Looking for the price of a flight from Chicago to Boston?

There’s no fixed price — fares between Chicago and Boston can vary a lot by day or time.

Select your dates to check current offers.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

Is there more than one airport in Chicago or Boston?

Even short-haul routes can benefit from considering secondary airports. It may open up more flight times or cheaper fares.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in Boston: Boston - Logan is the only airport in operation.

Airports with more daily flights offer more flexibility if plans change or delays occur. If you’re flexible, consider airports near Boston as well.

Adjust your flight filters for Chicago – Boston

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to United States? These cities are popular too: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.