HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$55+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
janv. 27 — févr. 31
lun. 1/27
lun. 2/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 janvier 22, 2025.

Round-trip from

$150
(FlightHub)

One-way from

$55
(Frontier)

Good round-trip deal

$224 or less

Good one-way deal

$177 or less
From Massachusetts to Chicago Midway
Search Deals
One-way flight from Massachusetts to Chicago Midway
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago Midway.
Search Deals

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 janvier 22, 2025.

This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/1512:59 pmBOS - MDW
1 stop8h 34mFrontier
dim. 5/184:00 pmMDW - BOS
1 stop16h 34mFrontier
Deal found 1/21$149
This Southwest deal was found by Cheapflights users on 1/21. 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.
jeu. 2/136:50 amBOS - MDW
Nonstop2h 55mSouthwest
dim. 2/168:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/21$157
This Delta deal was found by Cheapflights users on 1/21. 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.
jeu. 2/137:00 amBDL - MDW
1 stop7h 05mDelta
lun. 2/176:28 pmMDW - BDL
1 stop3h 35mDelta
Deal found 1/21$277
This Frontier deal was found by Cheapflights users on 1/20. 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.
ven. 3/72:59 pmBDL - MDW
1 stop9h 59mFrontier
lun. 3/246:20 amMDW - BDL
1 stop6h 39mFrontier
Deal found 1/20$280
This Southwest deal was found by Cheapflights users on 1/22. 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.
mar. 5/67:55 amBDL - MDW
2 stops7h 40mSouthwest
mar. 5/138:15 amMDW - BDL
1 stop5h 45mSouthwest
Deal found 1/22$282
This Delta deal was found by Cheapflights users on 1/22. 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.
jeu. 3/65:50 amALB - MDW
1 stop4h 01mDelta
lun. 3/106:42 pmMDW - ALB
1 stop3h 36mDelta
Deal found 1/22$289
This Southwest deal was found by Cheapflights users on 1/22. 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.
dim. 3/22:50 pmALB - MDW
2 stops7h 45mSouthwest
mar. 3/41:45 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 1/22$294
This Delta deal was found by Cheapflights users on 1/21. 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.
ven. 2/145:20 amBOS - MDW
1 stop4h 31mDelta
mar. 2/182:08 pmMDW - BOS
1 stop8h 29mDelta
Deal found 1/21$300
This eDestinos deal was found by Cheapflights users on 1/21. 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.
lun. 1/278:00 amBDL - MDW
2 stops17h 17mMultiple Airlines
mar. 1/2812:44 pmMDW - BDL
2 stops25h 29mMultiple Airlines
Deal found 1/21$673

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 janvier 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jeu. 5/15

12:59 pm-8:33 pm

1 stop8h 34m

Chicago Midway

dim. 5/18

4:00 pm-9:34 am

1 stop16h 34m

$149

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jeu. 2/13

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

dim. 2/16

8:20 pm-11:35 pm

Nonstop2h 15m

$157

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jeu. 2/13

7:00 am-1:05 pm

1 stop7h 05m

Chicago Midway

lun. 2/17

6:28 pm-11:03 pm

1 stop3h 35m

$277

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jeu. 2/20

1:30 pm-10:00 pm

1 stop9h 30m

Chicago Midway

jeu. 2/27

12:05 pm-7:15 pm

2 stops6h 10m

$282

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

ven. 2/14

2:27 pm-11:58 pm

1 stop10h 31m

Chicago Midway

mar. 2/18

8:30 am-11:07 am

1 stop25h 37m

$284

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

jeu. 3/6

5:50 am-8:51 am

1 stop4h 01m

Chicago Midway

lun. 3/10

6:42 pm-11:18 pm

1 stop3h 36m

$289

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

dim. 3/2

2:50 pm-9:35 pm

2 stops7h 45m

Chicago Midway

mar. 3/4

1:45 pm-4:35 pm

Nonstop1h 50m

$294

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ven. 2/14

5:20 am-8:51 am

1 stop4h 31m

Chicago Midway

mar. 2/18

2:08 pm-11:37 pm

1 stop8h 29m

$300

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jeu. 2/27

11:40 am-6:20 pm

1 stop7h 40m

$55

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jeu. 2/13

6:50 am-8:45 am

Nonstop2h 55m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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 janvier 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 janvier 22, 2025.
Read reviews from past customers who have flown Frontier, Delta and Southwest 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
4,654 reviews

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Overall

8.1

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
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Overall

8.1

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
8,514 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Overall

8.1

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
801 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Overall

8.1

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
3,442 reviews
Southwest
8.1
Very good
4,654 reviews

Crew

8.7

Entertainment

7.7

Food

7.2

Comfort

8.1

Boarding

8.2

Overall

8.1

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 Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $79 and $135 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 $338, 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.

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Los Angeles to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Newark to Midway flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Los Angeles to Midway flights
Atlanta to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Baltimore to Midway flights
Fort Lauderdale to O'Hare Intl flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
Minneapolis to Midway flights
Austin to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
Tampa to O'Hare Intl flights
Ontario to O'Hare Intl flights
Denver to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Reagan-National to Midway flights
San Jose to O'Hare Intl flights
Love Field to O'Hare Intl flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
Hartford to O'Hare Intl flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Nashville to O'Hare Intl flights
Hobby to Midway 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 janvier 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$150FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$147Average$324FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$149Average$239FlexibilityNo cancel feeOn-time63%
DeltaCheapest$315Average$437FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.