Cheap flights from Boston (BOS) to Chicago (CHI)

Leaving Boston for Chicago takes you to the cultural center of the Midwest and the Great Lakes region. Chicago has many places to explore, such as Grant Park that borders Lake Michigan, the Museum Campus which includes Soldier Field, the Field Museum and the Shedd Aquarium. You can also visit the Addler Planetarium and the downtown Loop area, which features iconic buildings such as the Willis Tower. In addition to the sports, arts and culture, Chicago is known as a major shopping destination for guests, with boutiques and department stores lining the Magnificent Mile of Michigan Avenue.

Key Facts

Take your rental car along the Edens Expressway to Woodfield Mall for a day of indoor shopping. The Edens will also take you to the north suburbs including Evanston, where you can watch a play on the Northwestern University campus, or attend a Northwestern Wildcats football game at Ryan Field.

Hints and Tips

Your flight from Logan International Airport (BOS) to O'Hare International Airport (ORD) should take three hours. Once your plane lands in Chicago, you can pick up your rental car and head over to the Navy Pier. Once there you can explore Naval history, ride the Ferris wheel and enjoy a Chicago-style hot dog and fries. You can continue your exploration of the city by taking Lake Shore Drive over to Lincoln Park and going for a jog.