Book cheap flights from Boston to Chicago from $75

Last minute flights from Boston to Chicago

Book now before it's too late

Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Boston Chicago

BEST

DEAL

Wed., 01 Jan. BOS - MDW

Thu., 09 Jan. MDW - BOS

-10 %

$291 $261

Prime price per passenger

Boston Chicago

BEST

DEAL

Tue., 28 Jan. BOS - ORD

-10 %

$83 $75

Prime price per passenger

Boston Chicago

BEST

DEAL

Wed., 08 Jan. BOS - ORD

Wed., 15 Jan. ORD - BOS

-14 %

$182 $156

Prime price per passenger

Boston Chicago

BEST

DEAL

Mon., 13 Jan. BOS - ORD

Wed., 15 Jan. ORD - BOS

-12 %

$228 $200

Prime price per passenger

Distance: 1375 kms

Boston airports

Chicago airports

Get the Best Deals on Flights from Boston to Chicago

Discover the best last-minute airfares and cheap prices from Boston to Chicago with Opodo Australia. Avoid overspending on flight tickets and start planning your perfect getaway. Opodo offers a hassle-free booking experience, providing access to top airline carriers and the most competitive prices.

Find the best flights that fit your needs

When do you want to depart from Boston? Adjust your travel dates and explore a wide range of options to Chicago. With Opodo, you can find the perfect flight from our extensive selection, ensuring a seamless and enjoyable trip. Compare prices, flight durations, and amenities to choose the best option that suits your needs.

Book all in one place

But wait, there's more! Enhance your travel experience by booking a hotel and renting a car along with your flight. It's easier and often cheaper to book everything together. Choose the best offer from Boston to Chicago and get ready for an incredible journey. Enjoy your holiday, and remember to fasten your seatbelt. We’re ready for takeoff!

Frequently asked questions about flights from Boston to Chicago

How long does the flight take to go from Boston to Chicago?

The total flight time between Boston and Chicago is of around 02:54 hours on average, considering an average distance of 1,391 km, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).

How can I find cheap flights from Boston to Chicago at Opodo?

The cheapest price for a flight from Boston to Chicago is $75. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

Is it possible to purchase a flexible ticket for my flight from Boston to Chicago?

At Opodo we want to make sure that your travel plans are not affected by any cancelation as well as any possible restrictions United States may apply when travelling from Boston. Is your flight cancelled? We've got your back! With our flexible ticket guarantee you can decide if you want to book another flight - free of rebooking fee - or get a full refund!

Which airports have flights between Boston and Chicago?

The main airport route flying between Boston and Chicago is: Logan International Airport (BOS) to O hare International Airport (ORD). This route is covered by the following airline(s): United Airlines. American Airlines. Spirit Airlines.