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
04/29/25
direct
WN0576
02h 35min
Return
05/08/25
direct
WN0404
02h 15min
Southwest Airlines ?
$172
Boston
Chicago Midway
Pay attention to transfer at connecting flight
Outbound
09/19/25
1 Stopover (AVL)
G40226, G40513
08h 44min
Return
09/29/25
1 Stopover (TYS)
G43021, G41397
13h 27min
Allegiant Air
$297
Boston
Chicago Midway
Outbound
06/07/25
direct
WN1435
02h 35min
Return
06/23/25
direct
WN1427
02h 15min
Southwest Airlines ?
$183
found 3 days ago
Boston
Chicago Midway
Outbound
06/08/25
1 Stopover (TPA)
F91215, F93899
13h 36min
Return
06/12/25
1 Stopover (MCO)
F93854, F93348
27h 00min
Frontier Airlines
$240
Boston
Chicago Midway
Outbound
06/08/25
1 Stopover (TPA)
F91215, F93899
13h 36min
Return
06/12/25
1 Stopover (MCO)
F93854, F93348
27h 00min
Frontier Airlines
$250
Boston
Chicago Midway
Outbound
06/08/25
1 Stopover (SAV)
G41152, G41163
20h 44min
Return
06/12/25
1 Stopover (ATL)
F92144, F93512
10h 58min
Allegiant Air ?
$251
Boston
Chicago Midway
Outbound
04/29/25
1 Stopover (ATL)
B60896, F92143
17h 45min
Return
05/08/25
1 Stopover (ATL)
F92292, F93512
16h 22min
JetBlue Airways, Frontier Airlines ?
$294
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
06/07/25
2 Stopovers (EWR, ATL)
UA1308, UA2241, F92779
29h 09min
Return
06/23/25
1 Stopover (TYS)
G43025, G41397
17h 24min
United Airlines, Frontier Airlines ?
$353
found 3 days ago
Boston
Chicago Midway
Outbound
06/20/25
1 Stopover (ATL)
F93511, F92779
18h 55min
Return
07/19/25
2 Stopovers (ATL, MSP)
F92292, SY0356, SY0253
27h 59min
Frontier Airlines ?
$427
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 $ 171,64
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