Cheap flights from Massachusetts to Midway (MDW) from $50
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 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
How far in advance should I book a flight from Massachusetts to Chicago Midway Airport?
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 52 days in advance, which can save you up to 36% on flights from Massachusetts to Chicago Midway Airport compared to booking the week you need them. Waiting 52 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $279. For sooner than that we have options available in the next 3 days from $328.
What is the cheapest month to fly from Massachusetts to Chicago Midway Airport?
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Massachusetts in January are about $273 on average during January, but can be found for as low as $106.
When is the cheapest time to fly from Massachusetts to Chicago Midway Airport (MA - MDW)?
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.
Cheap Frontier flights from Massachusetts to Midway
Explore cheap flight options specifically provided by Frontier for the route between Massachusetts and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Take a look at some of the lowest-priced Frontier flights heading from Massachusetts to Chicago. Deals update often to give you more flight options matching your criteria
Cheap Southwest flights from Massachusetts to Midway
Explore cheap flight options specifically provided by Southwest for the route between Massachusetts and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
To aid your search, here are some of the cheapest Southwest flights we've found from Massachusetts to Chicago. Deals are refreshing constantly so come back soon for more options.
Cheap Massachusetts to Midway flights in May & June 2024
Find cheap flight options from Massachusetts to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Prices were last updated on May 13, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. For more flight deals, be sure to check back very soon.
Massachusetts to Midway 2024 flight deals
Discover exclusive flight deals for travel between Massachusetts and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. For more flight deals, be sure to check back very soon.
Non-stop flights to Midway from Massachusetts
Discover non-stop flight options from Massachusetts to Midway. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Consider booking one of these non-stop flights heading from Massachusetts to Chicago. Those looking to potentially save on 1 or 2-stop flights from Massachusetts to Chicago should utilize the search form at the the top of the page.
Massachusetts to Midway flights leaving soon
Find last-minute flight options from Massachusetts to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Book one of these great deals on flights from Massachusetts to Chicago. It's wise to confirm all flight details are correct before booking.
One-way flights to Midway from Massachusetts
Search for one-way flight options from Massachusetts to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Some of the best available deals we've found on one-way flights from Massachusetts to Chicago. Those seeking round-trip flights from Massachusetts to Chicago should utilize the search form at the the top of the page.
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 2,633,403 searches. Data last updated May 13, 2024.
Fly from
Fly to
Budget
$106 - $404
Route
Depart
Return
Price
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/5
1 stop14h 40m
Chicago Midway
Tue 6/11
1 stop7h 42m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/25
1 stop7h 58m
Chicago Midway
Wed 5/29
1 stop23h 51m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 6/1
1 stop11h 10m
Chicago Midway
Mon 6/3
1 stop8h 27m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 6/1
1 stop11h 10m
Chicago Midway
Mon 6/3
1 stop8h 27m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/29
1 stop6h 50m
Chicago Midway
Thu 5/30
1 stop24h 15m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 6/11
1 stop9h 44m
Chicago Midway
Tue 6/18
1 stop7h 42m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 6/16
Nonstop2h 35m
Chicago Midway
Sat 6/22
Nonstop2h 15m
Albany IntlChicago Midway
ALB - MDW
ALBMDW
Albany Intl
Tue 6/11
1 stop3h 48m
Chicago Midway
Tue 6/18
1 stop4h 35m
Boston Logan IntlChicago Midway
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/19
2 stops12h 52m
Chicago Midway
Fri 6/21
1 stop10h 15m
No data available for this route at this time. Please check back soon.
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 May 13, 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.
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My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
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My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Comfort
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Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Comfort
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Entertainment
Food
Overall
Boarding
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Comfort
Crew
Entertainment
Food
Overall
Boarding
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
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.
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Alternative routes for Massachusetts to MidwaySee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Massachusetts to Midway
Discover the top 4 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 2,633,403 searches. Data last updated May 13, 2024.
Search flights from Massachusetts to Midway by cabin class
Find flights from Massachusetts to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Massachusetts to Midway
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 May 13, 2024.
| 1%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 53%of flight departures | Morning6 am to noon |
| 15%of flight departures | AfternoonNoon to 6 pm |
| 31%of flight departures | Evening6 pm to midnight |
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How does Cheapflights help users find flights from Massachusetts to Midway?
When you search for this flight from Massachusetts to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from Massachusetts to Midway?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Massachusetts to Midway.
Can Cheapflights find flights from Massachusetts to Midway with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Massachusetts to Midway, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Massachusetts to Midway become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!