Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 82 with American Airlines.Best fare available on Jun 29, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

21 Jun
American Airlines
05:05BOS
08:03ORD
Direct$97VIEW DEAL
28 Jun
American Airlines
05:05BOS
08:03ORD
Direct$96VIEW DEAL
29 Jun
American Airlines
05:05BOS
08:03ORD
Direct$82VIEW DEAL
31 Jul
American Airlines
05:00BOS
07:55ORD
Direct$111VIEW DEAL
28 Sept
JetBlue Airways
17:00BOS
20:22ORD
Direct$108VIEW DEAL
22 Mar
Air Canada
14:45BOS
21:16ORD
1 Stop$511VIEW DEAL

Boston to Chicago monthly flight fare trend

Jun
from USD 82
Jul
from USD 111
Aug
No flights
Sep
from USD 108
Oct
No flights
Nov
No flights

Airport Details

Origin

Boston

Logan International Airport (BOS)

Boston, BOS
Zone

New York

Elev

20 ft

Destination

Chicago

Chicago O'Hare International Airport (ORD)

Chicago, ORD
Zone

Chicago

Elev

680 ft

Flights from Boston

Flights from Boston to AtlantaFlights from Boston to AustinFlights from Boston to CharlotteFlights from Boston to DenverFlights from Boston to DallasFlights from Boston to DetroitFlights from Boston to NewarkFlights from Boston to Fort LauderdaleFlights from Boston to HonoluluFlights from Boston to Washington