Cheap flights from Boston to Chicago

from as little as £171

13 nights in Chicago, departing Boston on 15 / Jan / 2025 with JetBlue (price found 2 hours ago)

Subject to availability, prices correct of the last 24 hours
Chicago

Cheap return flights from Boston to Chicago

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The Boston / Chicago route

All 1382 km of it

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Chicago flight facts

What you need to know

Alternative flights from the UK to Chicago

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Alternative flights from Boston

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Chicago

15 / Jan / 2025 is currently the lowest priced day of the year to fly the Boston/Chicago route. There are around seven flights on any given week from the UK to Chicago and the cheapest month to fly right now is January.

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Key facts about Chicago

How to get cheap flights from Boston to Chicago

Tips and advice from our flight experts

Your flight from Boston to Chicago should take about 2 hrs 55 mins. We've gone through all seven of the weekly flights to or via Chicago, operated by one airlines, to help you compare flight prices and times. At the moment, the cheapest flight is £171.

Or, if you're fairly flexible on dates, try to get a last minute-deal by regularly checking the Netflights website.

Chicago actually has one airports – but Chicago O'hare International Airport is normally the cheapest one to fly into. If you're not sure who to fly with from Boston, you might like to know that JetBlue is the most popular airline for this route.

If you can’t quite find what you’re looking for, try checking flight prices to other cities in the USA.

Other popular destinations near Chicago

Where other people are flying to

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