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Recent Chicago Posts

Search Cheap Flights from Boston to Chicago

Take flights from BOS to CHI for less

5 ways to book cheap flights from Boston to Chicago

Roundtrip tickets: As per trends, round trip tickets are cheaper than one-way tickets. Book round trip flights from Boston to Chicago to save on plane tickets.

Loyalty Programs: Many airlines and online travel portals offer loyalty programs wherein passengers score points each time they travel. Redeem these points to save on plane tickets.

Mailing lists: Travel agencies and online travel portals send updates regarding upcoming discounts and sales. Subscribe to mailing lists to save on flights from BOS to CHI.

Multi-city flights: Book a multicity flight to save on tickets. It is often the case that direct flights are more expensive. You may look for a cheap stopover alternative and get to explore two destinations at the price of one.

Set Google Alerts: When looking for Boston to Chicago flights, browse through airfares and set alerts on Google for your top choices. You will receive a notification in case the airfare changes. As soon as the fare drops, you can book your cheap flight tickets.

Getting to know Chicago

Also known as the Windy City, Chicago is the third most populous city in the US. Located along the banks of the Lake Michigan, Chicago is famed for its vibrant art scene, thriving culinary scene, and spectacular architecture. The culturally rich city has a plethora of museums, performing art venues, art galleries, leafy parks, and much more. Chicago’s diversity is reflected in its many ethnic neighborhoods, namely, Puerto Rican Paseo Boricua, Little Vietnam, Little Italy, Little Seoul, and Chinatown. Food lovers must not forget to try the ethnic cuisines while strolling through these colorful neighborhoods. Music and theater enthusiasts can catch live performances at top venues such as Symphony Center, Lincoln Hall, Chicago Shakespeare Theater, and Jazz Showcase. Other major attractions in Chicago are Millennium Park, Navy Pier, Chicago Riverwalk and Lakefront Trail, Lincoln Park, 360 Chicago, and Michigan Avenue and the Magnificent Mile.

Popular Festivals and Events

Chicago hosts a number of annual festivals around the year. Few of the major festivals are Chicago Wine Fest (April), Chicago Blues Festival (June), 57th Street Art Fair (June), Chicago Food Truck Festival (July), Taste of Chicago (July), Chicago Craft Beer Festival (July), Lollapalooza Chicago (August), Bristol Renaissance Faire (August), Illinois State Fair (August), Chicago Hot Dog Fest (August), Chicago World Music Festival (September), Chicago Jazz Festival (September), and NYE Fireworks (December).

Best Time to Visit Chicago

Chicago is flooded with tourists during summer season due to amiable weather and a flurry of events. The best time to take flights from Boston to Chicago is from April to May and from September to October.

    Boston to Chicago Flight Route Facts

  • What is the cheapest return flight price from BOS to CHI?


  • What is the fare range for flights from BOS to CHI?

    $108 - $431

  • When does the earliest flight depart BOS?

    5:12AM United Airlines Flight #342

  • When does the latest flight depart CHI?

    9:00PM United Airlines Flight #913

  • Which is the busiest month to travel from Boston to Chicago?


  • Which is the least-busy month to travel from BOS to CHI?


  • What is the travel distance between Boston and Chicago?

    849 miles

  • How many weekly flights operate between BOS and CHI?

    There are 14 weekly flights between BOS and CHI.

  • How many daily flights fly between Boston and Chicago?

    There are 1 daily flights between BOS and CHI

  • Which is the busiest day in terms of passengers flying from BOS to CHI?


  • In last 30 days, what is the %age of CHI visitors who spent less than 3 days in the city?

    100.00 %

  • Which airport is located close to CHI?

    Midway International Airport

  • Which airport is located close to BOS?

    Logan International Airport

Chicago Reviews

Excellent agent

My agent was excellent!! The best so far, I would say. Well done!

- DARCY  Oct 19, 2019
Thoroughly professional

Taylor was like a breeze of fresh air; his way of explaining things was so professional. He knew what he was doing. You should not only increase his salary, but also you should understand that you are very blessed to have him as an advisor.

- Saeeda  Oct 18, 2019