Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 104 with JetBlue Airways.Best fare available on Oct 1, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

30 Sept
American Airlines
13:34BOS
16:35ORD
DirectUSD 145VIEW DEAL
30 Sept
JetBlue Airways
07:00BOS
09:48ORD
DirectUSD 179VIEW DEAL
30 Sept
American Airlines
19:33BOS
00:15ORD
1 StopUSD 252VIEW DEAL
30 Sept
United Airlines
09:23BOS
12:15ORD
DirectUSD 153VIEW DEAL
1 Oct
JetBlue Airways
16:00BOS
23:06ORD
1 StopUSD 104VIEW DEAL
1 Oct
Frontier Airlines
11:17BOS
23:59ORD
1 StopUSD 139VIEW DEAL
1 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 156VIEW DEAL
2 Oct
Frontier Airlines
11:36BOS
23:59ORD
1 StopUSD 170VIEW DEAL
2 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 141VIEW DEAL
3 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 157VIEW DEAL

Boston to Chicago monthly flight fare trend

Sep
from USD 145
Oct
from USD 70
Nov
from USD 86
Dec
from USD 111
Jan
from USD 122
Feb
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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