Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 86 with American Airlines.Best fare available on Nov 26, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

13 Nov
Frontier Airlines
12:39BOS
19:45ORD
1 StopUSD 142VIEW DEAL
17 Nov
Frontier Airlines
12:15BOS
19:16ORD
1 StopUSD 130VIEW DEAL
17 Nov
American Airlines
12:33BOS
15:40ORD
DirectUSD 118VIEW DEAL
18 Nov
Frontier Airlines
12:39BOS
19:30ORD
1 StopUSD 141VIEW DEAL
19 Nov
Frontier Airlines
12:39BOS
19:45ORD
1 StopUSD 130VIEW DEAL
21 Nov
Frontier Airlines
11:06BOS
01:43ORD
1 StopUSD 136VIEW DEAL
26 Nov
American Airlines
12:08BOS
15:20ORD
DirectUSD 86VIEW DEAL
27 Nov
JetBlue Airways
07:55BOS
10:59ORD
DirectUSD 155VIEW DEAL
1 Dec
JetBlue Airways
14:40BOS
17:42ORD
DirectUSD 166VIEW DEAL
7 Dec
JetBlue Airways
14:40BOS
17:42ORD
DirectUSD 105VIEW DEAL

Boston to Chicago monthly flight fare trend

Nov
from USD 86
Dec
from USD 105
Jan
from USD 122
Feb
from USD 166
Mar
from USD 110
Apr
from USD 141

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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