Cheap flights from Boston to Chicago

Flights starting at $84. Choose between Delta Air Lines, JetBlue Airways, or United Airlines to find the best price.

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Travelers usually depart from Logan International, Boston South Station, Boston, MA - Back Bay Station, Boston, MA - LAZ parking lot, or Boston, MA - North Station when they travel from Boston to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago Downtown Greyhound Station. The distance between Boston and Chicago is 1392 km. The most popular airlines for this route are Delta Air Lines, JetBlue Airways, United Airlines, American Airlines, and Frontier Airlines. Boston and Chicago have 401 direct flights per week.

Weekly direct flights

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Fly direct with

American Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

JetBlue Airways on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Delta Air Lines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

United Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Check-in for a flight from Boston to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
JetBlue AirwaysJBUB6YesOpens 24 days before flight
Closes 2 hours before flight
United AirlinesUALUAYesNo
American AirlinesAALAAYesNo
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

How long does it take to travel from Boston to Chicago?
A one-way nonstop (direct) flight between Boston and Chicago takes around 2.9 hours.
What is the flight distance between Boston and Chicago?
The flight distance between Boston and Chicago is 1392 km.
What airlines offer nonstop (direct) flights between Boston and Chicago?
Several carriers operate flights between Boston and Chicago. Airlines offering nonstop (direct) flights include Delta Air Lines, American Airlines, United Airlines, JetBlue Airways.
What are the most popular routes to and from Boston?
Travelers frequently search for route combinations, such as Boston and London, Paris, Orlando, Barcelona, Rome, Madrid, Dublin, Athens, Lisbon, Denver, Prague, Miami, Vienna, Amsterdam, Milan, Munich, Fort Lauderdale, Berlin, Istanbul, Raleigh.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and Phoenix, Las Vegas, Denver, Orlando, San Francisco, Los Angeles, Tampa, Miami, Salt Lake City, New York, Atlanta, London, Sacramento, Minneapolis, Mexico City, Paris, Austin, Washington, D.C., Fort Lauderdale, Fort Myers.
What airports are near Boston?
The main airport in Boston is Logan International. It is also served by Logan International, Bradley International, Rhode Island T. F. Green Int'l Airport, Albany International, Portland International Jetport, Manchester–Boston Regional, Portsmouth International Airport at Pease, Worcester Regional, Barnstable Municipal, Lebanon Municipal.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, General Wayne A. Downing Peoria International, Dane County Regional, Fort Wayne International, Central Illinois Regional, South Bend International, Quad City International, Kalamazoo/Battle Creek International, Decatur.
What buses and trains depart from Boston?
A number of bus and train companies depart from Boston, including Peter Pan Bus, Amtrak train.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between Boston and Chicago?
Yes, it's possible to combine different modes of transport between Boston and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Boston and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
What is Virtual Interlining and how do I use it?
Which airlines fly between Boston and Chicago?
When's the best time to travel between Boston and Chicago?
What flights operate between Boston and Chicago?
How many airports are there near Boston?
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Is it possible to reach Boston by bus or train?
What time do nonstop (direct) flights between Boston and Chicago depart?
What time do nonstop (direct) flights between Boston and Chicago arrive?
What time do flights between Boston and Chicago depart?
What time do flights between Boston and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

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