Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 83 with Southwest Airlines.Best fare available on Aug 1, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

10 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectUSD 132VIEW DEAL
11 Jul
Southwest Airlines
05:25MDW
07:40BOS
DirectUSD 129VIEW DEAL
11 Jul
Southwest Airlines
17:45MDW
20:10BOS
DirectUSD 144VIEW DEAL
12 Jul
Southwest Airlines
05:15MDW
07:25BOS
DirectUSD 137VIEW DEAL
13 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectUSD 137VIEW DEAL
13 Jul
Southwest Airlines
09:20MDW
11:40BOS
DirectUSD 132VIEW DEAL
19 Jul
Southwest Airlines
05:15MDW
07:25BOS
DirectUSD 108VIEW DEAL
30 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectUSD 86VIEW DEAL
1 Aug
Southwest Airlines
17:45MDW
20:10BOS
DirectUSD 83VIEW DEAL
2 Aug
Southwest Airlines
05:15MDW
07:25BOS
DirectUSD 87VIEW DEAL

Chicago to Boston monthly flight fare trend

Jul
from USD 86
Aug
from USD 77
Sep
No flights
Oct
No flights
Nov
No flights
Dec
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

Flights from Chicago

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