How to find the cheapest flight from
Chicago (CHI) to Massachusetts
How far in advance should I book a flight from Chicago to Massachusetts?
To save up to 23% on this flight, we recommend booking at least 26 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Massachusetts from $270 1-2 weeks out and tickets from $316 for flights departing within the next 72 hours.
One-way flights to Massachusetts from Chicago
The cheapest one-way flights from Chicago to Massachusetts
2:45 pm - 6:17 pm
2:16 pm - 5:33 pm
1:10 pm - 4:36 pm
Related info for your journey
Useful info, stats and facts about Chicago to Massachusetts flights.
Arrival points for flights from Chicago to Massachusetts
Destination information for Massachusetts
Things to know before you go. Useful info for your trip from Chicago to Massachusetts
Chicago Midway (MDW)
New Bedford (EWB)