Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 99 with Southwest Airlines.Best fare available on Sep 16, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

11 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 124VIEW DEAL
11 Sept
Southwest Airlines
18:30MDW
20:55BOS
DirectUSD 166VIEW DEAL
12 Sept
Southwest Airlines
09:05MDW
11:25BOS
DirectUSD 119VIEW DEAL
14 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 167VIEW DEAL
16 Sept
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 99VIEW DEAL
16 Sept
Southwest Airlines
12:50MDW
15:10BOS
DirectUSD 184VIEW DEAL
17 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 166VIEW DEAL
18 Sept
Southwest Airlines
19:55MDW
07:00BOS
1 StopUSD 177VIEW DEAL
18 Sept
Southwest Airlines
18:30MDW
20:55BOS
DirectUSD 148VIEW DEAL
19 Sept
Southwest Airlines
07:40MDW
10:00BOS
DirectUSD 115VIEW DEAL

Chicago to Boston monthly flight fare trend

Sep
from USD 99
Oct
from USD 111
Nov
from USD 113
Dec
from USD 109
Jan
from USD 142
Feb
No flights

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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