Cheap flights from Boston, MA to Chicago, IL

Flights starting at £41. Choose between Delta Air Lines, Frontier Airlines, or American Airlines to find the best price.

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Round trips

Boston BOSChicago ORD

United Airlines

£144

Updated:

One-way trips

Boston BOSChicago ORD

United Airlines

£72

Updated:

1392 km
Distance
Duration
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Travelers usually depart from Logan International, Boston South Station, Boston, MA - Back Bay Station, 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, Frontier Airlines, American Airlines, JetBlue Airways, and Spirit Airlines. Boston and Chicago have 401 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights17171718171317
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
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
American AirlinesAALAAYesNo
JetBlue AirwaysJBUB6YesOpens 24 days before flight
Closes 2 hours before flight
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight

United States COVID-19 travel restrictions

Your trip summary

Most travelers from Boston, BOS can enter Chicago, ORD.

Departure

Additional information
  • Masks are recommended in certain settings

Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.

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 3.0 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, JetBlue Airways, United Airlines.
What are the most popular routes to and from Boston?
Travelers frequently search for route combinations, such as Boston and London, Dublin, Edinburgh, Athens, Manchester, Vilnius, New Orleans, Orlando, Washington, D.C., Paris, New York, San Francisco, Atlanta, Raleigh, Rome, Vienna, Miami, Glasgow, Las Vegas, Buffalo.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and London, Dublin, Manchester, Toronto, Athens, Orlando, San Francisco, Hyderabad, Vilnius, New York, Las Vegas, Edinburgh, Denver, Bangkok, Minneapolis, Riga, Glasgow, Austin, San Juan, Edmonton.
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, Augusta State, Worcester Regional, Portsmouth International Airport at Pease, 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, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, South Bend International, Quad City International, Central Illinois Regional, Muskegon County, University of Illinois Willard.
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?
Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.
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?
How many airports are there near Chicago?
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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