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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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 21, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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.
Wed 12/1112:57 pmMDW - BOS
1 stop10h 33mFrontier
Wed 12/185:45 amBOS - MDW
1 stop8h 39mFrontier
Deal found 11/20$103
This Southwest deal was found by Cheapflights users on 11/21. 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 12/96:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Fri 12/136:40 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/21$158
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Mon 12/1611:33 amMDW - BDL
1 stop21h 19mFrontier
Wed 12/184:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 11/20$208
This Delta deal was found by Cheapflights users on 11/21. 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 12/175:50 pmMDW - BDL
1 stop4h 48mDelta
Wed 12/185:25 amBDL - MDW
1 stop4h 33mDelta
Deal found 11/21$276
This Southwest deal was found by Cheapflights users on 11/19. 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 12/1212:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Mon 12/167:30 amBDL - MDW
Nonstop2h 30mSouthwest
Deal found 11/19$288
This Delta deal was found by Cheapflights users on 11/19. 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 12/64:58 pmMDW - BOS
1 stop7h 24mDelta
Tue 12/108:50 amBOS - MDW
1 stop9h 11mDelta
Deal found 11/19$300
This Delta deal was found by Cheapflights users on 11/20. 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 12/245:51 pmMDW - ALB
1 stop4h 29mDelta
Sat 12/285:45 amALB - MDW
1 stop4h 05mDelta
Deal found 11/20$303
This Southwest deal was found by Cheapflights users on 11/20. 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 12/138:20 pmMDW - ALB
Nonstop1h 50mSouthwest
Sun 12/157:00 amALB - MDW
Nonstop2h 20mSouthwest
Deal found 11/20$330
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sun 11/246:41 pmMDW - ALB
2 stops19h 19mMultiple Airlines
Sat 11/3011:29 amALB - MDW
2 stops25h 17mMultiple Airlines
Deal found 11/19$889

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/11

12:57 pm-12:30 am

1 stop10h 33m

Boston Logan Intl

Wed 12/18

5:45 am-1:24 pm

1 stop8h 39m

$103

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/7

8:05 am-11:20 am

Nonstop2h 15m

Boston Logan Intl

Sun 12/8

6:40 am-8:25 am

Nonstop2h 45m

$158

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 12/16

11:33 am-9:52 am

1 stop21h 19m

Hartford Bradley Intl

Wed 12/18

4:00 pm-9:17 pm

1 stop6h 17m

$208

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 1/8

12:25 pm-3:25 pm

Nonstop2h 00m

Hartford Bradley Intl

Sun 1/12

6:55 pm-8:30 pm

Nonstop2h 35m

$268

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 12/17

4:58 pm-11:58 pm

1 stop6h 00m

Hartford Bradley Intl

Wed 12/18

5:25 am-8:58 am

1 stop4h 33m

$276

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Tue 12/24

5:51 pm-11:20 pm

1 stop4h 29m

Albany Intl

Sat 12/28

5:45 am-8:50 am

1 stop4h 05m

$303

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 12/3

9:31 am-3:50 pm

1 stop5h 19m

Boston Logan Intl

Fri 12/6

5:10 am-8:58 am

1 stop4h 48m

$316

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 12/13

8:20 pm-11:10 pm

Nonstop1h 50m

Albany Intl

Sun 12/15

7:00 am-8:20 am

Nonstop2h 20m

$330

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sun 12/22

6:31 pm-10:42 pm

2 stops27h 11m

Hartford Bradley Intl

Sat 12/28

6:00 am-8:45 am

2 stops27h 45m

$1,293

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 2/3

10:05 am-1:20 pm

Nonstop2h 15m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 21 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 November 21, 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 November 21, 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
5,005 reviews

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,536 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Food

7.2

Comfort

8.1

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $80 while deals on Delta start at $136 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 $203, our data indicates the cheapest price to be $62. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $158.

  • 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$422FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$122FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$153Average$270FlexibilityNo cancel feeOn-time63%
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