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$65+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$65
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$244

Good round-trip deal

$187 or less

Good one-way deal

$118 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 ($13 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 October 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 October 16, 2025.

This Southwest deal was found by Cheapflights users on 10/16. 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 11/69:35 amMDW - BOS
1 stop5h 10mSouthwest
Sun 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/16$127
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 12/47:47 pmMDW - BOS
1 stop13h 35mFrontier
Sun 12/711:28 amBOS - MDW
1 stop7h 36mFrontier
Deal found 10/15$128
This Southwest deal was found by Cheapflights users on 10/15. 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 10/2210:10 amMDW - BOS
2 stops8h 10mSouthwest
Sat 10/2510:30 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 10/15$132
This Southwest deal was found by Cheapflights users on 10/16. 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 11/13:50 pmMDW - BOS
1 stop4h 45mSouthwest
Wed 11/55:45 amBOS - MDW
1 stop5h 25mSouthwest
Deal found 10/16$137
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/41:56 pmMDW - BOS
2 stops33h 03mMultiple Airlines
Sat 11/811:43 amBOS - MDW
1 stop7h 56mMultiple Airlines
Deal found 10/15$141
This Southwest deal was found by Cheapflights users on 10/15. 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 11/71:50 pmMDW - BOS
1 stop8h 50mSouthwest
Sun 11/96:50 amBOS - MDW
1 stop9h 50mSouthwest
Deal found 10/15$148
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 10/319:32 amMDW - BOS
1 stop21h 56mMultiple Airlines
Tue 11/46:16 amBOS - MDW
2 stops31h 25mMultiple Airlines
Deal found 10/15$151
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Mon 12/228:15 amMDW - BOS
1 stop24h 29mFrontier
Tue 12/3010:39 amBOS - MDW
1 stop12h 33mFrontier
Deal found 10/16$161
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/122:06 pmMDW - BOS
1 stop17h 54mFrontier
Sat 11/1511:43 amBOS - MDW
1 stop7h 56mFrontier
Deal found 10/15$164
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/122:06 pmMDW - BOS
1 stop17h 54mMultiple Airlines
Sat 11/159:23 amBOS - MDW
2 stops10h 16mMultiple Airlines
Deal found 10/15$166
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:49 amMDW - BDL
1 stop22h 55mFrontier
Mon 10/274:01 pmBDL - MDW
1 stop8h 45mFrontier
Deal found 10/14$179
This Booking.com deal was found by Cheapflights users on 10/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:12 amMDW - BDL
1 stop25h 29mFrontier
Sun 11/161:36 pmBDL - MDW
1 stop19h 56mFrontier
Deal found 10/13$180

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 October 16, 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

Thu 10/23

6:05 am-9:20 am

Nonstop2h 15m

Boston Logan Intl

Thu 10/30

5:00 am-9:05 am

1 stop5h 05m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/1

10:00 am-1:15 pm

Nonstop2h 15m

Boston Logan Intl

Wed 11/5

5:45 am-10:10 am

1 stop5h 25m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/31

4:55 pm-8:10 pm

Nonstop2h 15m

Boston Logan Intl

Sat 11/1

3:25 pm-9:00 pm

1 stop6h 35m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/1

10:00 am-1:15 pm

Nonstop2h 15m

Boston Logan Intl

Tue 11/4

8:30 am-4:00 pm

1 stop8h 30m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/6

5:15 pm-10:55 pm

1 stop4h 40m

Boston Logan Intl

Sun 11/9

5:15 am-7:00 am

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/7

1:50 pm-11:40 pm

1 stop8h 50m

Boston Logan Intl

Sun 11/9

6:50 am-3:40 pm

1 stop9h 50m

$148

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Sun 12/7

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 10/30

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Sat 11/1

4:45 pm-6:30 pm

Nonstop2h 45m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

2:25 pm-5:40 pm

Nonstop2h 15m

Boston Logan Intl

Sun 11/16

5:15 am-7:00 am

Nonstop2h 45m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 11/4

9:35 am-4:09 pm

1 stop5h 34m

Hartford Bradley Intl

Tue 11/11

6:05 am-1:07 pm

1 stop8h 02m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 56 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 $104). 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 October 16, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 69% 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 October 12, 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. Wednesday at noon 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 October 16, 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
4,241 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

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 $228, our data indicates the cheapest price to be $58. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $117.

  • 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 $104). 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 Los Angeles flights

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$137Average$289FlexibilityNo cancel feeOn-time63%

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