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Cheap flights from Midway (MDW) to Massachusetts from $56

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — BOS
Jun 15 — Jun 221
From?
To?
Sat 6/15
Sat 6/22
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Massachusetts?

Find a great deal and save up to 42% by booking at least 51 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago Midway Airport to Massachusetts within the next two weeks, with the cheapest ticket starting at $263.

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

Flights from Chicago Midway Airport to Massachusetts lean towards being more expensive in June. Prices are generally better when you fly from Chicago Midway Airport to Massachusetts in January, with the cheapest ticket starting at $99.

What is the cheapest time of day to fly from MDW to MA?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Massachusetts as you normally would.

Cheap Midway to Massachusetts flights in June & July 2024

Find cheap flight options from Midway to Massachusetts specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Prices were last updated on June 10, 2024.
Check out some of the best flight deals from Chicago to Massachusetts in 2024. More deals are always being added, so be sure to check back regularly.
Wed 7/312:29 pmMDW - BOS
1 stop8h 58mFrontier
Wed 8/1412:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/9$118
Tue 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 7/246:00 amBOS - MDW
1 stop8h 34mFrontier
Deal found 6/8$127
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/199:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/9$128
Mon 6/245:14 pmMDW - BDL
1 stop21h 03mFrontier
Tue 7/912:18 pmBDL - MDW
2 stops10h 07mFrontier
Deal found 6/9$133
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Tue 6/2512:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 6/9$138
Thu 6/208:51 pmMDW - BOS
1 stop10h 25mFrontier
Tue 6/2512:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 6/9$139
Wed 7/312:29 pmMDW - BOS
1 stop8h 58mFrontier
Tue 8/610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/9$140
Wed 7/102:29 pmMDW - BOS
1 stop8h 58mFrontier
Tue 7/1610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/9$141
Wed 7/102:29 pmMDW - BOS
1 stop8h 58mFrontier
Wed 7/176:00 amBOS - MDW
1 stop8h 34mFrontier
Deal found 6/9$143

Midway to Massachusetts 2024 flight deals

Discover exclusive flight deals for travel between Midway and Massachusetts in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 10, 2024.
Check out some of the best flight deals from Chicago to Massachusetts in 2024. More deals are always being added, so be sure to check back regularly.
Sat 8/177:59 pmMDW - BOS
1 stop10h 26mFrontier
Sat 8/2410:10 amBOS - MDW
1 stop10h 03mFrontier
Deal found 6/9$96
Sat 8/177:59 pmMDW - BOS
1 stop10h 26mFrontier
Tue 8/2712:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/9$100
Tue 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Thu 8/1512:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/9$103
Wed 8/287:59 pmMDW - BOS
1 stop10h 26mFrontier
Wed 9/49:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 6/9$104
Thu 8/227:59 pmMDW - BOS
1 stop10h 26mFrontier
Mon 8/2612:20 pmBOS - MDW
1 stop7h 53mFrontier
Deal found 6/9$106
Tue 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Tue 8/2012:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/9$108
Mon 8/197:59 pmMDW - BOS
1 stop10h 26mFrontier
Mon 8/2612:20 pmBOS - MDW
1 stop7h 53mFrontier
Deal found 6/9$114
Wed 7/312:29 pmMDW - BOS
1 stop8h 58mFrontier
Wed 8/1412:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/9$118
Wed 8/72:29 pmMDW - BOS
1 stop8h 58mFrontier
Sat 8/1712:48 pmBOS - MDW
1 stop7h 25mFrontier
Deal found 6/9$122

Midway to Massachusetts flights leaving soon

Find last-minute flight options from Midway to Massachusetts for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 10, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Massachusetts. It's wise to confirm all flight details are correct before booking.
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/199:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/9$128
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Tue 6/2512:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 6/9$138
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Sat 6/2210:12 amBOS - MDW
1 stop24h 19mFrontier
Deal found 6/9$147
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Sat 6/2210:12 amBOS - MDW
1 stop24h 19mFrontier
Deal found 6/9$148
Fri 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Tue 6/1812:42 pmBOS - MDW
1 stop9h 38mFrontier
Deal found 6/9$158
Fri 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Tue 7/1610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/9$167
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Thu 6/2012:22 pmBOS - MDW
1 stop8h 34mFrontier
Deal found 6/9$182
Sun 6/166:56 amMDW - BDL
1 stop11h 52mFrontier
Tue 6/181:17 pmBDL - MDW
2 stops9h 03mFrontier
Deal found 6/9$183
Sun 6/168:53 pmMDW - BOS
1 stop10h 23mFrontier
Tue 6/1812:42 pmBOS - MDW
1 stop9h 38mFrontier
Deal found 6/9$198

One-way flights to Massachusetts from Midway

Search for one-way flight options from Midway to Massachusetts. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 10, 2024.
If you're seeking multiple options on one-way flights from Chicago to Massachusetts, be sure to check out these deals, which are updated often. Those needing a return flight from Chicago to Massachusetts can use the search form above.
Wed 8/147:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/9$56
Thu 8/227:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/9$59
Tue 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/9$64
Mon 6/245:14 pmMDW - BDL
1 stop21h 03mFrontier
Deal found 6/9$64
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/9$65
Thu 6/206:56 amMDW - BDL
1 stop11h 52mFrontier
Deal found 6/9$65
Fri 9/67:59 pmMDW - BOS
1 stop9h 56mFrontier
Deal found 6/8$67
Tue 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/9$73
Wed 7/312:29 pmMDW - BOS
1 stop8h 58mFrontier
Deal found 6/9$75

Find flights from Midway to Massachusetts within your budget

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 3,020,828 searches. Data last updated June 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$96 - $294

Route

Depart

Return

Price

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 8/17

1 stop10h 26m

Boston Logan Intl

Sat 8/24

1 stop10h 03m

$96

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 8/17

1 stop10h 26m

Boston Logan Intl

Tue 8/27

1 stop7h 37m

$100

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Tue 8/13

1 stop10h 26m

Boston Logan Intl

Thu 8/15

1 stop7h 37m

$103

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/28

1 stop10h 26m

Boston Logan Intl

Wed 9/4

1 stop13h 39m

$104

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Thu 8/22

1 stop10h 26m

Boston Logan Intl

Mon 8/26

1 stop7h 53m

$106

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Tue 8/13

1 stop10h 26m

Boston Logan Intl

Tue 8/20

1 stop7h 37m

$108

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Mon 8/19

1 stop10h 26m

Boston Logan Intl

Mon 8/26

1 stop7h 53m

$114

Chicago MidwayHartford Bradley Intl

MDW - BDL

MDWBDL

Chicago Midway

Sat 8/17

1 stop4h 28m

Hartford Bradley Intl

Wed 11/20

1 stop3h 56m

$291

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/11

1 stop12h 12m

Boston Logan Intl

Mon 10/14

1 stop5h 23m

$294

Flights are sorted by cheapest first

Deals found on 6/9

No data available for this route at this time. Please check back soon.

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.

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 June 10, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Frontier, Delta and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,897 reviews
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,295 reviews
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Air Transat
7.7
Good
461 reviews
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.5
Good
991 reviews
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Porter Airlines
7.4
Good
382 reviews
Southwest
8.2
Very good
5,897 reviews

Boarding

8.3

Food

7.3

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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.

  • Can I find flights from Chicago Midway Airport to Massachusetts for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Massachusetts for under $100. The cheapest flight booked recently is on Frontier for just $96, but on average you can expect to pay $122.

  • Are there nonstop flights from Chicago Midway Airport to Massachusetts for under $500 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago Midway Airport to Massachusetts under $500. A good price for a nonstop flight from Chicago Midway Airport to Massachusetts is less than $460.

  • Are there last-minute flights available from Chicago Midway Airport to Massachusetts for under $200?

    There are currently 20+ open flights from Chicago Midway Airport to Massachusetts within the next 7 days for less than $200.

  • 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 does MDW to BOS mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to Boston Logan Intl Airport flight would often be abbreviated as a MDW to BOS flight. Nantucket Memorial Airport (ACK), West Tisbury Martha's Vineyard Airport (MVY), Worcester Airport (ORH), Hyannis Barnstable Airport (HYA), Boston Harbor SPB Airport (BNH) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Midway to Massachusetts that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Massachusetts flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Massachusetts with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Massachusetts flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Massachusetts that allow pets onboard?

    Many airlines flying from Midway to Massachusetts offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Massachusetts?

    Yes, you can often find last-minute deals on Midway to Massachusetts flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Massachusetts flight deals updated?

    The Chicago Midway Airport to Massachusetts flight deals you see on this page were last updated on 6/9.

  • What are the most popular airlines that fly from Chicago Midway Airport to Massachusetts?

    The most popular airlines flying from Chicago Midway Airport to Massachusetts are Delta, Frontier and United Airlines. Something to consider prior to booking your flight.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $218). Flying from Chicago Midway Airport to Massachusetts in July is currently the most expensive (average of $328). 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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Top 3 airlines flying from Midway to Massachusetts

Discover the top 3 airlines 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 3,020,828 searches. Data last updated June 10, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$409FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$84Average$326FlexibilityNo cancel feeOn-time69%
FrontierCheapest$84Average$168FlexibilityNo cancel feeOn-time62%
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Fort Lauderdale to Atlanta flights
Miami to Rome flights
Los Angeles to London flights
Philadelphia to Orlando flights
New York to Denver flights
Tampa to Key West flights
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Chicago Midway Airport to Maryland flights

Search flights from Midway to Massachusetts by cabin class

Find flights from Midway to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Midway to Massachusetts

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 June 10, 2024.
6%of flight departuresEarly morningMidnight to 6 am
36%of flight departuresMorning6 am to noon
41%of flight departuresAfternoonNoon to 6 pm
17%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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