Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at USD 106 with JetBlue Airways.Best fare available on Sep 6, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

5 Sept
Frontier Airlines
12:45BOS
21:08ORD
1 StopUSD 139VIEW DEAL
5 Sept
American Airlines
19:17BOS
22:35ORD
DirectUSD 113VIEW DEAL
6 Sept
JetBlue Airways
16:30BOS
22:55ORD
1 StopUSD 106VIEW DEAL
7 Sept
JetBlue Airways
05:01BOS
09:48ORD
1 StopUSD 106VIEW DEAL
7 Sept
United Airlines
08:05BOS
11:04ORD
DirectUSD 128VIEW DEAL
7 Sept
American Airlines
06:14BOS
09:20ORD
DirectUSD 192VIEW DEAL
8 Sept
United Airlines
18:42BOS
21:40ORD
DirectUSD 129VIEW DEAL
8 Sept
Frontier Airlines
12:45BOS
21:08ORD
1 StopUSD 173VIEW DEAL
9 Sept
American Airlines
13:34BOS
16:35ORD
DirectUSD 113VIEW DEAL
9 Sept
United Airlines
18:42BOS
21:40ORD
DirectUSD 205VIEW 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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