Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at SAR 581 with Southwest Airlines.Best fare available on Oct 10, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

6 Oct
Southwest Airlines
07:50MDW
10:10BOS
DirectSAR 1,129VIEW DEAL
7 Oct
Southwest Airlines
09:10MDW
11:30BOS
DirectSAR 696VIEW DEAL
7 Oct
Southwest Airlines
18:10MDW
20:30BOS
DirectSAR 1,129VIEW DEAL
8 Oct
Southwest Airlines
05:30MDW
07:55BOS
DirectSAR 725VIEW DEAL
8 Oct
Southwest Airlines
11:00MDW
13:25BOS
DirectSAR 688VIEW DEAL
9 Oct
Southwest Airlines
14:45MDW
22:35BOS
1 StopSAR 1,240VIEW DEAL
9 Oct
Southwest Airlines
15:30MDW
17:50BOS
DirectSAR 1,066VIEW DEAL
10 Oct
Southwest Airlines
16:25MDW
18:50BOS
DirectSAR 581VIEW DEAL
10 Oct
Southwest Airlines
16:50MDW
21:10BOS
1 StopSAR 740VIEW DEAL
11 Oct
Southwest Airlines
05:00MDW
07:25BOS
DirectSAR 696VIEW DEAL

Chicago to Boston monthly flight fare trend

Oct
from SAR 363
Nov
from SAR 333
Dec
from SAR 403
Jan
from SAR 525
Feb
No flights
Mar
from SAR 2,250

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

Boston

Logan International Airport (BOS)

Boston, BOS
Zone

New York

Elev

20 ft

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