Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 98 with United Airlines.Best fare available on Jul 25, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

23 Jul
United Airlines
07:19BOS
10:17ORD
DirectUSD 135VIEW DEAL
25 Jul
American Airlines
05:10BOS
08:04ORD
DirectUSD 101VIEW DEAL
25 Jul
United Airlines
08:15BOS
11:12ORD
DirectUSD 98VIEW DEAL
27 Jul
United Airlines
10:35BOS
13:28ORD
DirectUSD 148VIEW DEAL
28 Jul
United Airlines
12:30BOS
15:23ORD
DirectUSD 108VIEW DEAL
30 Jul
United Airlines
06:00BOS
08:58ORD
DirectUSD 125VIEW DEAL
30 Jul
American Airlines
05:10BOS
08:04ORD
DirectUSD 111VIEW DEAL
30 Jul
United Airlines
20:15BOS
23:15ORD
DirectUSD 161VIEW DEAL
30 Jul
United Airlines
05:45BOS
10:36ORD
1 StopUSD 178VIEW DEAL
31 Jul
American Airlines
05:00BOS
07:55ORD
DirectUSD 111VIEW 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

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