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Midway

$59+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$127
(Southwest)

One-way from

$68
(Southwest)

Popular in

May

Cheapest in

September

Average price

$275

Good round-trip deal

$174 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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 ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/313:00 pmBOS - MDW
1 stop7h 50mSouthwest
Thu 7/36:00 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/21$127
This Frontier deal was found by Cheapflights users on 4/22. 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 5/2810:45 amBOS - MDW
1 stop12h 51mFrontier
Sun 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/22$188
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Mon 7/72:54 pmMDW - BOS
1 stop17h 21mAllegiant Air
Deal found 4/21$225
This Mytrip deal was found by Cheapflights users on 4/22. 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.
Thu 6/1211:31 amBOS - MDW
1 stop20h 44mMultiple Airlines
Mon 6/168:36 pmMDW - BOS
3 stops35h 27mMultiple Airlines
Deal found 4/22$249
This Southwest deal was found by Cheapflights users on 4/22. 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 7/44:35 pmALB - MDW
Nonstop2h 10mSouthwest
Fri 7/118:10 pmMDW - ALB
Nonstop1h 55mSouthwest
Deal found 4/22$267
This Delta deal was found by Cheapflights users on 4/22. 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 5/296:00 amALB - MDW
1 stop3h 40mDelta
Sat 5/315:25 pmMDW - ALB
1 stop3h 53mDelta
Deal found 4/22$269
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/245:50 pmBDL - MDW
Nonstop2h 25mSouthwest
Sun 5/251:40 pmMDW - BDL
Nonstop2h 05mSouthwest
Deal found 4/21$273
This Frontier deal was found by Cheapflights users on 4/22. 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 5/223:56 pmBDL - MDW
1 stop7h 00mFrontier
Sun 5/256:10 amMDW - BDL
1 stop7h 52mFrontier
Deal found 4/22$280
This Delta deal was found by Cheapflights users on 4/22. 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 5/215:35 amBDL - MDW
1 stop4h 05mDelta
Sun 5/256:25 pmMDW - BDL
1 stop3h 30mDelta
Deal found 4/22$298
This Delta deal was found by Cheapflights users on 4/22. 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.
Sun 10/125:40 amBOS - MDW
1 stop8h 29mDelta
Wed 10/229:30 amMDW - BOS
1 stop5h 18mDelta
Deal found 4/22$317
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/193:54 pmBDL - MDW
2 stops23h 09mMultiple Airlines
Sun 6/228:09 pmMDW - BDL
3 stops36h 00mMultiple Airlines
Deal found 4/21$491

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 April 22, 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

Sat 5/31

3:00 pm-9:50 pm

1 stop7h 50m

Chicago Midway

Thu 7/3

6:00 am-9:15 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/28

10:45 am-10:36 pm

1 stop12h 51m

Chicago Midway

Sun 6/1

9:12 pm-8:35 am

1 stop10h 23m

$188

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 7/3

11:31 am-7:13 am

1 stop20h 42m

Chicago Midway

Mon 7/7

2:54 pm-9:15 am

1 stop17h 21m

$225

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 6/12

11:31 am-7:15 am

1 stop20h 44m

Chicago Midway

Mon 6/16

8:36 pm-9:03 am

3 stops35h 27m

$249

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Fri 7/4

4:35 pm-5:45 pm

Nonstop2h 10m

Chicago Midway

Fri 7/11

8:10 pm-11:05 pm

Nonstop1h 55m

$267

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 5/29

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Sat 5/31

5:25 pm-10:18 pm

1 stop3h 53m

$269

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/29

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Wed 6/4

8:10 pm-11:15 pm

Nonstop2h 05m

$278

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 5/21

5:35 am-8:40 am

1 stop4h 05m

Chicago Midway

Sun 5/25

6:25 pm-10:55 pm

1 stop3h 30m

$298

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/22

3:56 pm-9:56 pm

1 stop7h 00m

Chicago Midway

Fri 5/23

9:12 pm-7:31 pm

1 stop21h 19m

$301

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 10/12

5:40 am-1:09 pm

1 stop8h 29m

Chicago Midway

Sat 10/18

3:40 pm-10:41 pm

1 stop6h 01m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 23 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 April 22, 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.

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 April 22, 2025.
Read reviews from past customers who have flown Southwest, Delta and Allegiant Air from Massachusetts to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $68. Users have also found prices from $93 and $95 on Allegiant Air and Frontier, 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 $259, our data shows the cheapest flight currently is $48. 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 Massachusetts?

Book flights to Massachusetts if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
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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Cleveland to O'Hare Intl flights
Philadelphia to Midway flights
Oakland to O'Hare Intl flights
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Sacramento 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$97Average$245FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$168FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$139Average$259FlexibilityNo cancel feeOn-time63%
DeltaCheapest$237Average$408FlexibilityNo cancel feeOn-timeN/A

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