Cheap flights from Boston to Chicago O'Hare

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Find out what a flight from Boston to Chicago O'Hare might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Boston and Chicago.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Which departure and arrival airports are available?

Between Boston and Chicago, flight options may depend on the combination of airports available.

  • Airports in Boston: Only Boston - Logan is currently in operation.
  • Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Flights from Boston - Logan to Chicago - O'Hare

Plan smarter: flights from Boston to Chicago O'Hare

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Atlanta, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.
Frequently Asked Questions

Frequently asked questions about flights from Boston to Chicago O'Hare.

How much does an airline ticket from Boston to Chicago O'Hare cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Boston to Chicago O'Hare.

How far is Boston from Chicago?

Boston is about 864 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Boston?

Boston has one airport: Boston - Logan.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Boston to Chicago?

The best time to book a flight from Boston to Chicago is 1 month in advance, while the worst time is 7 weeks in advance.

What is the cheapest month to fly from Boston to Chicago?

This information is not available at the moment.

What is the most expensive month to fly from Boston to Chicago?

This information is not available at the moment.

What is the best day of the week to fly from Boston to Chicago?

This information is not available at the moment.