Tips for finding the best connections from Chicago to Boston

A weekday or weekend flight – you decide when you want to fly from Chicago to Boston. A quick search through the database indicates that ticket prices start at a reasonable $45. Flights on Tuesdays can cost up to 41 % less than flights on any other day of the week.

JetBlue Airways, American Airlines, United Airlines and US Airways are especially popular

JetBlue Airways is chosen 70 % of the time by idealo customers, making it the most frequently used airline for this route. Find a direct flight to Boston every day with either American Airlines, JetBlue Airways, Spirit Airlines or United Airlines. With prices starting from $45 per ticket for a direct flight, this is the most affordable offer in our database. Prices for connections with stopovers start at $75, but if you're more interested in direct flights you can find tickets for only $45. Only 25 % of idealo users prefer stopover connections and 61 % prefer direct flights. The most popular stopover flights are those with stops in New York or Philadelphia. With a flight duration of 4 hours and 10 minutes, flights that stop in Philadelphia are the fastest connections with a stopover. This connection is only 2 hours longer than a direct flight. Whether you prefer a direct or a non-stop flight, here at idealo we can find the best deal for you.