Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 77 with Southwest Airlines.Best fare available on Aug 19, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

19 Aug
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 77VIEW DEAL
20 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 134VIEW DEAL
20 Aug
Southwest Airlines
19:55MDW
07:00BOS
1 StopUSD 137VIEW DEAL
21 Aug
Southwest Airlines
19:55MDW
07:00BOS
1 StopUSD 129VIEW DEAL
22 Aug
Southwest Airlines
07:40MDW
10:00BOS
DirectUSD 180VIEW DEAL
23 Aug
Southwest Airlines
06:00MDW
08:15BOS
DirectUSD 121VIEW DEAL
24 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 150VIEW DEAL
25 Aug
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 125VIEW DEAL
26 Aug
Southwest Airlines
12:50MDW
15:10BOS
DirectUSD 147VIEW DEAL
27 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 155VIEW DEAL

Chicago to Boston monthly flight fare trend

Aug
from USD 77
Sep
from USD 75
Oct
from USD 111
Nov
No flights
Dec
from USD 121
Jan
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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