Chicago to Boston
MDWBOS
Fly from Chicago to Boston starting at USD 108 with Southwest Airlines.
Best fare available on Jul 5, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to Boston cheapest flights this week
Chicago to Boston monthly flight fare trend
Jun
No flights
Jul
from USD 108
Aug
No flights
Sep
No flights
Oct
No flights
Nov
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
Boston
Logan International Airport (BOS)
Boston, BOS
Zone
New York
Elev
20 ft
Flights from Chicago
Flights from Chicago to AtlantaFlights from Chicago to AustinFlights from Chicago to CharlotteFlights from Chicago to DenverFlights from Chicago to DallasFlights from Chicago to DetroitFlights from Chicago to NewarkFlights from Chicago to Fort LauderdaleFlights from Chicago to HonoluluFlights from Chicago to Washington
