
Popular airlines from Logan International Airport (BOS) to Chicago O'Hare Intl. Airport (ORD)
- Spirit Airlines
Spirit Airlines
- JetBlue Airways
JetBlue Airways
- Delta
Delta
- American Airlines
American Airlines
- United
United
- Frontier Airlines
Frontier Airlines
- Southwest Airlines
Southwest Airlines
- Be in the knowGet alerts if flight prices drop or rise*
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Cheap flights from Boston to Chicago (BOS-ORD)
Prices were available within the past 7 days and start at €41 for one-way flights and €80 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€80 Return, found 21 hours ago
€80
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€80 Return, found 21 hours ago
€80
Return
found 21 hours ago

Thu, 8 Jan - Mon, 12 Jan
BOS
Boston
ORD
Chicago
€81 Return, found 22 hours ago
€81
Return
found 22 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€91 Return, found 21 hours ago
€91
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€100 Return, found 21 hours ago
€100
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€102 Return, found 21 hours ago
€102
Return
found 21 hours ago

Wed, 28 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€109 Return, found 21 hours ago
€109
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€110 Return, found 21 hours ago
€110
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€110 Return, found 21 hours ago
€110
Return
found 21 hours ago

Mon, 26 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
€121 Return, found 21 hours ago
€121
Return
found 21 hours ago
Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)
January is typically the cheapest month to fly
From €78 - €140 per traveller.
Origin airport | Logan Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, JetBlue Airways, United |
Return price | €79 |
Distance | 1381 km |
Average flight time | 1 hour 59 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 €41 and roundtrip prices from €80. 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 Belgrade (BOS - BEG)
- Boston to Fort Lauderdale (BOS - FLL)
- Boston to New York (BOS - LGA)
- Boston to Paris (BOS - CDG)
- Boston to New York (BOS - JFK)
- Boston to Dublin (BOS - DUB)
- Boston to Montreal (BOS - YUL)
- Boston to Shannon (BOS - SNN)
- Boston to London (BOS - LHR)
- Boston to Orlando (BOS - MCO)
- Boston to Toronto (BOS - YYZ)
Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
- Knock to Chicago (NOC - ORD)
- New York to Chicago (LGA - ORD)
- Cork to Chicago (ORK - ORD)
- Warsaw to Chicago (WAW - ORD)
- New York to Chicago (JFK - ORD)
- Dublin to Chicago (DUB - ORD)
- Budapest to Chicago (BUD - ORD)
- Shannon to Chicago (SNN - ORD)
- Vienna to Chicago (VIE - ORD)
- Vilnius to Chicago (VNO - ORD)
- London to Chicago (LHR - ORD)
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- Norwood Memorial Airport (OWD)
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