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Amazing BOS to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $106 round trip and $45 one way. Prices and availability subject to change. Additional terms may apply.

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

FAQs about flights from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)

Are there direct flights from Boston, MA (BOS-Logan Intl.) to Chicago Airport?

For a no-fuss trip between Boston and Chicago, try Southwest Airlines. They advertise direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.).

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Chicago, IL (MDW-Midway Intl.), please visit our Customer Service Portal.

How long is the flight from Boston, MA (BOS-Logan Intl.) to Chicago Airport?

With the flight between Boston and Chicago taking around 3 hours and 20 minutes, you'll have time to get a lot of things done in the air. Make the most of your trip by bringing that novel you always wanted to read, exploring the in-flight entertainment or catching up on some sleep. You'll probably even find you can squeeze in all three before disembarking.

What is the flight distance from Boston, MA (BOS-Logan Intl.) to Chicago Airport?

After taking off from Boston, MA (BOS-Logan Intl.), you'll cover 870 mi before landing at Chicago, IL (MDW-Midway Intl.). That should be enough time to read a couple of chapters of your book and maybe even squeeze in a bit of shut-eye.

What airlines fly from Boston, MA (BOS-Logan Intl.) to Chicago Airport?

Know the dates for your big adventure? Prefer to fly straight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (MDW-Midway Intl.)? With Southwest Airlines offering up to 154 flights each month, you'll be cruising the skies in next to no time.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Tuesdays tend to be the cheapest, according to flight demand on Travelocity in 2019. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Monday, as data shows the start of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2019, flights departing on a Tuesday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2019 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 1-2 weeks prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2019 saved nearly 50% when their return flights consisted of two different airlines or fare types.

*According to flight demand on from January to December 2019. Savings are subject to change based on departure location, date and destination.

Logan Intl. to Midway Intl. Flight FAQ

Traveling FromLogan Intl.
Traveling ToMidway Intl.
Shortest Flight Time0 hours 45 mins
Earliest Departure Time6:35AM CDT
Latest Departure Time3:00PM CDT
Lowest Flight Price$106

Boston to Chicago Carriers and Route Information

Flight path for flights from Logan International Airport to Chicago Midway International Airport.

863.00 miles

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.