An airplane exhibit labeled "Concourse A" in an airport terminal.

NZ$282 Cheap Flights Boston to Chicago (BOS-MDW)

Flight 1

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Cheap Flights from Boston to Chicago (BOS-MDW)

Prices were available within the past 7 days and start at NZ$282 for one-way flights and NZ$563 for return, for the period specified. Prices and availability are subject to change.

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BOS to MDW Flights

Ready to have the time of your life? When you use Expedia.co.nz to book cheap flights from Boston to Chicago, you can experience all of the attractions this city is famous for, or escape the crowds and explore the outskirts on your own. Our amazing deals on airfare help you save big on tickets, so you can spend more of your hard-earned money enjoying local entertainment options. Even if you seek to score a seat on one of the last-minute BOS to MDW flights, you’ll still save a bundle when compared to the competition.

See for yourself how simple it is to book the holiday of your dreams to Chicago by using our helpful search engine today. We have the largest inventory of flights on the internet, and our intuitive tools make it easy to find affordable airfare at any time of year.

Prefer to fly with a particular airline? Our extensive network of travel partners ensures that you can travel with whichever carrier you prefer. So if you’ve been searching for cheap flights to Chicago from Boston, Expedia.co.nz has exactly what you’re looking for. As the world’s leader in travel, we’re committed to helping you get the best rates around.

Frequently Asked Questions

How much is a flight from Logan Intl. Airport to Midway Intl. Airport (MDW)?

Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from Logan Intl. Airport (BOS) to MDW start from NZ$563. Make your booking today to score the best price for your journey. Prices and availability are subject to change. Additional terms apply.

Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to MDW?

The majority of flights can be cancelled online, but whether you are charged a fee depends on your airline. If you do need to cancel your getaway, follow the easy instructions in the Customer Service Portal.

How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago Airport that have flexible change policies?

Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for BOS to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.

How far is the flight from Logan Intl. Airport (BOS) to Chicago Airport?

You can forget about a movie marathon on this flight — it's only 1 400 kilometres from Boston to Chicago. Find your seat, get comfortable and you'll be there before you know it.

Which airlines fly direct from Logan Intl. Airport to Chicago Airport?

If you're looking to fly directly from Logan Intl. Airport to MDW, Southwest Airlines (WN) is an excellent choice. It operates 121 flights every month between Boston and Chicago.

Are Logan Intl. Airport (BOS) to MDW flight tickets cheaper when they're purchased at the last minute?

Late planners can sometimes pick up a bargain, with some super cheap airfares from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) showing up a few weeks prior to the departure date. If you'd rather plan ahead, Expedia compares and updates all the best flight deals continually — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices that far in advance.

Travel information

Origin airport
Logan International Airport
Destination airport
Chicago Midway Airport
Distance
1,379 km away
Airlines serving
Delta, Southwest Airlines, Frontier Airlines
Popular airline
Delta
Return price
NZ$563
Average flight time
2 hours 45 mins
*Available to Expedia members.