Boston to Chicago

BOSORD

Fly from Boston to Chicago starting at SAR 385 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
DirectSAR 537VIEW DEAL
30 Sept
JetBlue Airways
07:00BOS
09:48ORD
DirectSAR 662VIEW DEAL
30 Sept
American Airlines
19:33BOS
00:15ORD
1 StopSAR 932VIEW DEAL
30 Sept
United Airlines
09:23BOS
12:15ORD
DirectSAR 566VIEW DEAL
1 Oct
JetBlue Airways
16:00BOS
23:06ORD
1 StopSAR 385VIEW DEAL
1 Oct
Frontier Airlines
11:17BOS
23:59ORD
1 StopSAR 625VIEW DEAL
1 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopSAR 577VIEW DEAL
2 Oct
Frontier Airlines
11:36BOS
23:59ORD
1 StopSAR 629VIEW DEAL
2 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopSAR 522VIEW DEAL
3 Oct
Frontier Airlines
12:54BOS
19:23ORD
1 StopSAR 581VIEW DEAL

Boston to Chicago monthly flight fare trend

Sep
from SAR 537
Oct
from SAR 259
Nov
from SAR 318
Dec
from SAR 411
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

Flights from Boston

Flights from Boston to AtlantaFlights from Boston to AustinFlights from Boston to CharlotteFlights from Boston to DenverFlights from Boston to DallasFlights from Boston to DetroitFlights from Boston to NewarkFlights from Boston to Fort LauderdaleFlights from Boston to HonoluluFlights from Boston to Washington