How much is a flight from Boston to Chicago?

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

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Boston - Chicago route.

Exploring all airports near Boston and Chicago

Checking all the airports available in the area can give you more departure and arrival options for your trip.

• Airports in Boston: Boston - Logan is currently the only one operating.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Find the best flight from Boston to Chicago

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from the best airlines and travel agencies.

Other popular destinations

Searching for flights to United States? Travelers also looked at: Atlanta, Los Angeles, Miami, New York City, Orlando.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Boston – Chicago flights.