Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 89 with American Airlines.Best fare available on Aug 16, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

13 Aug
American Airlines
15:53BOS
19:04ORD
DirectUSD 103VIEW DEAL
14 Aug
American Airlines
08:27BOS
11:30ORD
DirectUSD 106VIEW DEAL
14 Aug
American Airlines
19:17BOS
22:35ORD
DirectUSD 121VIEW DEAL
14 Aug
JetBlue Airways
05:01BOS
09:52ORD
1 StopUSD 112VIEW DEAL
14 Aug
JetBlue Airways
08:15BOS
11:11ORD
DirectUSD 144VIEW DEAL
14 Aug
United Airlines
07:05BOS
10:04ORD
DirectUSD 157VIEW DEAL
15 Aug
United Airlines
15:30BOS
18:22ORD
DirectUSD 153VIEW DEAL
15 Aug
United Airlines
06:01BOS
09:00ORD
DirectUSD 160VIEW DEAL
16 Aug
United Airlines
07:05BOS
10:03ORD
DirectUSD 160VIEW DEAL
16 Aug
American Airlines
06:14BOS
09:20ORD
DirectUSD 89VIEW DEAL

Boston to Chicago monthly flight fare trend

Aug
from USD 71
Sep
from USD 71
Oct
from USD 70
Nov
from USD 86
Dec
from USD 116
Jan
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