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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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$68
(Southwest)

Popular in

April

Cheapest in

September

Average price

$289

Good round-trip deal

$179 or less

Good one-way deal

$78 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. 11% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/16. 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.
Fri 5/27:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 5/47:40 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 4/16$117
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/84:00 pmMDW - BOS
1 stop16h 34mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 4/16$191
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Fri 6/68:36 pmMDW - BOS
1 stop11h 36mAllegiant Air
Sun 6/811:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Deal found 4/17$211
This Frontier deal was found by Cheapflights users on 4/17. 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.
Sun 6/16:20 amMDW - BDL
1 stop7h 46mFrontier
Sun 6/812:38 pmBDL - MDW
1 stop11h 40mFrontier
Deal found 4/17$240
This Southwest deal was found by Cheapflights users on 4/17. 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 6/177:35 pmMDW - ALB
Nonstop1h 55mSouthwest
Tue 6/246:30 amALB - MDW
Nonstop2h 10mSouthwest
Deal found 4/17$253
This Delta deal was found by Cheapflights users on 4/17. 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.
Fri 5/166:25 pmMDW - ALB
1 stop3h 49mDelta
Tue 5/206:00 amALB - MDW
1 stop3h 40mDelta
Deal found 4/17$273
This Delta deal was found by Cheapflights users on 4/17. 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.
Fri 5/309:20 amMDW - BDL
1 stop7h 53mDelta
Sat 5/315:35 amBDL - MDW
1 stop4h 05mDelta
Deal found 4/17$293
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:25 pmMDW - BOS
1 stop4h 21mDelta
Wed 5/285:20 amBOS - MDW
1 stop8h 08mDelta
Deal found 4/16$295
This Southwest deal was found by Cheapflights users on 4/17. 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 5/241:55 pmMDW - BDL
Nonstop2h 05mSouthwest
Mon 5/265:30 amBDL - MDW
Nonstop2h 25mSouthwest
Deal found 4/17$296
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:05 amMDW - BDL
1 stop27h 20mMultiple Airlines
Sun 6/812:27 pmBDL - MDW
2 stops32h 19mMultiple Airlines
Deal found 4/16$388
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:00 amMDW - ACK
2 stops9h 07mDelta
Wed 7/911:35 amACK - MDW
2 stops7h 53mDelta
Deal found 4/16$499

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 April 17, 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 5/2

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

Sun 5/4

7:40 am-9:15 am

Nonstop2h 35m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

4:00 pm-9:34 am

1 stop16h 34m

Boston Logan Intl

Wed 5/14

8:00 am-12:24 pm

1 stop29h 24m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/6

8:36 pm-9:12 am

1 stop11h 36m

Boston Logan Intl

Sun 6/8

11:31 am-7:15 am

1 stop20h 44m

$211

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sun 6/1

6:20 am-3:06 pm

1 stop7h 46m

Hartford Bradley Intl

Sun 6/8

12:38 pm-11:18 pm

1 stop11h 40m

$240

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 6/17

7:35 pm-10:30 pm

Nonstop1h 55m

Albany Intl

Tue 6/24

6:30 am-7:40 am

Nonstop2h 10m

$253

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 5/16

6:25 pm-11:14 pm

1 stop3h 49m

Albany Intl

Tue 5/20

6:00 am-8:40 am

1 stop3h 40m

$273

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 5/30

9:20 am-6:13 pm

1 stop7h 53m

Hartford Bradley Intl

Sat 5/31

5:35 am-8:40 am

1 stop4h 05m

$293

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 5/14

6:25 pm-11:46 pm

1 stop4h 21m

Boston Logan Intl

Wed 5/28

5:20 am-12:28 pm

1 stop8h 08m

$295

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 5/24

1:55 pm-5:00 pm

Nonstop2h 05m

Hartford Bradley Intl

Mon 5/26

5:30 am-6:55 am

Nonstop2h 25m

$296

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 6/6

8:05 am-12:25 pm

1 stop27h 20m

Hartford Bradley Intl

Sun 6/8

12:27 pm-7:46 pm

2 stops32h 19m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 25 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, 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.

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 April 17, 2025.

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 April 17, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Southwest, Delta and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $68. Allegiant Air flights start at $96 while deals on Frontier start at $105 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 $219, our data indicates the cheapest price to be $48. 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, 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$366FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$116FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$157Average$297FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$292FlexibilityNo cancel feeOn-time63%

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