Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 72 with American Airlines.Best fare available on Aug 4, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

1 Aug
American Airlines
19:41BOS
01:41ORD
1 StopUSD 138VIEW DEAL
1 Aug
American Airlines
18:31BOS
22:00ORD
DirectUSD 135VIEW DEAL
1 Aug
American Airlines
05:10BOS
08:04ORD
DirectUSD 114VIEW DEAL
2 Aug
JetBlue Airways
08:07BOS
11:05ORD
DirectUSD 84VIEW DEAL
2 Aug
American Airlines
05:10BOS
08:04ORD
DirectUSD 114VIEW DEAL
2 Aug
United Airlines
07:19BOS
10:17ORD
DirectUSD 150VIEW DEAL
3 Aug
American Airlines
05:10BOS
08:04ORD
DirectUSD 113VIEW DEAL
4 Aug
American Airlines
05:10BOS
08:04ORD
DirectUSD 72VIEW DEAL
4 Aug
Frontier Airlines
11:52BOS
20:53ORD
1 StopUSD 123VIEW DEAL
5 Aug
American Airlines
10:28BOS
13:29ORD
DirectUSD 105VIEW DEAL

Boston to Chicago monthly flight fare trend

Aug
from USD 71
Sep
from USD 71
Oct
from USD 70
Nov
from USD 110
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

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