Cheap flights from Chicago to Boston

Flights tailored to your budget

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How much is a flight from Chicago to Boston?

Depending on when you travel and how far in advance you book, fares between Chicago and Boston can differ a lot.

Select your dates to check current offers.

Low-cost airlines offer competitive fares, but often add charges for extra services. Keep that in mind when planning your trip. Also, midweek departures may offer better deals than weekends.

Best airport options between Chicago and Boston

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

  • Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
  • Airports in Boston: Boston - Logan is the sole airport currently available.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Flights from Chicago to Boston - Logan

Plan smarter: flights from Chicago to Boston

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to Boston.

How much does an airline ticket from Chicago to Boston cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to Boston.

How far is Chicago from Boston?

Chicago is about 1375 km from Boston.

What are the airports in Boston?

Boston has one airport: Boston - Logan.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Chicago to Boston?

This information is not available at the moment.

What is the cheapest month to fly from Chicago to Boston?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Boston?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Boston?

This information is not available at the moment.