Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 71 with JetBlue Airways.Best fare available on Sep 10, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

10 Sept
JetBlue Airways
06:55BOS
09:46ORD
DirectUSD 71VIEW DEAL
10 Sept
Frontier Airlines
11:17BOS
23:59ORD
1 StopUSD 100VIEW DEAL
10 Sept
United Airlines
18:42BOS
21:40ORD
DirectUSD 132VIEW DEAL
10 Sept
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 173VIEW DEAL
11 Sept
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 135VIEW DEAL
12 Sept
Frontier Airlines
12:54BOS
19:23ORD
1 StopUSD 143VIEW DEAL
13 Sept
United Airlines
07:05BOS
10:03ORD
DirectUSD 138VIEW DEAL
13 Sept
American Airlines
06:00BOS
09:10ORD
DirectUSD 178VIEW DEAL
15 Sept
American Airlines
12:05BOS
15:07ORD
DirectUSD 113VIEW DEAL
15 Sept
United Airlines
10:38BOS
13:29ORD
DirectUSD 86VIEW DEAL

Boston to Chicago monthly flight fare trend

Sep
from USD 71
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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