
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 to Boston (MDW-BOS)
Prices were available within the past 7 days and start at €60 for one-way flights and €197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, 17 Aug - Thu, 21 Aug
MDW
Chicago
BOS
Boston
€197 Return, found 1 day ago
€197
Return
found 1 day ago

Sat, 16 Aug - Sat, 23 Aug
MDW
Chicago
BOS
Boston
€275 Return, found 11 hours ago
€275
Return
found 11 hours ago

Thu, 4 Sep - Sun, 7 Sep
MDW
Chicago
BOS
Boston
€278 Return, found 4 days ago
€278
Return
found 4 days ago

Thu, 4 Sep - Sun, 7 Sep
MDW
Chicago
BOS
Boston
€283 Return, found 2 days ago
€283
Return
found 2 days ago

Tue, 9 Sep - Wed, 10 Sep
MDW
Chicago
BOS
Boston
€284 Return, found 6 days ago
€284
Return
found 6 days ago

Tue, 9 Sep - Wed, 10 Sep
MDW
Chicago
BOS
Boston
€285 Return, found 6 days ago
€285
Return
found 6 days ago

Thu, 4 Sep - Sun, 7 Sep
MDW
Chicago
BOS
Boston
€286 Return, found 6 days ago
€286
Return
found 6 days ago

Tue, 19 Aug - Fri, 22 Aug
MDW
Chicago
BOS
Boston
€291 Return, found 1 day ago
€291
Return
found 1 day ago

Tue, 19 Aug - Fri, 22 Aug
MDW
Chicago
BOS
Boston
€308 Return, found 1 day ago
€308
Return
found 1 day ago

Fri, 15 Aug - Sun, 17 Aug
MDW
Chicago
BOS
Boston
€309 Return, found 12 hours ago
€309
Return
found 12 hours ago
Find the cheapest month to fly from Chicago (MDW) to Boston (BOS)
September is typically the cheapest month to fly
From €82 - €298 per traveller.
Graph displaying average flight prices per month
Origin airport | Midway Intl. |
Destination airport | Logan Intl. |
Airlines serving | Delta |
Return price | €197 |
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 €60 and roundtrip prices from €197. 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 to Boston
- Newark Liberty Intl. Airport to Boston (EWR - BOS)
- Los Angeles to Boston (LAX - BOS)
- Washington to Boston (DCA - BOS)
- Belgrade to Boston (BEG - BOS)
- New York to Boston (LGA - BOS)
- Cork to Boston (ORK - BOS)
- Charlotte to Boston (CLT - BOS)
- Tirana to Boston (TIA - BOS)
- Washington to Boston (IAD - BOS)
- New York to Boston (JFK - BOS)
- Dublin to Boston (DUB - BOS)
- Shannon to Boston (SNN - BOS)
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