Flight Routes from Boston to Chicago Midway

Trip type

Our cheapest offers for flights from Boston to Chicago Midway

Here you can compare cheap flights from Boston (BOS) to Chicago Midway (MDW) 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 Chicago Midway. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Boston
Chicago Midway
Outbound
08/20/26
1 Stopover (ATL)
F93085, F92779
06h 12min
Return
08/25/26
1 Stopover (ATL)
F92144, F93086
12h 00min
Frontier Airlines
$280
found 2 days ago
Boston
Chicago Midway
Please note: transfer for connecting flight
Outbound
08/20/26
1 Stopover (ATL)
F93511, F92291
13h 59min
Return
08/25/26
1 Stopover (ATL)
F92292, F93086
18h 27min
Frontier Airlines
$318
found 2 days ago
Boston
Chicago Midway
Outbound
06/25/26
1 Stopover (ATL)
F93085, F92291
15h 06min
Return
06/30/26
1 Stopover (ATL)
F92144, F93512
11h 01min
Frontier Airlines ?
$466
Boston
Chicago Midway
Outbound
06/25/26
1 Stopover (ATL)
F93511, F92291
09h 24min
Return
06/30/26
1 Stopover (ATL)
F92144, F93512
11h 01min
Frontier Airlines
$589
Boston
Chicago Midway
Please note: transfer for connecting flight
Outbound
10/01/26
1 Stopover (TYS)
G41418, G41416
28h 17min
Return
10/11/26
1 Stopover (ATL)
F92144, F93512
21h 49min
Allegiant Air
$598
found 3 days ago
Boston
Chicago Midway
Please note: transfer for connecting flight
Outbound
06/25/26
1 Stopover (ATL)
F93511, F92291
09h 24min
Return
06/30/26
1 Stopover (YTZ)
PD2388, TS7356
05h 21min
Frontier Airlines
$642
Boston
Chicago Midway
Outbound
10/01/26
2 Stopovers (MEX, GDL)
AM0641, Y40140, Y41840
33h 44min
Return
10/11/26
3 Stopovers (ATL, BOG, EWR)
LA6114, LA6351, UA0269, UA0577
51h 00min
Aeroméxico, Volaris ?
$1,525
found 3 days ago
Boston
Chicago Midway
Outbound
06/25/26
1 Stopover (DTW)
DL1019, DL4684
04h 12min
Return
06/30/26
1 Stopover (ATL)
DL1063, DL0821
08h 56min
Delta Air Lines ?
$3,004
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Boston to Chicago Midway

Favorite airline: Frontier Airlines
The most popular airline for flights from Boston to Chicago Midway is Frontier Airlines.
Frontier Airlines
52 %
Delta
24 %
Porter Airlines
16 %
Cheapest weekday: Thursday
The cheapest days to fly on this route are Thursday.
Favourite connection: via Orlando
37 % of booked tickets on this route are for flights with a transfer in Orlando.
Route
bookings
1 stopover Orlando International Airport, FL
25h 34min, from $ 396
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from $ 217
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from $ 550
21 %

Important flight information

Flight information: Boston - Chicago Midway

Roundtrip from $ 279,98
Flight duration min. 02:45 / max. 06:55
Return flight duration min. 02:10/ max. 11:15
Distance 1383 km
Flights per week 23
Departure airport Airport Boston Logan International Airport, MA (BOS)
Arrival airport Airport Chicago Midway International Airport, IL (MDW)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Chicago Midway
Flight destinations with a similar price