Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at SAR 333 with American Airlines.Best fare available on Sep 3, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

2 Sept
Frontier Airlines
12:45BOS
21:08ORD
1 StopSAR 477VIEW DEAL
3 Sept
American Airlines
08:27BOS
11:30ORD
DirectSAR 333VIEW DEAL
3 Sept
JetBlue Airways
05:01BOS
09:45ORD
1 StopSAR 389VIEW DEAL
3 Sept
United Airlines
12:27BOS
15:20ORD
DirectSAR 481VIEW DEAL
3 Sept
American Airlines
07:10BOS
10:16ORD
DirectSAR 444VIEW DEAL
3 Sept
JetBlue Airways
08:15BOS
11:11ORD
DirectSAR 707VIEW DEAL
4 Sept
American Airlines
06:14BOS
09:20ORD
DirectSAR 503VIEW DEAL
5 Sept
Frontier Airlines
12:45BOS
21:08ORD
1 StopSAR 470VIEW DEAL
5 Sept
American Airlines
19:17BOS
22:35ORD
DirectSAR 418VIEW DEAL
6 Sept
JetBlue Airways
16:30BOS
22:55ORD
1 StopSAR 392VIEW DEAL

Boston to Chicago monthly flight fare trend

Sep
from SAR 263
Oct
from SAR 259
Nov
from SAR 318
Dec
from SAR 414
Jan
from SAR 451
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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