Flights from Boston to Chicago Midway

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
07/08/25
direct
WN1435
02h 35min
Return
08/07/25
direct
WN3544
02h 20min
Southwest Airlines ?
$157
Boston
Chicago Midway
Pay attention to transfer at connecting flight
Outbound
10/18/25
3 Stopovers (FLL, PIT, PGD)
NK2887, NK0228, G41110, G42478
25h 35min
Return
11/17/25
1 Stopover (TYS)
G41432, G41397
16h 31min
Spirit Airlines, Allegiant Air
$264
Boston
Chicago Midway
Outbound
07/02/25
direct
WN1433
02h 40min
Return
07/25/25
direct
WN1011
02h 15min
Southwest Airlines ?
$173
Boston
Chicago Midway
Outbound
10/09/25
1 Stopover (MIA)
F91435, F92109
10h 43min
Return
11/01/25
1 Stopover (MIA)
F92110, F91436
18h 31min
Frontier Airlines
$249
Boston
Chicago Midway
Outbound
10/09/25
1 Stopover (MIA)
F91435, F92109
10h 43min
Return
11/01/25
1 Stopover (MIA)
F92110, F91436
18h 31min
Frontier Airlines
$260
Boston
Chicago Midway
Outbound
07/02/25
1 Stopover (DCA, BWI)
AA3240, F93087
11h 14min
Return
07/25/25
1 Stopover (VPS)
G43081, G41443
25h 49min
American Airlines, Frontier Airlines ?
$317
Boston
Chicago Midway
Outbound
08/28/25
1 Stopover (DTW)
DL1019, DL3858
04h 15min
Return
09/19/25
1 Stopover (MSP)
DL3795, DL1502
07h 25min
Delta Air Lines ?
$318
Boston
Chicago Midway
Outbound
10/18/25
2 Stopovers (MSP, VPS)
SY0254, SY1811, G43078
28h 47min
Return
11/17/25
1 Stopover (TYS)
G41432, G41397
16h 31min
Sun Country Airlines, Allegiant Air ?
$449
Boston
Chicago Midway
Outbound
07/08/25
1 Stopover (DCA, BWI)
B61955, F93087
26h 26min
Return
08/07/25
3 Stopovers (ATL, LHR, LGW, JFK)
VS2618, VS4044, AA6938, AA4659
35h 28min
JetBlue Airways, Frontier Airlines ?
$1,339
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 $ 156,95
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