
Popular airlines from Chicago Midway Airport (MDW) to Logan International Airport (BOS)
- Southwest Airlines
Southwest Airlines
- Delta
Delta
- Frontier Airlines
Frontier Airlines
- Be in the knowGet alerts if flight prices drop or rise*
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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.

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$649 Return, found 1 day ago
NZ$649
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$774 Return, found 1 day ago
NZ$774
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$880 Return, found 1 day ago
NZ$880
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,065 Return, found 1 day ago
NZ$1,065
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,190 Return, found 1 day ago
NZ$1,190
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,226 Return, found 1 day ago
NZ$1,226
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,349 Return, found 1 day ago
NZ$1,349
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,420 Return, found 1 day ago
NZ$1,420
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,481 Return, found 1 day ago
NZ$1,481
Return
found 1 day ago

Sun, 28 Dec - Sun, 4 Jan
MDW
Chicago
BOS
Boston
NZ$1,642 Return, found 1 day ago
NZ$1,642
Return
found 1 day ago
Travel information
Origin airport | Midway Intl. |
|---|---|
Destination airport | Logan Intl. |
Airlines serving | Delta |
Return price | NZ$649 |
Distance | 1371 km |
Average flight time | 3 hours 16 mins |
Book with confidence
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$281 and roundtrip prices from NZ$649. 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.
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Top Routes to Boston
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Chicago Airports
Chicago
NZ$208.20
Alternative Routes
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*Available to Expedia members.