
Popular airlines from Logan International Airport (BOS) to Chicago
- JetBlue Airways
JetBlue Airways
- Delta
Delta
- American Airlines
American Airlines
- United
United
- Spirit Airlines
Spirit Airlines
- Frontier Airlines
Frontier Airlines
- Southwest Airlines
Southwest Airlines
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Cheap Flights from Boston (BOS) to Chicago (CHI)
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 4 Dec - Wed, 10 Dec
BOS
Boston
ORD
Chicago
NZ$227 Return, found 6 days ago
NZ$227
Return
found 6 days ago

Tue, 17 Mar - Tue, 31 Mar
BOS
Boston
ORD
Chicago
NZ$243 Return, found 4 days ago
NZ$243
Return
found 4 days ago

Wed, 27 May - Tue, 16 June
BOS
Boston
ORD
Chicago
NZ$244 Return, found 4 days ago
NZ$244
Return
found 4 days ago

Thu, 4 Dec - Wed, 10 Dec
BOS
Boston
ORD
Chicago
NZ$271 Return, found 6 days ago
NZ$271
Return
found 6 days ago

Tue, 17 Mar - Sat, 4 Apr
BOS
Boston
ORD
Chicago
NZ$278 Return, found 4 days ago
NZ$278
Return
found 4 days ago

Wed, 27 May - Wed, 17 June
BOS
Boston
ORD
Chicago
NZ$280 Return, found 4 days ago
NZ$280
Return
found 4 days ago

Thu, 4 Dec - Wed, 10 Dec
BOS
Boston
ORD
Chicago
NZ$298 Return, found 6 days ago
NZ$298
Return
found 6 days ago

Fri, 20 Mar - Sat, 4 Apr
BOS
Boston
ORD
Chicago
NZ$314 Return, found 4 days ago
NZ$314
Return
found 4 days ago

Thu, 4 Dec - Wed, 10 Dec
BOS
Boston
ORD
Chicago
NZ$352 Return, found 6 days ago
NZ$352
Return
found 6 days ago

Sun, 28 Dec - Sun, 4 Jan
BOS
Boston
ORD
Chicago
NZ$1,846 Return, found 3 days ago
NZ$1,846
Return
found 3 days ago
Origin airport | Logan Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Return price | NZ$227 |
Distance | 1381 km |
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 CHI-All Airports ticket options cater to your travel preferences, with incredible one-way fares from NZ$105 and roundtrip prices from NZ$227. 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 CHI-All Airports 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.
Explore a world of travel with Expedia
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Chicago Flight Deals
Madison
NZ$448.80
Chicago
NZ$560.80
Expedia's Latest Trends
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