Find Cheap Flights from Boston (BOS) to Chicago (CHI)

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Book Cheap Flights from Boston to Chicago

Fly to the Windy City for less

Things to know before you book your flights from Boston to Chicago

A guide to Chicago

Chicago is an international center of technology, industry, and finance. The metropolitan city is a cultural hub with a 24*7 nightlife, extensive shopping venues, and a thriving culinary scene. Chicago is home to many state-of-the-art museums, live performance venues, and theater companies. The city is home to a diverse local populace with multiple ethnic neighborhoods, namely, Little Italy, Little Seoul, Puerto Rican Paseo Boricua, Chinatown, and Little Vietnam. Food lovers must not forget to grab a bite as they explore these vibrant neighborhoods and get a taste of the world, in cosmopolitan Chicago.

Chicago hosts several annual festivals around the year. Few of the major festivals held in Chicago are Chicago Wine Fest (April), 57th Street Art Fair (June), Chicago Blues Festival (June), Taste of Chicago (July), Chicago Food Truck Festival (July), Chicago Craft Beer Festival (July), Lollapalooza Chicago (August), Chicago Hot Dog Fest (August), Illinois State Fair (August), Chicago Jazz Festival (September), Chicago World Music Festival (September), and Windy City Wine Festival (September). Visitors can book Boston to Chicago flight tickets keeping in mind such prominent events.

Major attractions in Chicago

  • The Art Institute of Chicago
  • Millennium Park
  • Navy Pier
  • 360 Chicago
  • Chicago Riverwalk and Lakefront Trail
  • Willis Tower SkyDeck
  • Lincoln Park
  • Museum of Science and History
  • Michigan Avenue and the Magnificent Mile
  • Field Museum of Natural History

When to Visit Chicago

Weather-wise, the best time to visit Chicago is between September and October and from April through May. However, summer is the peak tourist season when the city is flooded with tourists. It is advisable to book your flights from Boston to Chicago in advance.

Share your Travel experience:

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Chicago Travelers' Reviews

Great music destination

Amazing music! Loved Frenchman st the most. Wonderful food wherever you go - Natalie  Dec 05, 2021

Thanksgiving visit

Visited family in Delray is always a nice place to visit much diverisity of activity. For the art and nightlife lover Delray is the place to go. Very congested on main drag. - valarie  Dec 03, 2021