Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 98 with United Airlines.Best fare available on Jul 15, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

11 Jul
JetBlue Airways
10:20BOS
13:16ORD
DirectUSD 146VIEW DEAL
15 Jul
United Airlines
06:00BOS
08:58ORD
DirectUSD 98VIEW DEAL
15 Jul
JetBlue Airways
17:10BOS
20:15ORD
DirectUSD 142VIEW DEAL
16 Jul
United Airlines
09:50BOS
12:43ORD
DirectUSD 106VIEW DEAL
17 Jul
United Airlines
09:50BOS
12:43ORD
DirectUSD 106VIEW DEAL
18 Jul
United Airlines
08:15BOS
11:12ORD
DirectUSD 99VIEW DEAL
19 Jul
JetBlue Airways
08:07BOS
11:05ORD
DirectUSD 147VIEW DEAL
25 Jul
American Airlines
05:10BOS
08:04ORD
DirectUSD 101VIEW DEAL
25 Jul
United Airlines
08:15BOS
11:12ORD
DirectUSD 98VIEW DEAL
30 Jul
United Airlines
06:00BOS
08:58ORD
DirectUSD 125VIEW DEAL

Boston to Chicago monthly flight fare trend

Jul
from USD 98
Aug
from USD 71
Sep
from USD 71
Oct
from USD 70
Nov
from USD 110
Dec
from USD 116

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