Weekly, there are 11 flights connecting Boston to Chicago. We've gone through them all to help you find the right flight for you. If you can't find what you're looking for, consider widening your search by looking at flights from a different airport.
Chicago O'hare International Airport (ORD) is the most popular airport in this city for flights to Boston, and the most popular airlines are JetBlue. Both flight prices and accommodation rates fluctuate throughout the year, but searching by month will reveal the cheapest times to fly.
On average, the 1382 km flight to Boston takes 2 hrs 15 mins. If you want a bargain, keep an eye out for flights with JetBlue, as they often have good deals. Or you could broaden your search by looking at flights to other airports in the USA to see if there are any cheaper options.
Once you’ve chosen your flight, why not check out our deals on accommodation and car hire? You’ll find lots of hotels in the USA, including some close to the airport – perfect if you're arriving late or leaving early.
