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Midway

$69+ Cheap flights from Massachusetts to Midway (MDW)

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Massachusetts to Midway

Keep the following information in mind while searching for Massachusetts to Midway flight deals. Data was last updated July 29, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

September

Average price

$227

Good round-trip deal

$159 or less

Good one-way deal

$153 or less
From Massachusetts to Chicago Midway
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One-way flight from Massachusetts to Chicago Midway
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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 ($4 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 Massachusetts to Chicago Midway.
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Price to beat on a one-way flight from Massachusetts to Chicago Midway.
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Find flight deals from Massachusetts to Midway

Cheapest flights from Massachusetts to Midway
Explore the most affordable flight options available from Massachusetts to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/199:05 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 7/28$137
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:00 amBDL - MDW
1 stop6h 10mSouthwest
Tue 9/166:10 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 7/28$187
This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 8/215:35 amBDL - MDW
1 stop4h 00mDelta
Tue 8/261:08 pmMDW - BDL
1 stop3h 38mDelta
Deal found 7/28$197
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/169:40 amBOS - MDW
1 stop11h 42mFrontier
Sun 8/173:58 pmMDW - BOS
1 stop7h 40mFrontier
Deal found 7/27$208
This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:30 amBDL - MDW
1 stop6h 28mFrontier
Mon 9/298:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 7/28$218
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:15 pmALB - MDW
Nonstop2h 10mSouthwest
Fri 8/226:20 pmMDW - ALB
Nonstop2h 00mSouthwest
Deal found 7/28$249
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 9/106:00 amALB - MDW
1 stop3h 35mDelta
Wed 9/176:15 pmMDW - ALB
1 stop4h 05mDelta
Deal found 7/27$253

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Midway 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 29, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago Midway Airport that are best for you.

Fly from

Massachusetts

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/17

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sun 10/19

6:05 am-9:20 am

Nonstop2h 15m

$137

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 9/13

6:00 am-11:10 am

1 stop6h 10m

Chicago Midway

Tue 9/16

6:10 pm-9:20 pm

Nonstop2h 10m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/21

5:35 am-8:35 am

1 stop4h 00m

Chicago Midway

Tue 8/26

1:08 pm-5:46 pm

1 stop3h 38m

$197

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/16

9:40 am-8:22 pm

1 stop11h 42m

Chicago Midway

Sun 8/17

3:58 pm-12:38 am

1 stop7h 40m

$208

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$209

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/25

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

Fri 10/3

9:48 am-7:57 pm

1 stop9h 09m

$218

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 8/19

6:15 pm-7:25 pm

Nonstop2h 10m

Chicago Midway

Fri 8/22

6:20 pm-9:20 pm

Nonstop2h 00m

$249

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

6:49 pm-4:43 pm

2 stops22h 54m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$251

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 9/10

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Wed 9/17

6:15 pm-11:20 pm

1 stop4h 05m

$253

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/19

8:20 pm-9:55 pm

Nonstop2h 35m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 19 results
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Best time to book a flight from Massachusetts to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Massachusetts 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 Massachusetts to Chicago Midway Airport

What is the cheapest month to book a flight from Massachusetts to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $160). Flying from Massachusetts to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 MA to MDW?

Find hourly flight availability from Massachusetts to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

When flying from Massachusetts to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 29, 2025.
See what other customers who have flown with Southwest, Delta, and Allegiant Air from Massachusetts to Chicago Midway Airport 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
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Midway. 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 Massachusetts to Chicago Midway Airport one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $69. Users have also found prices from $97 and $99 on Frontier and Delta, respectively.

  • What are the most popular routes from Massachusetts to Chicago Midway Airport?

    The most popular route from Massachusetts to Chicago Midway Airport is Boston Logan Intl - Chicago Midway. You may also consider Hartford Bradley Intl - Chicago Midway or Albany Intl - Chicago Midway.

  • What are the cheapest flights from Massachusetts to Chicago Midway Airport?

    While on average a flight from Massachusetts to Chicago Midway Airport is generally $251, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $117 for that flight.

  • Can I find deals for flights from Massachusetts to Midway that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Midway.

  • Can I find deals for business class flights from Massachusetts to Midway?

    Yes. Cheapflights offers flight deals from Massachusetts to Midway 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 Massachusetts to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $160). Flying from Massachusetts to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Massachusetts to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Salt Lake City to O'Hare Intl flights

Top 5 airlines flying from Massachusetts to Midway

Discover the top 5 airlines that operate flights from Massachusetts to Midway. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$97Average$177FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$124FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$125Average$254FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$187Average$259FlexibilityNo cancel feeOn-time71%
DeltaCheapest$227Average$357FlexibilityNo cancel feeOn-timeN/A

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