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Midway

$74+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:00 amBOS - MDW
1 stop6h 42mFrontier
Fri 12/137:00 amMDW - BOS
1 stop16h 30mFrontier
Deal found 11/20$124
This Southwest deal was found by Cheapflights users on 11/21. 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.
Wed 12/47:00 amBOS - MDW
Nonstop2h 45mSouthwest
Sun 12/88:00 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 11/21$158
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1210:55 amBDL - MDW
1 stop27h 59mFrontier
Sun 12/155:15 amMDW - BDL
1 stop26h 42mFrontier
Deal found 11/19$258
This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 12/145:40 amALB - MDW
1 stop4h 18mDelta
Tue 12/176:00 amMDW - ALB
1 stop4h 59mDelta
Deal found 11/20$272
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:30 amBDL - MDW
Nonstop2h 30mSouthwest
Wed 1/17:20 amMDW - BDL
1 stop5h 15mSouthwest
Deal found 11/19$277
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 12/255:20 amBDL - MDW
1 stop4h 30mDelta
Mon 1/66:00 amMDW - BDL
1 stop6h 14mDelta
Deal found 11/19$286
This Southwest deal was found by Cheapflights users on 11/21. 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.
Thu 12/1910:40 amALB - MDW
1 stop5h 05mSouthwest
Thu 12/198:20 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 11/21$309
This Delta deal was found by Cheapflights users on 11/20. 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 12/31:03 pmBOS - MDW
1 stop4h 59mDelta
Wed 12/49:31 amMDW - BOS
1 stop5h 19mDelta
Deal found 11/20$316
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Mon 12/231:56 pmBDL - MDW
3 stops26h 07mMultiple Airlines
Mon 1/65:35 pmMDW - BDL
3 stops28h 07mMultiple Airlines
Deal found 11/20$734

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/11

6:00 am-11:42 am

1 stop6h 42m

Chicago Midway

Fri 12/13

7:00 am-12:30 am

1 stop16h 30m

$124

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/4

7:00 am-8:45 am

Nonstop2h 45m

Chicago Midway

Sun 12/8

8:00 am-11:15 am

Nonstop2h 15m

$158

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 1/24

8:19 pm-11:29 pm

2 stops28h 10m

Chicago Midway

Tue 1/28

5:31 pm-3:13 pm

2 stops44h 42m

$243

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 1/7

6:00 am-7:45 am

Nonstop2h 45m

Chicago Midway

Tue 1/7

12:25 pm-3:25 pm

Nonstop2h 00m

$268

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 12/14

5:40 am-8:58 am

1 stop4h 18m

Chicago Midway

Tue 12/17

6:00 am-11:59 am

1 stop4h 59m

$272

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 1/7

7:05 am-1:08 pm

1 stop7h 03m

Chicago Midway

Tue 1/7

6:28 pm-11:08 pm

1 stop3h 40m

$276

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 1/23

5:45 am-7:15 am

Nonstop2h 30m

Chicago Midway

Sat 1/25

5:05 pm-7:55 pm

Nonstop1h 50m

$277

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 12/3

9:05 am-12:49 pm

1 stop4h 44m

Chicago Midway

Mon 12/9

9:30 am-3:50 pm

1 stop5h 20m

$316

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 12/23

6:00 am-8:41 am

2 stops27h 41m

Chicago Midway

Mon 1/6

5:35 pm-10:42 pm

3 stops28h 07m

$573

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/17

10:52 am-5:54 pm

1 stop8h 02m

$74

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 20 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.

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, December is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $159). Flying from Massachusetts to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 November 21, 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 November 21, 2024.
Read reviews from past customers who have flown Frontier, Southwest and Delta 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
5,015 reviews

Food

7.2

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Food

7.2

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Food

7.2

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,015 reviews

Food

7.2

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,015 reviews

Food

7.2

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $74. Users have also found prices from $79 and $138 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 $310, 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 $128 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, December is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $159). Flying from Massachusetts to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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LaGuardia to Midway flights
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San Francisco to Midway flights
Seattle to Midway flights
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Minneapolis to Midway flights
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Dulles Intl to Midway flights
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Reagan-National to Midway flights
Nashville to O'Hare Intl flights
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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$153FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$145Average$234FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$147Average$324FlexibilityNo cancel feeOn-time69%
DeltaCheapest$315Average$440FlexibilityNo cancel feeOn-timeN/A
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