
Popular airlines from Chicago Midway Airport (MDW) to Logan International Airport (BOS)
- Southwest Airlines
Southwest Airlines
- Delta
Delta
- Frontier Airlines
Frontier Airlines
- Plan, book, fly with confidence
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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.

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$552 Return, found 19 hours ago
NZ$552
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$553 Return, found 19 hours ago
NZ$553
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$555 Return, found 19 hours ago
NZ$555
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$638 Return, found 19 hours ago
NZ$638
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$639 Return, found 19 hours ago
NZ$639
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$669 Return, found 19 hours ago
NZ$669
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$671 Return, found 19 hours ago
NZ$671
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$672 Return, found 19 hours ago
NZ$672
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$696 Return, found 19 hours ago
NZ$696
Return
found 19 hours ago

Mon, 3 Nov. - Tue, 4 Nov.
MDW
Chicago
BOS
Boston
NZ$698 Return, found 19 hours ago
NZ$698
Return
found 19 hours ago
Origin airport | Midway Intl. |
Destination airport | Logan Intl. |
Airlines serving | Delta |
Return price | NZ$551 |
Distance | 1371 km |
Average flight time | 3 hours 19 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 Boston, 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$276 and roundtrip prices from NZ$552. 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 Boston 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 MDW to BOS travel arrangements today and embark on the journey of a lifetime in Boston.
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Top Routes from Chicago
Top Routes to Boston
- Auckland to Boston (AKL - BOS)
- Hong Kong to Boston (HKG - BOS)
- Honolulu to Boston (HNL - BOS)
- Spokane to Boston (GEG - BOS)
- Dunedin to Boston (DUD - BOS)
- Wellington to Boston (WLG - BOS)
- Queenstown to Boston (ZQN - BOS)
- Orlando to Boston (MCO - BOS)
- San Francisco to Boston (SFO - BOS)
- Christchurch to Boston (CHC - BOS)
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Related Carriers
Chicago Airports
Chicago
NZ$227.10
Alternative Routes
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
- Central Illinois Regional Airport (BMI)
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- Toronto to New York (YYZ - NYC)
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