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$79+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Massachusetts to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Midway (MDW). 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 December 22, 2024.

Round-trip from

$138
(Frontier)

One-way from

$79
(Southwest)
From Massachusetts to Chicago Midway
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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 December 22, 2024.

This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:45 amBOS - MDW
1 stop10h 26mFrontier
Tue 1/75:24 pmMDW - BOS
1 stop6h 06mFrontier
Deal found 12/21$178
This Southwest deal was found by Cheapflights users on 12/21. 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.
Tue 12/3112:20 pmBOS - MDW
1 stop7h 25mSouthwest
Sun 1/56:25 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/21$284
This Delta deal was found by Cheapflights users on 12/20. 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 12/314:59 pmBDL - MDW
1 stop6h 07mDelta
Tue 1/75:07 pmMDW - BDL
1 stop5h 52mDelta
Deal found 12/20$314
This Southwest deal was found by Cheapflights users on 12/20. 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.
Tue 12/316:15 pmBDL - MDW
Nonstop2h 35mSouthwest
Tue 1/712:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 12/20$330
This Delta deal was found by Cheapflights users on 12/21. 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 12/244:40 pmBOS - MDW
1 stop6h 26mDelta
Fri 12/275:04 pmMDW - BOS
1 stop5h 55mDelta
Deal found 12/21$346
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/276:05 pmBDL - MDW
1 stop6h 09mFrontier
Mon 12/308:25 amMDW - BDL
1 stop7h 40mFrontier
Deal found 12/21$378
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:45 amALB - MDW
1 stop4h 05mDelta
Sat 1/49:30 amMDW - ALB
1 stop6h 05mDelta
Deal found 12/21$390
This Southwest deal was found by Cheapflights users on 12/21. 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.
Tue 12/317:35 amALB - MDW
Nonstop2h 15mSouthwest
Sat 1/49:55 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 12/21$427
This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:45 amBOS - MDW
3 stops39h 24mMultiple Airlines
Thu 12/267:17 amMDW - BOS
1 stop24h 08mMultiple Airlines
Deal found 12/21$1,704

Find flights from Massachusetts to Midway within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/6

11:55 am-11:20 pm

1 stop12h 25m

Chicago Midway

Fri 1/10

3:37 pm-12:30 am

1 stop7h 53m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/15

8:10 am-10:05 am

Nonstop2h 55m

Chicago Midway

Tue 1/21

6:25 pm-9:40 pm

Nonstop2h 15m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/11

3:50 pm-11:29 pm

1 stop8h 39m

Chicago Midway

Sun 1/12

7:45 am-2:40 pm

1 stop29h 55m

$210

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 1/28

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Tue 2/4

9:33 am-4:09 pm

1 stop5h 36m

$276

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/9

6:00 am-7:45 am

Nonstop2h 45m

Chicago Midway

Mon 1/13

12:25 pm-3:25 pm

Nonstop2h 00m

$297

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 1/20

7:05 am-8:35 am

Nonstop2h 30m

Chicago Midway

Mon 1/27

1:45 pm-4:35 pm

Nonstop1h 50m

$300

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 1/21

6:06 am-11:59 am

1 stop6h 53m

Chicago Midway

Fri 1/24

6:28 pm-11:27 pm

1 stop3h 59m

$303

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/11

9:15 am-4:12 pm

1 stop7h 57m

Chicago Midway

Sun 1/12

6:28 pm-11:43 pm

1 stop4h 15m

$315

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 3/22

12:02 pm-7:35 pm

1 stop8h 33m

Chicago Midway

Sun 3/30

7:25 am-6:48 pm

1 stop10h 23m

$708

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/18

5:50 am-7:50 am

Nonstop3h 00m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 20 results
1
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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.

Travel insights for flights from Massachusetts to Midway

Get recent, data-driven insights about flights from Massachusetts to Midway including ideal travel times, pricing trends, and more.

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 December 22, 2024.

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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 23.0 F).

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 December 22, 2024.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Massachusetts to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
823 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,472 reviews
Southwest
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $79. Users have also found prices from $80 and $120 on Frontier and Allegiant Air, 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 $352, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $144 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.

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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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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$150FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$147Average$336FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$237FlexibilityNo cancel feeOn-time63%
DeltaCheapest$315Average$439FlexibilityNo cancel feeOn-timeN/A
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