
Popular airlines from Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD)
- JetBlue Airways
JetBlue Airways
- Spirit Airlines
Spirit Airlines
- United
United
- Delta
Delta
- American Airlines
American Airlines
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
- Plan, book, fly with confidence
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Cheap Flights from Boston (BOS) to Chicago (ORD)
Prices were available within the past 7 days and start at ฿1,935 for one-way flights and ฿3,870 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿3,870 Return, found 12 hours ago
฿3,870
Return
found 12 hours ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,195 Return, found 2 days ago
฿4,195
Return
found 2 days ago

Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿4,200 Return, found 12 hours ago
฿4,200
Return
found 12 hours ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,520 Return, found 2 days ago
฿4,520
Return
found 2 days ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,525 Return, found 2 days ago
฿4,525
Return
found 2 days ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,595 Return, found 2 days ago
฿4,595
Return
found 2 days ago

Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿4,730 Return, found 12 hours ago
฿4,730
Return
found 12 hours ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,920 Return, found 2 days ago
฿4,920
Return
found 2 days ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿4,925 Return, found 2 days ago
฿4,925
Return
found 2 days ago

Thu, 4 Sep - Mon, 8 Sep
BOS
Boston
ORD
Chicago
฿5,455 Return, found 2 days ago
฿5,455
Return
found 2 days ago
Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)
September is typically the cheapest month to fly
From ฿1,811 - ฿3,675 per traveller.
Graph displaying average flight prices per month
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, United |
Return price | ฿3,870 |
Distance | 1381 km |
Average flight time | 1 hour 51 mins |
Perfect flights from Boston to Chicago
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Boston to Chicago. 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 Logan Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿1,935 and roundtrip prices from ฿3,870. 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 O'Hare 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 Chicago.
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Top Routes to Chicago
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