United is selling cheap flights from Boston to Chicago for as low as $48 return! That works out to a cost of just 2.8 Cents Per Mile for this 1700 mile journey.

The fare only includes carry-on luggage, so you need to pay extra if you want to check bags.

Our data shows the lowest prices are available in September 2020. See the link(s) below for dates and prices.

Sample date(s) with Skyscanner.com booking link

Sep 14 – Sep 17 ($48)


Sep 15 – Sep 19 ($48)


Sep 15 – Sep 22 ($48)


Sep 16 – Sep 19 ($49)


Sep 16 – Sep 20 ($48)


Sep 17 – Sep 20 ($49)


Sep 17 – Sep 22 ($49)


Sep 25 – Sep 28 ($49)


Oct 1 – Oct 4 ($48)


Oct 15 – Oct 22 ($48)

We post many cheap flights like this one from Boston to Chicago every single day, so have a look at our Travel Deals page, or check out the related posts below!

Note: Prices are valid at the time of publishing this post, but may change in the future.

COVID-19 Note: During these uncertain times, please make sure to check the relevant Coronavirus restrictions for your destination before you book and before you fly. We recommend also checking the refund policy of the airline, as well as purchasing travel insurance for your trip.

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