Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 112 with Southwest Airlines.Best fare available on Sep 8, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

3 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 159VIEW DEAL
4 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 175VIEW DEAL
5 Sept
Southwest Airlines
07:55MDW
20:45BOS
2 StopUSD 171VIEW DEAL
5 Sept
Southwest Airlines
07:40MDW
10:00BOS
DirectUSD 189VIEW DEAL
6 Sept
Southwest Airlines
08:45MDW
11:15BOS
DirectUSD 147VIEW DEAL
7 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 121VIEW DEAL
8 Sept
Southwest Airlines
08:45MDW
11:15BOS
DirectUSD 112VIEW DEAL
8 Sept
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 120VIEW DEAL
8 Sept
Southwest Airlines
18:00MDW
20:25BOS
DirectUSD 176VIEW DEAL
9 Sept
Southwest Airlines
08:45MDW
11:15BOS
DirectUSD 155VIEW DEAL

Chicago to Boston monthly flight fare trend

Sep
from USD 99
Oct
from USD 111
Nov
from USD 113
Dec
from USD 121
Jan
No flights
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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