Our data shows that the cheapest route for a return flight from Boston to Chicago cost $151 and was between Boston (BOS) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from Boston (BOS) to Chicago Midway Airport (MDW).

Flights from Boston to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Boston to Chicago. Find the best flights fast, track prices, and...

Find available prices by choosing your travel dates. Prices were available within the past 7 days and start at $47 for one-way flights and $94 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. The cheapest times to …

Find the best deals on flights from Boston Logan International (BOS) to Chicago (CHIA). Compare prices from hundreds of major travel agents and airlines, all in one search.

Cheap Flights from Boston (BOS) to Chicago (CHI) start at $47 for one-way and $106 for round trip. Earn your airline miles on top of our rewards!

Are you searching for American Airlines flights from Boston to Chicago? Find the best selections and fly in style.

Find United Airlines cheap flights from Boston to Chicago. Enjoy a Boston to Chicago modern flight experience in premium cabins with Wi-Fi.

Find the best deals on flights from Boston Logan International (BOS) to Chicago O'Hare International (ORD). Compare prices from hundreds of major travel agents and airlines, all in one search.

Fly one-way from Boston Logan to Chicago (Midway) starting at $79. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Delta flight deals for Boston to Chicago start from as low as $93 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $346. Delta operates 19 flights to Chicago from Boston in an average week.