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

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Boston to Chicago Flight Deals

 

* All fares above were last found on:  .Fares are round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions

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:

Once you’re done sharing photos from your trip to Chicago, do not forget to share your Chicago experience with us through the CheapOair review section. Help and inspire other travelers by sharing your valuable opinion. Remember, your reviews can help us make our service better.

CheapOair Customer Reviews

Eugene OR

My trip was planned perfectly, from flight to accommodations. I'll be visiting again in the Spring and using CheapOair to plan again. Very satisfied! - Steven  Dec 12, 2024

Greece Getaway

My first experience with CheapOair was very good! The reservations made to fly to Greece had smooth connections at each airport. I was hoping for the ability to watch the reservation price and adjust it as the trip got closer, but once I locked in my reservation, the price couldn’t be changed. Text messages from them were clear and kept me informed on the flight plan! I would rate this experience as very good. - Bette  Dec 01, 2024

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