 pm

1 stop8h 33m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 54 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 $99). 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 November 26, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 70% on flights from Chicago Midway Airport to Massachusetts by exploring options for tickets in the evening.

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 November 25, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Massachusetts flight should consider departing on Friday evenings 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.

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 November 26, 2025.
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
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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 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 $226, our data indicates the cheapest price to be $58. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $123.

  • 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 $99). 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 LaGuardia flights
Midway to Tampa 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$136Average$291FlexibilityNo cancel feeOn-time63%

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