
Popular airlines from Logan International Airport (BOS) to Chicago O'Hare Intl. Airport (ORD)
- JetBlue Airways
JetBlue Airways
- Delta
Delta
- American Airlines
American Airlines
- United
United
- Spirit Airlines
Spirit Airlines
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
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Cheap flights from Boston to Chicago (BOS-ORD)
Prices were available within the past 7 days and start at €51 for one-way flights and €101 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, 19 Nov - Sat, 6 Dec
BOS
Boston
ORD
Chicago
€101 Return, found 17 hours ago
€101
Return
found 17 hours ago

Wed, 19 Nov - Sun, 7 Dec
BOS
Boston
ORD
Chicago
€101 Return, found 17 hours ago
€101
Return
found 17 hours ago

Wed, 12 Nov - Wed, 3 Dec
BOS
Boston
ORD
Chicago
€102 Return, found 17 hours ago
€102
Return
found 17 hours ago

Tue, 4 Nov - Tue, 18 Nov
BOS
Boston
ORD
Chicago
€110 Return, found 17 hours ago
€110
Return
found 17 hours ago

Thu, 30 Oct - Mon, 3 Nov
BOS
Boston
ORD
Chicago
€111 Return, just found
€111
Return
just found

Tue, 28 Oct - Sat, 8 Nov
BOS
Boston
ORD
Chicago
€117 Return, found 17 hours ago
€117
Return
found 17 hours ago

Sat, 8 Nov - Fri, 28 Nov
BOS
Boston
ORD
Chicago
€118 Return, found 17 hours ago
€118
Return
found 17 hours ago

Fri, 27 Feb - Tue, 3 Mar
BOS
Boston
ORD
Chicago
€119 Return, found 2 days ago
€119
Return
found 2 days ago

Tue, 2 Dec - Sat, 13 Dec
BOS
Boston
ORD
Chicago
€123 Return, found 17 hours ago
€123
Return
found 17 hours ago

Mon, 10 Nov - Tue, 11 Nov
BOS
Boston
ORD
Chicago
€132 Return, found 2 days ago
€132
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 €78 - €117 per traveller.
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | Logan Intl. |
---|---|
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, JetBlue Airways, United |
Return price | €101 |
Distance | 1381 km |
Average flight time | 1 hour 52 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 €51 and roundtrip prices from €101. 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 from Boston
- Boston to Newark Liberty Intl. Airport (BOS - EWR)
- Boston to Los Angeles (BOS - LAX)
- Boston to New York (BOS - LGA)
- Boston to Fort Lauderdale (BOS - FLL)
- Boston to Cork (BOS - ORK)
- Boston to Istanbul (BOS - IST)
- Boston to New York (BOS - JFK)
- Boston to Dublin (BOS - DUB)
- Boston to Shannon (BOS - SNN)
- Boston to Nashville (BOS - BNA)
- Boston to Athens (BOS - ATH)
- Boston to Orlando (BOS - MCO)
Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
- New York to Chicago (LGA - ORD)
- Cork to Chicago (ORK - ORD)
- Istanbul to Chicago (IST - ORD)
- Warsaw to Chicago (WAW - ORD)
- New York to Chicago (JFK - ORD)
- Dublin to Chicago (DUB - ORD)
- Shannon to Chicago (SNN - ORD)
- Baltimore to Chicago (BWI - ORD)
- Vilnius to Chicago (VNO - ORD)
- London to Chicago (LHR - ORD)
- Lisbon to Chicago (LIS - ORD)
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