◊Applies to all domestic travel. Book by Dec 31, 2018. ◊ Learn more
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Book Cheap Flights from Boston to Chicago

Looking for flights from Boston (BOS) to Chicago (CHI)? Find affordable air travel deals on CheapOair and save big on air tickets online. The third most populous city in the United States, Chicago is the largest city in the state of Illinois. Chicago impresses with its tall buildings adorning the downtown skyline and other areas with their subtle yet impactful cultural richness. Top Chicago attractions include its set of museums, Shedd Aquarium, Field Museum of Natural History, Adler Planetarium, Art Institute of Chicago, Museum of Photography and others. While in town, you cannot miss out on the rich variety of food options, right from Vietnamese pho, to American Waffles and Swedish almond tarts. To reach Chicago, CHI from Boston, BOS you can choose from the top airlines, Spirit Airlines, American Airlines and US Airways for a comfortable and convenient journey. The average time taken by a flight to cover the distance of 860 miles between the two cities is about 2 hours and 20 minutes.