
Popular airlines from Chicago O'Hare International Airport (ORD) to Logan International Airport (BOS)
- Spirit Airlines
Spirit Airlines
- JetBlue Airways
JetBlue Airways
- American Airlines
American Airlines
- Delta
Delta
- United
United
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
- Plan, book, fly with confidence
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Cheap Flights from Chicago (ORD) to Boston (BOS)
Prices were available within the past 7 days and start at ฿2,245 for one-way flights and ฿4,470 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿4,470 Return, found 1 day ago
฿4,470
Return
found 1 day ago

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿5,610 Return, found 1 day ago
฿5,610
Return
found 1 day ago

Sun, 21 Sep - Tue, 23 Sep
ORD
Chicago
BOS
Boston
฿5,630 Return, found 3 days ago
฿5,630
Return
found 3 days ago

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿5,795 Return, found 1 day ago
฿5,795
Return
found 1 day ago

Sun, 21 Sep - Wed, 24 Sep
ORD
Chicago
BOS
Boston
฿5,890 Return, found 3 days ago
฿5,890
Return
found 3 days ago

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿6,125 Return, found 1 day ago
฿6,125
Return
found 1 day ago

Thu, 21 Aug - Mon, 25 Aug
ORD
Chicago
BOS
Boston
฿6,190 Return, found 2 days ago
฿6,190
Return
found 2 days ago

Thu, 21 Aug - Mon, 25 Aug
ORD
Chicago
BOS
Boston
฿6,710 Return, found 2 days ago
฿6,710
Return
found 2 days ago

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿6,740 Return, found 1 day ago
฿6,740
Return
found 1 day ago

Fri, 15 Aug - Tue, 19 Aug
ORD
Chicago
BOS
Boston
฿6,740 Return, found 1 day ago
฿6,740
Return
found 1 day ago
Find the cheapest month to fly from Chicago (ORD) to Boston (BOS)
September is typically the cheapest month to fly
From ฿1,815 - ฿3,792 per traveller.
Graph displaying average flight prices per month
Origin airport | O'Hare Intl. |
Destination airport | Logan Intl. |
Return price | ฿4,470 |
Distance | 1381 km |
Average flight time | 3 hours 24 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 O'Hare Intl. to Logan Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿2,245 and roundtrip prices from ฿4,470. 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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