Cheap Flights from Boston (BOS) to Chicago (ORD)

Pick up great flights from Boston to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Boston to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Boston to Chicago that take around hours.

Find cheap flights from Boston to Chicago

From the great flight deals with prices currently ranging from AU$241 to AU$298, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Boston to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in December.

Reasons to book your flight from Boston to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Boston to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.