Round trip

Boston to Chicago 🇺🇸

$314

Departs: Wed, Dec 23
Return: Fri, Jan 1
Stops: Direct
Airline: Southwest Airlines
Duration: 3h

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Other dates on this route

Cheapest one-way fare by departure dateLow $115 on Sun, Nov 15 · High $171

Work-hours calculator

This flight to Chicago costs you 20h 56m of work.

Your hourly pay$

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Prices come from fares travellers found in the last few days and can change at any time. Last updated Thu, 22 Oct 2026 16:17:21 GMT.

Boston to Chicago 🇺🇸

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