$63+ Cheap flights from Midway (MDW) to Massachusetts
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Midway to Massachusetts 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 Midway to Massachusetts
Keep the following information in mind while searching for Midway to Massachusetts flight deals. Data was last updated June 12, 2025.
Round-trip from | $125 (Southwest) |
|---|---|
One-way from | $63 (Southwest) |
Popular in | April |
Cheapest in | August |
Average price | $220 |
Good round-trip deal | $137 or less |
Good one-way deal | $68 or less |
Find flight deals from Midway to Massachusetts
Cheapest flights from Midway to MassachusettsExplore the most affordable flight options available from Midway to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Midway to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This Southwest deal was found by Cheapflights users on 6/12. 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.
This Mytrip deal was found by Cheapflights users on 6/11. 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.
This CheapOair deal was found by Cheapflights users on 6/9. 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.
This Southwest deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Mytrip deal was found by Cheapflights users on 6/10. 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.
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Southwest deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/12. 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.
This Delta deal was found by Cheapflights users on 6/11. 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.
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Massachusetts 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 June 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 8/19
6:10 pm-9:35 pm
Nonstop2h 25m
Boston Logan Intl
Thu 8/21
5:15 am-6:45 am
Nonstop2h 30m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 8/1
1:11 pm-9:46 am
1 stop19h 35m
Boston Logan Intl
Sun 8/3
11:31 am-7:13 am
1 stop20h 42m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 8/29
9:17 am-12:08 pm
1 stop25h 51m
Boston Logan Intl
Sun 9/7
9:18 am-7:39 am
1 stop23h 21m
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Thu 8/7
9:45 am-12:50 pm
Nonstop2h 05m
Hartford Bradley Intl
Wed 8/13
2:15 pm-8:25 pm
1 stop7h 10m
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Tue 7/1
1:09 pm-5:42 pm
1 stop3h 33m
Hartford Bradley Intl
Sat 7/5
5:35 am-8:41 am
1 stop4h 06m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 8/1
1:11 pm-11:03 pm
2 stops32h 52m
Boston Logan Intl
Sun 8/3
11:31 am-7:13 am
1 stop20h 42m
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Thu 6/26
9:12 pm-7:48 pm
1 stop21h 36m
Hartford Bradley Intl
Sun 6/29
12:38 pm-11:18 pm
1 stop11h 40m
ChicagoAlbany
MDW - ALB
MDWALB
Chicago Midway
Mon 8/11
6:17 pm-11:21 pm
1 stop4h 04m
Albany Intl
Wed 8/13
6:00 am-8:35 am
1 stop3h 35m
ChicagoAlbany
MDW - ALB
MDWALB
Chicago Midway
Mon 8/11
6:20 pm-9:20 pm
Nonstop2h 00m
Albany Intl
Wed 8/13
12:50 pm-4:25 pm
1 stop4h 35m
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/9
9:25 am-7:44 pm
1 stop9h 19m
Boston Logan Intl
Wed 8/13
9:00 am-6:37 pm
1 stop10h 37m
Best time to book a flight from Midway to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Midway with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Massachusetts
What is the cheapest month to book a flight from Chicago Midway Airport to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $218). Flying from Chicago Midway Airport to Massachusetts in June is currently the most expensive (average of $306). 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 MDW to MA?
Find hourly flight availability from Midway to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Massachusetts as you normally would.
Rainfall in Massachusetts by month
Plan your trip to Massachusetts by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.
Temperature in Massachusetts by month
Plan your trip to Massachusetts by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Massachusetts, 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 30.2 F).
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated June 12, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Southwest, Delta and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Midway to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Midway to Massachusetts
Discover the top 2 airlines that operate flights from Midway to Massachusetts. 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$289 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$297 | FlexibilityNo cancel fee | On-time69% |