Book cheap flights from Chicago to Boston from $5

Last minute flights from Chicago to Boston

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.

Chicago Boston

BEST

DEAL

Tue., 15 Oct. ORD - BOS

Fri., 18 Oct. BOS - ORD

$23

$290 $267

Prime price per passenger

Chicago Boston

BEST

DEAL

Mon., 07 Oct. ORD - BOS

-14 %

$6 $5

Prime price per passenger

Chicago Boston

BEST

DEAL

Thu., 10 Oct. ORD - BOS

Sat., 12 Oct. BOS - ORD

$22

$362 $340

Prime price per passenger

Distance: 1375 kms

Chicago airports

Midway Airport (MDW) How far from city centre: 6 kms

Chicago Nas (NOH) How far from city centre: 35 kms

Dupage County (DPA) How far from city centre: 44 kms

Pal Waukee (PWK) How far from city centre: 35 kms

Greater Rockford (RFD) How far from city centre: 120 kms

O'hare International Airport (ORD) How far from city centre: 22 kms

Boston airports

Tf Green State Airport (PVD) How far from city centre: 76 kms

Logan International Airport (BOS) How far from city centre: 5 kms

Pease Intl Tradeport (PSM) How far from city centre: 80 kms

Boston (BNH) How far from city centre: 0 kms

Lawrence (LWM) How far from city centre: 40 kms

Worcester - James D O'brien Field (ORH) How far from city centre: 67 kms

Get the Best Deals on Flights from Chicago to Boston

Discover the best last-minute airfares and cheap prices from Chicago to Boston 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 Chicago? Adjust your travel dates and explore a wide range of options to Boston. 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 Chicago to Boston 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 Chicago to Boston

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

The total flight time between Chicago and Boston is of around 02:27 hours on average, considering an average distance of 1,394 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 Chicago to Boston at Opodo?

The cheapest price for a flight from Chicago to Boston is $5. 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 Chicago to Boston?

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 Chicago. 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 Chicago and Boston?

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