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$96+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$96
(Mytrip)

Popular in

May

Cheapest in

September

Average price

$279

Good round-trip deal

$231 or less

Good one-way deal

$129 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. 11% potential increase in price ($31 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 March 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 March 31, 2025.

This Southwest deal was found by Cheapflights users on 3/31. 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 6/207:00 amBOS - MDW
Nonstop2h 40mSouthwest
Mon 6/236:55 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 3/31$157
This Frontier deal was found by Cheapflights users on 3/31. 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 5/812:59 pmBOS - MDW
1 stop8h 34mFrontier
Sun 5/1110:55 amMDW - BOS
1 stop13h 10mFrontier
Deal found 3/31$198
This Frontier deal was found by Cheapflights users on 3/29. 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 5/153:28 pmBDL - MDW
1 stop9h 11mFrontier
Sun 5/1810:55 amMDW - BDL
1 stop7h 19mFrontier
Deal found 3/29$228
This eDestinos deal was found by Cheapflights users on 3/31. 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.
Thu 4/106:00 amBOS - MDW
1 stop14h 35mMultiple Airlines
Sun 4/132:19 pmMDW - BOS
1 stop20h 43mMultiple Airlines
Deal found 3/31$235
This Southwest deal was found by Cheapflights users on 3/31. 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 6/42:40 pmALB - MDW
1 stop7h 40mSouthwest
Sat 6/77:05 pmMDW - ALB
Nonstop1h 55mSouthwest
Deal found 3/31$263
This Delta deal was found by Cheapflights users on 3/30. 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 4/236:05 amALB - MDW
1 stop3h 35mDelta
Tue 4/295:59 pmMDW - ALB
1 stop4h 22mDelta
Deal found 3/30$273
This Southwest deal was found by Cheapflights users on 3/30. 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 5/256:35 amMDW - BDL
1 stop8h 05mSouthwest
Deal found 3/30$289
This Delta deal was found by Cheapflights users on 3/31. 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 7/16:00 amBDL - MDW
1 stop6h 56mDelta
Sat 7/55:53 pmMDW - BDL
1 stop4h 03mDelta
Deal found 3/31$293
This Delta deal was found by Cheapflights users on 3/31. 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.
Sat 6/149:00 amBOS - MDW
1 stop7h 39mDelta
Mon 6/166:25 pmMDW - BOS
1 stop4h 27mDelta
Deal found 3/31$330

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 March 31, 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 6/20

7:00 am-8:40 am

Nonstop2h 40m

Chicago Midway

Mon 6/23

6:55 pm-10:10 pm

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/8

12:59 pm-8:33 pm

1 stop8h 34m

Chicago Midway

Sun 5/11

10:55 am-1:05 am

1 stop13h 10m

$198

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/15

3:28 pm-11:39 pm

1 stop9h 11m

Chicago Midway

Sun 5/18

10:55 am-7:14 pm

1 stop7h 19m

$228

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 4/10

6:00 am-7:35 pm

1 stop14h 35m

Chicago Midway

Sun 4/13

2:19 pm-12:02 pm

1 stop20h 43m

$235

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 5/24

2:20 pm-9:13 pm

1 stop7h 53m

Chicago Midway

Wed 5/28

6:25 pm-11:14 pm

1 stop3h 49m

$269

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 5/29

7:30 am-8:40 am

Nonstop2h 10m

Chicago Midway

Sun 6/1

8:40 pm-11:35 pm

Nonstop1h 55m

$279

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/24

5:50 pm-7:15 pm

Nonstop2h 25m

Chicago Midway

Sun 5/25

6:35 am-3:40 pm

1 stop8h 05m

$289

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

7:05 am-11:56 am

1 stop5h 51m

Chicago Midway

Fri 7/4

6:25 pm-10:57 pm

1 stop3h 32m

$293

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/14

9:00 am-3:39 pm

1 stop7h 39m

Chicago Midway

Mon 6/16

6:25 pm-11:52 pm

1 stop4h 27m

$330

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 6/12

11:31 am-7:15 am

1 stop20h 44m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 21 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 March 31, 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 March 31, 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
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Allegiant Air. According to our data, you can fly for as low as $96. Users have also found prices from $97 and $109 on Frontier and Southwest, 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 $273, 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 $97 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
New Buffalo
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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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$97Average$276FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$156FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$253FlexibilityNo cancel feeOn-time63%
DeltaCheapest$237Average$411FlexibilityNo cancel feeOn-timeN/A
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