NZ$275 Cheap Flights Chicago to Boston (MDW-BOS)

View NZ$275 flight on Fri, 13 Feb 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Boston

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Cheap Flights from Chicago (MDW) to Boston (BOS)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Flight from Chicago to Boston route information
Origin airport
Midway Intl.
Destination airport
Logan Intl.
Distance
1371 km
Average flight time
3 hours 35 mins

Perfect flights from Chicago to Boston

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Boston. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Midway Intl. to Logan Intl. ticket options cater to your travel preferences, with incredible one-way fares from NZ$275 and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Logan Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Boston.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to Logan Intl. Airport (BOS)?
The lowest price advertised for a round-trip journey between MDW and Logan Intl. Airport is . But you better move fast. This figure is taken from fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago Airport to Logan Intl. Airport (BOS)?
The majority of flights can be cancelled online, but every airline has its own set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Chicago Airport to Logan Intl. 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 Midway Intl. Airport (MDW) to BOS flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Intl. Airport (MDW) to BOS?
The flight distance from Chicago Airport (MDW) to BOS (BOS) is just 1 400 kilometres. You'll be walking down the air bridge and collecting your bags from the carousel in no time at all.
Which airlines fly direct from Midway Airport to Logan Intl. Airport?
Southwest Airlines (WN) will take you from MDW to Logan Intl. Airport (BOS) safely and comfortably. Take your pick of 121 direct flights every month along this route.
Are Midway Airport to BOS flight tickets cheaper when they're purchased at the last minute?
Airline tickets from Midway Airport to Logan Intl. Airport are available up to 12 months before departure on Expedia. And although you may occasionally score a fantastic last-minute deal, it's never a sure thing. Also, booking your flights in advance means you'll have more options — and you can avoid ending up with the dreaded middle seat! We frequently update our fares to bring you the biggest bargains, so check back often for all the latest specials.

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