HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

September

Average price

$250

Good round-trip deal

$232 or less

Good one-way deal

$93 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. 5% potential increase in price ($12 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 November 2025
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

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 14, 2025.

This Southwest deal was found by Cheapflights users on 11/12. 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 12/127:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/12$117
This Southwest deal was found by Cheapflights users on 11/12. 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 12/116:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sat 12/135:20 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/12$122
This Southwest deal was found by Cheapflights users on 11/14. 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 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 11/14$123
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/318:15 amMDW - BOS
1 stop15h 59mFrontier
Thu 1/16:00 amBOS - MDW
1 stop12h 38mFrontier
Deal found 11/12$125
This Frontier deal was found by Cheapflights users on 11/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmMDW - BOS
1 stop17h 47mFrontier
Sun 12/1411:28 amBOS - MDW
1 stop7h 44mFrontier
Deal found 11/14$126
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:50 pmMDW - BOS
Nonstop2h 15mSouthwest
Mon 12/85:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/13$127
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - BOS
1 stop13h 59mFrontier
Sun 12/1411:28 amBOS - MDW
1 stop23h 24mFrontier
Deal found 11/13$130
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:40 amMDW - BOS
1 stop5h 15mSouthwest
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/13$132
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/298:15 amMDW - BOS
1 stop16h 04mFrontier
Thu 1/16:00 amBOS - MDW
1 stop17h 12mFrontier
Deal found 11/12$133
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Thu 12/186:50 pmBOS - MDW
1 stop5h 40mSouthwest
Deal found 11/13$134
This Southwest deal was found by Cheapflights users on 11/12. 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 11/195:35 amMDW - BOS
1 stop6h 55mSouthwest
Thu 11/205:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/12$137
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/206:12 amMDW - BDL
1 stop27h 58mFrontier
Sat 1/1012:38 pmBDL - MDW
2 stops27h 40mFrontier
Deal found 11/12$175

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 14, 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

7:15 pm-10:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 12/14

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/11

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/14

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

7:50 pm-11:05 pm

Nonstop2h 15m

Boston Logan Intl

Thu 12/4

5:30 am-7:15 am

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/6

9:50 am-1:10 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

10:40 am-8:50 pm

1 stop11h 10m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/11

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Thu 12/18

6:50 pm-11:30 pm

1 stop5h 40m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/19

6:20 am-11:45 am

1 stop4h 25m

Boston Logan Intl

Sat 11/22

5:05 am-9:30 am

1 stop5h 25m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 2/6

6:35 pm-9:50 pm

Nonstop2h 15m

Boston Logan Intl

Wed 2/11

1:20 pm-6:35 pm

2 stops6h 15m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 12/30

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Fri 1/2

5:15 am-7:00 am

Nonstop2h 45m

$161

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 12/22

7:50 pm-11:05 pm

Nonstop2h 15m

Boston Logan Intl

Tue 12/30

5:15 am-7:00 am

Nonstop2h 45m

$164

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 1/29

6:00 am-1:42 pm

1 stop6h 42m

Hartford Bradley Intl

Sun 2/1

5:30 am-8:54 am

1 stop4h 24m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 56 results
1
2
3
...
6

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 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 68% 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 2, 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 14, 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
4,244 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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 cheapest airlines to fly from Chicago Midway Airport to Massachusetts one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $61. Southwest flights start at $64 while deals on Delta start at $126 one-way.

  • 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 $255, our data indicates the cheapest price to be $58. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $122.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Orlando flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Denver flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Tampa flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Seattle flights
Midway to LaGuardia flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Boston flights
O'Hare Intl to Honolulu flights
Midway to Las Vegas flights
Midway to Atlanta flights
O'Hare Intl to Santa Ana flights
Midway to Orlando flights
O'Hare Intl to Ontario flights
O'Hare Intl to Baltimore flights
Midway to Miami flights
O'Hare Intl to San Diego flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to New Orleans flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Reagan-National flights
Midway to Los Angeles flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Austin flights
O'Hare Intl to Sarasota flights
O'Hare Intl to West Palm Beach flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Nashville flights
O'Hare Intl to Love Field flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Palm Springs flights
Midway to Fort Lauderdale flights
O'Hare Intl to Hobby flights
O'Hare Intl to Key West flights
Midway to Hobby flights
Midway to Denver flights
Midway to Newark 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 November 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$137Average$294FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.