Flights from Chicago Midway to Boston

Our cheapest offers for flights from Chicago Midway to Boston

Here you can compare cheap flights from Chicago Midway (MDW) to Boston (BOS) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Boston. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Chicago Midway
Boston
Outbound
07/01/25
direct
WN3787
02h 10min
Return
07/06/25
1 Stopover (BNA)
WN1148, WN4010
04h 55min
Southwest Airlines ?
$248
Chicago Midway
Boston
Outbound
07/01/25
2 Stopovers (ATL, EWR)
F92144, UA1128, UA0577
26h 53min
Return
07/06/25
1 Stopover (TYS)
G41426, G43027
26h 14min
Frontier Airlines, United Airlines ?
$377
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago Midway to Boston

Favorite airline: Porter Airlines
Flight tickets on the route Chicago Midway – Boston are most frequently booked with Porter Airlines.
Porter Airlines
57 %
Delta
43 %
Favourite connection: via Toronto - City Centre
On this route, flights with a stopover in Toronto - City Centre are the most popular.
Route
bookings
1 stopover Toronto - City Centre Airport
09h 12min, from 498 $
57 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
08h 11min, from 355 $
29 %
1 stopover Detroit Metropolitan Wayne County Airport, MI
05h 44min, from 735 $
14 %

Important flight information

Flight information: Chicago Midway - Boston

Roundtrip from 247,67 $
Flight duration min. 02:10 / max. 11:15
Return flight duration min. 02:45/ max. 06:55
Distance 1383 km
Flights per week 23
Departure airport Airport Chicago Midway International Airport, IL (MDW)
Arrival airport Airport Boston Logan International Airport, MA (BOS)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Boston
Flight destinations with a similar price
Flight destinations with a similar price