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$69+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

April

Cheapest in

August

Average price

$225

Good round-trip deal

$137 or less

Good one-way deal

$68 or less
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. 9% potential increase in price ($22 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 July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 8/165:40 pmMDW - BOS
Nonstop2h 20mSouthwest
Wed 8/205:40 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 7/2$137
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/109:12 pmMDW - BOS
1 stop10h 23mFrontier
Sat 7/129:40 amBOS - MDW
1 stop11h 42mFrontier
Deal found 7/1$149
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:48 amMDW - BDL
1 stop9h 14mFrontier
Sun 9/148:47 pmBDL - MDW
1 stop11h 46mFrontier
Deal found 7/2$207
This Southwest deal was found by Cheapflights users on 7/2. 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 8/146:30 amMDW - BDL
2 stops9h 05mSouthwest
Sun 8/175:35 amBDL - MDW
Nonstop2h 20mSouthwest
Deal found 7/2$212
This eDestinos deal was found by Cheapflights users on 7/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:12 amMDW - BOS
1 stop25h 49mAllegiant Air
Sun 7/2011:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Deal found 7/1$221
This Delta deal was found by Cheapflights users on 7/1. 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 7/156:20 pmMDW - BDL
1 stop3h 41mDelta
Tue 7/295:35 amBDL - MDW
1 stop4h 09mDelta
Deal found 7/1$227
This Delta deal was found by Cheapflights users on 7/2. 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 8/136:04 amMDW - ACK
2 stops9h 05mDelta
Wed 8/2012:06 pmACK - MDW
2 stops10h 38mDelta
Deal found 7/2$249
This Southwest deal was found by Cheapflights users on 7/3. 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.
Wed 8/201:00 pmMDW - ALB
2 stops8h 10mSouthwest
Sun 8/246:50 amALB - MDW
1 stop7h 15mSouthwest
Deal found 7/3$278
This Delta deal was found by Cheapflights users on 7/1. 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 8/156:17 pmMDW - ALB
1 stop4h 04mDelta
Fri 8/226:00 amALB - MDW
1 stop3h 35mDelta
Deal found 7/1$287

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 July 3, 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

Sat 8/16

5:40 pm-9:00 pm

Nonstop2h 20m

Boston Logan Intl

Wed 8/20

5:40 pm-7:20 pm

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 7/10

9:12 pm-8:35 am

1 stop10h 23m

Boston Logan Intl

Sat 7/12

9:40 am-8:22 pm

1 stop11h 42m

$149

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 9/12

9:48 am-8:02 pm

1 stop9h 14m

Hartford Bradley Intl

Sun 9/14

8:47 pm-7:33 am

1 stop11h 46m

$207

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 8/14

6:30 am-4:35 pm

2 stops9h 05m

Hartford Bradley Intl

Sun 8/17

5:35 am-6:55 am

Nonstop2h 20m

$212

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 7/18

9:12 am-12:01 pm

1 stop25h 49m

Boston Logan Intl

Sun 7/20

11:31 am-7:13 am

1 stop20h 42m

$221

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 7/15

6:20 pm-11:01 pm

1 stop3h 41m

Hartford Bradley Intl

Thu 7/24

5:35 am-8:44 am

1 stop4h 09m

$227

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

Wed 8/13

6:04 am-4:09 pm

2 stops9h 05m

Nantucket Memorial

Wed 8/20

12:06 pm-9:44 pm

2 stops10h 38m

$249

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 10/3

8:30 pm-11:20 pm

Nonstop1h 50m

Albany Intl

Sun 10/5

4:10 pm-11:10 pm

1 stop8h 00m

$277

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 8/15

6:17 pm-11:21 pm

1 stop4h 04m

Albany Intl

Fri 8/22

6:00 am-8:35 am

1 stop3h 35m

$287

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 7/30

7:35 am-10:50 am

Nonstop2h 15m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 20 results
1
2

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 June is currently the most expensive (average of $306). 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 July 3, 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.

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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and Allegiant Air from Chicago Midway Airport to Massachusetts have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $69. Frontier flights start at $70 while deals on Delta start at $99 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 $176, our data indicates the cheapest price to be $68. The most popular route (Chicago Midway - Boston Logan Intl), is priced around $137.

  • 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 June is currently the most expensive (average of $306). 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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Midway to Minneapolis flights
Midway to Miami flights
Midway to Philadelphia flights
O'Hare Intl to Kalispell flights

Top 2 airlines flying from Midway to Massachusetts

Discover the top 2 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$153Average$289FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$297FlexibilityNo cancel feeOn-time69%

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