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$79+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Jan 2 — Jan 91
Thu 1/2
Thu 1/9
1 adult, Economy
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Cheap flight deals from Midway to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 28, 2024.

Round-trip from

$132
(Frontier)

One-way from

$79
(Southwest)
From Chicago Midway to Massachusetts
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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 December 28, 2024.

This Orbitz deal was found by Cheapflights users on 12/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:59 pmMDW - BOS
1 stop8h 02mFrontier
Mon 1/66:00 amBOS - MDW
1 stop8h 24mFrontier
Deal found 12/28$235
This Southwest deal was found by Cheapflights users on 12/27. 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 12/307:00 pmMDW - BOS
1 stop4h 20mSouthwest
Sat 1/48:15 pmBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/27$322
This Frontier deal was found by Cheapflights users on 12/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:25 amMDW - BDL
1 stop7h 40mFrontier
Wed 1/14:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 12/26$338
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:51 pmMDW - BOS
1 stop5h 00mDelta
Sat 1/412:20 pmBOS - MDW
1 stop5h 04mDelta
Deal found 12/28$346
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/286:25 pmMDW - BDL
1 stop3h 47mDelta
Thu 1/91:00 pmBDL - MDW
1 stop6h 14mDelta
Deal found 12/26$676
This Southwest deal was found by Cheapflights users on 12/27. 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 12/308:30 pmMDW - ALB
Nonstop1h 50mSouthwest
Fri 1/37:00 amALB - MDW
Nonstop2h 20mSouthwest
Deal found 12/27$695
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:30 amMDW - ALB
1 stop6h 05mDelta
Mon 1/612:40 pmALB - MDW
1 stop6h 34mDelta
Deal found 12/27$713
This Southwest deal was found by Cheapflights users on 12/27. 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 12/308:40 pmMDW - BDL
Nonstop2h 00mSouthwest
Fri 1/36:45 amBDL - MDW
Nonstop2h 30mSouthwest
Deal found 12/27$869

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 2,558,603 searches. Data last updated December 28, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 2/16

12:43 pm-12:44 am

1 stop11h 01m

Boston Logan Intl

Mon 3/3

11:11 am-9:14 pm

1 stop11h 03m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 2/10

6:15 am-12:39 am

1 stop17h 24m

Boston Logan Intl

Mon 2/17

7:00 pm-7:32 am

1 stop13h 32m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 2/2

7:00 pm-10:15 pm

Nonstop2h 15m

Boston Logan Intl

Mon 2/3

8:10 am-10:05 am

Nonstop2h 55m

$158

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Thu 1/16

12:05 pm-2:55 pm

Nonstop1h 50m

Albany Intl

Tue 1/21

5:45 am-7:15 am

Nonstop2h 30m

$280

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 1/17

2:08 pm-8:04 pm

1 stop4h 56m

Boston Logan Intl

Sun 1/19

5:35 am-10:36 am

1 stop6h 01m

$316

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 1/21

2:25 pm-10:05 pm

2 stops6h 40m

Hartford Bradley Intl

Sun 1/26

1:30 pm-10:00 pm

1 stop9h 30m

$321

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 2/28

6:00 am-1:18 pm

1 stop6h 18m

Hartford Bradley Intl

Sun 3/2

6:00 am-12:42 pm

1 stop7h 42m

$342

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 1/10

6:00 am-1:16 pm

1 stop6h 16m

Albany Intl

Sun 1/12

12:40 pm-6:14 pm

1 stop6h 34m

$402

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Tue 6/3

6:00 am-3:14 pm

2 stops8h 14m

Nantucket Memorial

Sat 6/7

11:35 am-9:46 pm

2 stops11h 11m

$808

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 2/2

8:40 am-11:55 am

Nonstop2h 15m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 22 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.

Travel insights for flights from Midway to Massachusetts

Get recent, data-driven insights about flights from Midway to Massachusetts including ideal travel times, pricing trends, and more.

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 December 28, 2024.

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.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 December 28, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Frontier, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,731 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,731 reviews
Southwest
8.1
Very good
4,731 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,556 reviews
Southwest
8.1
Very good
4,731 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
814 reviews
Southwest
8.1
Very good
4,731 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,459 reviews
Southwest
8.1
Very good
4,731 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Massachusetts one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $79. Frontier flights start at $81 while deals on Delta start at $139 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 $215, our data indicates the cheapest price to be $79. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $124.

  • 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, 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 $311). 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.

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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 4 airlines flying from Midway to Massachusetts

Discover the top 4 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 2,558,603 searches. Data last updated December 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$394FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$122FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$153Average$276FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$293FlexibilityNo cancel feeOn-time69%
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