
Popular airlines from Logan International Airport (BOS) to Chicago
- JetBlue Airways
JetBlue Airways
- Delta
Delta
- Spirit Airlines
Spirit Airlines
- American Airlines
American Airlines
- United
United
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier 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.

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
ORD
Chicago
NZ$238 Return, found 1 day ago
NZ$238
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
ORD
Chicago
NZ$238 Return, found 1 day ago
NZ$238
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
ORD
Chicago
NZ$273 Return, found 1 day ago
NZ$273
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
ORD
Chicago
NZ$341 Return, found 1 day ago
NZ$341
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
MDW
Chicago
NZ$548 Return, found 1 day ago
NZ$548
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
MDW
Chicago
NZ$634 Return, found 1 day ago
NZ$634
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
MDW
Chicago
NZ$775 Return, found 1 day ago
NZ$775
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
MDW
Chicago
NZ$903 Return, found 1 day ago
NZ$903
Return
found 1 day ago

Sat, 13 Dec - Tue, 13 Jan
BOS
Boston
MDW
Chicago
NZ$1,058 Return, found 1 day ago
NZ$1,058
Return
found 1 day ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,076 Return, found 6 days ago
NZ$1,076
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,092 Return, found 6 days ago
NZ$1,092
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,187 Return, found 6 days ago
NZ$1,187
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,213 Return, found 6 days ago
NZ$1,213
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,230 Return, found 6 days ago
NZ$1,230
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,247 Return, found 6 days ago
NZ$1,247
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,299 Return, found 6 days ago
NZ$1,299
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,300 Return, found 6 days ago
NZ$1,300
Return
found 6 days ago

Thu, 9 Oct - Mon, 13 Oct
BOS
Boston
ORD
Chicago
NZ$1,334 Return, found 6 days ago
NZ$1,334
Return
found 6 days ago
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Return price | NZ$238 |
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$359 and roundtrip prices from NZ$238. 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.
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Top Routes from Boston
- Boston to Newark Liberty Intl. Airport (BOS - EWR)
- Boston to Chicago (BOS - MDW)
- Boston to Auckland (BOS - AKL)
- Boston to Los Angeles (BOS - LAX)
- Boston to Honolulu (BOS - HNL)
- Boston to New York (BOS - LGA)
- Boston to Charlotte (BOS - CLT)
- Boston to New York (BOS - JFK)
- Boston to Wellington (BOS - WLG)
- Boston to Dallas (BOS - DFW)
- Boston to Beijing (BOS - PEK)
- Boston to London (BOS - LHR)
Top Routes from Boston
Top Flight Destinations
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- Flights to Seattle
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Chicago Flight Deals
Chicago
NZ$547.80
Expedia's Latest Trends
Flights
- Boston to Auckland (BOS - AKL)
- Toronto to New York (YYZ - NYC)
- Auckland to Dallas (AKL - DFW)
- Seattle to Auckland (SEA - AKL)
- Houston to Orlando (HOU - MCO)
- Auckland to Las Vegas (AKL - LAS)
- New York to Las Vegas (NYC - LAS)
- Boston to New York (BOS - JFK)
- Auckland to New York (AKL - NYC)
- Las Vegas to New York (LAS - JFK)
- Auckland to Anchorage (AKL - ANC)
- Honolulu to Las Vegas (HNL - LAS)
- Las Vegas to Auckland (LAS - AKL)
- Auckland to Seattle (AKL - SEA)
- Auckland to Philadelphia (AKL - PHL)
- London to New York (LON - NYC)
- Auckland to San Diego (AKL - SAN)
- New York to Los Angeles (NYC - LAX)
- San Francisco to Las Vegas (SFO - LAS)
- Houston to New Orleans (HOU - MSY)
- Las Vegas to San Francisco (LAS - SFO)
- Auckland to Cincinnati (AKL - CVG)
- Dallas to Auckland (DFW - AKL)
- Miami to New York (MIA - NYC)
- Los Angeles to San Diego (LAX - SAN)
- Auckland to Boston (AKL - BOS)
- Las Vegas to Los Angeles (LAS - LAX)
- Vancouver to Anchorage (YVR - ANC)
- Los Angeles to Las Vegas (LAX - LAS)
- Los Angeles to Seattle (LAX - SEA)
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