Select airline tickets from Boston to Chicago from 68.38 USD

Cheap flight tickets from Boston to Chicago

Want to buy the cheapest flight from Boston to Chicago at the best price? We compare prices for both direct Boston – Chicago flights and flights with layovers across 750 airlines and travel agencies. Why waste your time searching manually when you can easily access discounts, deals, and low-cost airline sales online? With our complete Boston – Chicago flight schedule, you’ll quickly find the best option — just check flight days and ticket availability for your selected date.

To book or buy a ticket online, all you need to do is select the type of flight, number of passengers, class, and departure and return dates. Proceed to payment — and you’re all set. You'll receive an email with your booking details.

Boston – Chicago flight ticket prices

How much is a plane ticket to Chicago from Boston, and how can you get it cheaper? We’ve got a few tips, based on our best-price calendar for this route:

1) Prices vary depending on the departure month. We recommend booking first or business class tickets in advance. Don’t delay with economy either — 2 to 4 months ahead is best.
2) The cheapest BOS – CHI flights are usually available on Wednesdays and Thursdays. Weekend prices are typically higher.
3) Round-trip tickets are often cheaper than buying two one-way flights separately.

Useful info before booking your trip from Boston to Chicago

With our service, you can find out:

• Flight distance and duration from Boston to Chicago
• Which airlines operate direct flights on the Boston – Chicago route
• Which airlines offer the cheapest tickets from Boston to Chicago
• Which airports you can fly from in Boston and arrive at in Chicago