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$57+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(Frontier)

One-way from

$57
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$256

Good round-trip deal

$225 or less

Good one-way deal

$153 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. 14% potential increase in price ($40 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 February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/19. 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 3/215:10 amBOS - MDW
1 stop7h 24mFrontier
Mon 3/248:27 pmMDW - BOS
1 stop13h 06mFrontier
Deal found 2/19$152
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 2/276:50 amBOS - MDW
Nonstop2h 55mSouthwest
Tue 3/46:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 2/20$157
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 4/301:25 pmBDL - MDW
2 stops8h 45mSouthwest
Fri 5/29:50 amMDW - BDL
1 stop5h 25mSouthwest
Deal found 2/20$222
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 4/255:40 amBDL - MDW
1 stop4h 00mDelta
Mon 4/285:59 pmMDW - BDL
1 stop4h 11mDelta
Deal found 2/20$237
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/183:13 pmBDL - MDW
1 stop9h 37mFrontier
Mon 4/217:05 amMDW - BDL
1 stop6h 20mFrontier
Deal found 2/20$240
This Delta deal was found by Cheapflights users on 2/19. 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 4/159:05 amBOS - MDW
1 stop10h 15mDelta
Tue 4/223:02 pmMDW - BOS
1 stop7h 47mDelta
Deal found 2/19$263
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/202:30 pmALB - MDW
2 stops6h 20mSouthwest
Thu 3/277:15 amMDW - ALB
1 stop5h 25mSouthwest
Deal found 2/20$272
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 3/236:00 amALB - MDW
1 stop3h 45mDelta
Sat 3/299:25 amMDW - ALB
1 stop5h 50mDelta
Deal found 2/20$283
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:10 amBOS - MDW
2 stops38h 04mMultiple Airlines
Sun 6/17:26 pmMDW - BOS
2 stops25h 46mMultiple Airlines
Deal found 2/20$343

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 February 20, 2025.

Fly from

Massachusetts

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 3/21

5:10 am-11:34 am

1 stop7h 24m

Chicago Midway

Mon 3/24

8:27 pm-10:33 am

1 stop13h 06m

$152

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/27

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Tue 3/4

6:25 pm-9:40 pm

Nonstop2h 15m

$157

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/30

1:25 pm-9:10 pm

2 stops8h 45m

Chicago Midway

Fri 5/2

9:50 am-4:15 pm

1 stop5h 25m

$222

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/25

5:40 am-8:40 am

1 stop4h 00m

Chicago Midway

Mon 4/28

5:59 pm-11:10 pm

1 stop4h 11m

$237

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/18

3:13 pm-11:50 pm

1 stop9h 37m

Chicago Midway

Mon 4/21

7:05 am-2:25 pm

1 stop6h 20m

$240

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/15

9:05 am-6:20 pm

1 stop10h 15m

Chicago Midway

Tue 4/22

3:02 pm-11:49 pm

1 stop7h 47m

$263

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 3/20

2:30 pm-7:50 pm

2 stops6h 20m

Chicago Midway

Thu 3/27

7:15 am-1:40 pm

1 stop5h 25m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sun 3/23

6:00 am-8:45 am

1 stop3h 45m

Chicago Midway

Sat 3/29

9:25 am-4:15 pm

1 stop5h 50m

$283

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/2

7:07 pm-9:24 am

1 stop15h 17m

$57

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 3/4

5:40 pm-7:30 pm

Nonstop2h 50m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 19 results
1
2

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $57. Users have also found prices from $79 and $99 on Southwest 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 $290, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Boston Logan Intl - Chicago Midway), you can expect to pay $157 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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Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$152FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$147Average$324FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$246FlexibilityNo cancel feeOn-time63%
DeltaCheapest$315Average$435FlexibilityNo cancel feeOn-timeN/A
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