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

There’s no fixed price — fares between Boston and Chicago 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.

Best airport options between Boston and Chicago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Boston: Boston - Logan is the only operating airport.
• Airports in Chicago: In Chicago, 3 airports are available - Midway, O'Hare, Rockford.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Explore flights from Boston to Chicago O'Hare your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by specific travel agency.

Other popular destinations

Also interested in United States? Check out: Boston, Los Angeles, Miami, New York City, Orlando.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.