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$75+ 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
Mar 3 — Mar 101
Mon 3/3
Mon 3/10
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 February 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Southwest)

One-way from

$75
(Southwest)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$212 or less

Good one-way deal

$126 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. 14% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 26, 2025.

This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/147:35 amMDW - BOS
Nonstop2h 15mSouthwest
Mon 3/246:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 2/26$151
This Delta deal was found by Cheapflights users on 2/26. 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.
Mon 3/242:55 pmMDW - BOS
1 stop3h 59mDelta
Mon 3/315:30 amBOS - MDW
1 stop4h 15mDelta
Deal found 2/26$167
This Southwest deal was found by Cheapflights users on 2/25. 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 3/278:35 pmMDW - ALB
Nonstop1h 55mSouthwest
Mon 3/316:45 amALB - MDW
Nonstop2h 20mSouthwest
Deal found 2/25$208
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/245:45 amMDW - BDL
1 stop4h 20mSouthwest
Tue 4/295:55 amBDL - MDW
Nonstop2h 25mSouthwest
Deal found 2/26$225
This Frontier deal was found by Cheapflights users on 2/26. 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.
Sat 3/154:40 pmMDW - BOS
1 stop7h 04mFrontier
Mon 3/175:10 amBOS - MDW
1 stop7h 24mFrontier
Deal found 2/26$244
This CheapOair deal was found by Cheapflights users on 2/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/76:20 amMDW - BDL
1 stop8h 12mFrontier
Sat 3/812:02 pmBDL - MDW
1 stop8h 33mFrontier
Deal found 2/26$244
This Delta deal was found by Cheapflights users on 2/26. 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.
Tue 4/86:00 amMDW - BDL
1 stop6h 16mDelta
Mon 4/144:59 pmBDL - MDW
1 stop6h 27mDelta
Deal found 2/26$259
This Delta deal was found by Cheapflights users on 2/26. 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.
Tue 4/86:42 pmMDW - ALB
1 stop3h 39mDelta
Tue 4/1512:30 pmALB - MDW
1 stop6h 50mDelta
Deal found 2/26$288
This Delta deal was found by Cheapflights users on 2/25. 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 5/306:00 amMDW - ACK
2 stops7h 59mDelta
Mon 6/212:05 pmACK - MDW
2 stops7h 40mDelta
Deal found 2/25$879

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 February 26, 2025.

Fly from

Midway

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/14

7:35 am-10:50 am

Nonstop2h 15m

Boston Logan Intl

Mon 3/24

6:30 am-8:15 am

Nonstop2h 45m

$151

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 3/24

2:55 pm-7:54 pm

1 stop3h 59m

Boston Logan Intl

Mon 3/31

5:30 am-8:45 am

1 stop4h 15m

$167

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Thu 3/27

8:35 pm-11:30 pm

Nonstop1h 55m

Albany Intl

Mon 3/31

6:45 am-8:05 am

Nonstop2h 20m

$208

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 4/24

5:45 am-11:05 am

1 stop4h 20m

Hartford Bradley Intl

Tue 4/29

5:55 am-7:20 am

Nonstop2h 25m

$225

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/15

4:40 pm-12:44 am

1 stop7h 04m

Boston Logan Intl

Mon 3/17

5:10 am-11:34 am

1 stop7h 24m

$244

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 6/5

9:12 pm-10:53 am

1 stop12h 41m

Hartford Bradley Intl

Sun 6/8

3:46 pm-11:55 pm

1 stop9h 09m

$244

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 4/8

6:00 am-1:16 pm

1 stop6h 16m

Hartford Bradley Intl

Mon 4/14

4:59 pm-10:26 pm

1 stop6h 27m

$259

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 4/8

6:42 pm-11:21 pm

1 stop3h 39m

Albany Intl

Tue 4/15

12:30 pm-6:20 pm

1 stop6h 50m

$288

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Fri 5/30

6:00 am-2:59 pm

2 stops7h 59m

Nantucket Memorial

Mon 6/2

12:05 pm-6:45 pm

2 stops7h 40m

$879

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 5/6

6:50 pm-9:45 pm

Nonstop1h 55m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

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 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 February 26, 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 February 26, 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
8.1
Very good
4,369 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,369 reviews
Southwest
8.1
Very good
4,369 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,151 reviews
Southwest
8.1
Very good
4,369 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Allegiant Air
7.3
Good
759 reviews
Southwest
8.1
Very good
4,369 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Frontier
6.0
Okay
3,337 reviews
Southwest
8.1
Very good
4,369 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 $75. Delta flights start at $84 while deals on Allegiant Air start at $109 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 $234, our data indicates the cheapest price to be $78. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $145.

  • 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 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 2,558,603 searches. Data last updated February 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$366FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$116FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$286FlexibilityNo cancel feeOn-time63%
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